|
|
char = I;code = 73
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = e;code = 101
char = l;code = 108
char = u;code = 117
char = c;code = 99
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char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = .;code = 46
result sql = Isolation and structural elucidation of cyclopentynafil and N-octylnortadalafil found in a dietary supplement.
Isolation and structural elucidation of cyclopentynafil and N-octylnortadalafil found in a dietary supplement.char = A;code = 65
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
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char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = );code = 41
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
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char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
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char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
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char = l;code = 108
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = ;code = 32
char = w;code = 119
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char = r;code = 114
char = e;code = 101
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char = i;code = 105
char = s;code = 115
char = o;code = 111
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char = e;code = 101
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char = r;code = 114
char = o;code = 111
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char = a;code = 97
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char = y;code = 121
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = i;code = 105
char = l;code = 108
char = l;code = 108
char = e;code = 101
char = g;code = 103
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = k;code = 107
char = e;code = 101
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = l;code = 108
char = e;code = 101
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char = d;code = 100
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char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
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char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
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char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
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char = a;code = 97
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char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
char = -;code = 45
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char = o;code = 111
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char = o;code = 111
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char = e;code = 101
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = r;code = 114
char = a;code = 97
char = y;code = 121
char = ;code = 32
char = (;code = 40
char = P;code = 80
char = D;code = 68
char = A;code = 65
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char = ,;code = 44
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char = L;code = 76
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char = M;code = 77
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char = i;code = 105
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char = s;code = 115
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char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = M;code = 77
char = S;code = 83
char = ,;code = 44
char = ;code = 32
char = N;code = 78
char = M;code = 77
char = R;code = 82
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
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char = l;code = 108
char = a;code = 97
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char = d;code = 100
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char = c;code = 99
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char = r;code = 114
char = o;code = 111
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char = m;code = 109
char = ;code = 32
char = (;code = 40
char = C;code = 67
char = D;code = 68
char = );code = 41
char = .;code = 46
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char = T;code = 84
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
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char = p;code = 112
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char = e;code = 101
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char = n;code = 110
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char = d;code = 100
char = ;code = 32
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char = o;code = 111
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char = b;code = 98
char = e;code = 101
char = ;code = 32
char = 5;code = 53
char = -;code = 45
char = [;code = 91
char = 2;code = 50
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char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 5;code = 53
char = -;code = 45
char = (;code = 40
char = 4;code = 52
char = -;code = 45
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
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char = l;code = 108
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char = 1;code = 49
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char = a;code = 97
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char = g;code = 103
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char = a;code = 97
char = s;code = 115
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char = (;code = 40
char = P;code = 80
char = D;code = 68
char = E;code = 69
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char = 5;code = 53
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char = i;code = 105
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char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = r;code = 114
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = p;code = 112
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = Q;code = 81
char = u;code = 117
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = t;code = 116
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = y;code = 121
char = s;code = 115
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = h;code = 104
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = 1;code = 49
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 2;code = 50
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = 1;code = 49
char = 3;code = 51
char = 0;code = 48
char = ;code = 32
char = m;code = 109
char = g;code = 103
char = /;code = 47
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = t;code = 116
char = ;code = 32
char = (;code = 40
char = 3;code = 51
char = 0;code = 48
char = 1;code = 49
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = g;code = 103
char = );code = 41
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = 2;code = 50
char = 7;code = 55
char = ;code = 32
char = m;code = 109
char = g;code = 103
char = /;code = 47
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = t;code = 116
char = ;code = 32
char = (;code = 40
char = 6;code = 54
char = 4;code = 52
char = .;code = 46
char = 1;code = 49
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = g;code = 103
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = .;code = 46
char = <;code = 60
char = b;code = 98
char = r;code = 114
char = /;code = 47
char = >;code = 62
result sql = A new sildenafil analogue, cyclopentynafil (1) and a new tadalafil analogue, N-octylnortadalafil (2) were isolated from a dietary supplement illegally marketed for erectile dysfunction. The structures of the sildenafil and tadalafil analogues were elucidated by using HPLC-photodiode array (PDA), LC-MS, high-resolution MS, NMR and circular dichroism (CD). These compounds were determined to be 5-[2-ethoxy-5-(4-cyclopentylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one and (6R,12aR)-2-octyl-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, respectively. Recently, a large number of phosphodiesterase-5 (PDE-5) inhibitors, including their analogues, have been isolated from dietary supplements, while cyclopentynafil and N-octylnortadalafil are the first compounds reported to be new sildenafil and tadalafil analogues, respectively. Quantitative HPLC analysis showed that the contents of 1 and 2 in the product were about 130 mg/tablet (301 microg/mg) and about 27 mg/tablet (64.1 microg/mg), respectively.
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = e;code = 101
char = l;code = 108
char = u;code = 117
char = c;code = 99
char = i;code = 105
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = .;code = 46
result sql = Isolation and structural elucidation of cyclopentynafil and N-octylnortadalafil found in a dietary supplement.
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = );code = 41
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = i;code = 105
char = l;code = 108
char = l;code = 108
char = e;code = 101
char = g;code = 103
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = k;code = 107
char = e;code = 101
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = y;code = 121
char = s;code = 115
char = f;code = 102
char = u;code = 117
char = n;code = 110
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = e;code = 101
char = l;code = 108
char = u;code = 117
char = c;code = 99
char = i;code = 105
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
char = -;code = 45
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = d;code = 100
char = i;code = 105
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = r;code = 114
char = a;code = 97
char = y;code = 121
char = ;code = 32
char = (;code = 40
char = P;code = 80
char = D;code = 68
char = A;code = 65
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = L;code = 76
char = C;code = 67
char = -;code = 45
char = M;code = 77
char = S;code = 83
char = ,;code = 44
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = u;code = 117
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = M;code = 77
char = S;code = 83
char = ,;code = 44
char = ;code = 32
char = N;code = 78
char = M;code = 77
char = R;code = 82
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = i;code = 105
char = r;code = 114
char = c;code = 99
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = r;code = 114
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = h;code = 104
char = r;code = 114
char = o;code = 111
char = i;code = 105
char = s;code = 115
char = m;code = 109
char = ;code = 32
char = (;code = 40
char = C;code = 67
char = D;code = 68
char = );code = 41
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = ;code = 32
char = 5;code = 53
char = -;code = 45
char = [;code = 91
char = 2;code = 50
char = -;code = 45
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 5;code = 53
char = -;code = 45
char = (;code = 40
char = 4;code = 52
char = -;code = 45
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = p;code = 112
char = i;code = 105
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = z;code = 122
char = i;code = 105
char = n;code = 110
char = -;code = 45
char = 1;code = 49
char = -;code = 45
char = y;code = 121
char = l;code = 108
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = o;code = 111
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = );code = 41
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = ];code = 93
char = -;code = 45
char = 1;code = 49
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
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char = u;code = 117
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char = b;code = 98
char = e;code = 101
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char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
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char = o;code = 111
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = o;code = 111
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char = i;code = 105
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
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char = s;code = 115
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char = ;code = 32
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char = E;code = 69
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char = 5;code = 53
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char = ;code = 32
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char = b;code = 98
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char = h;code = 104
char = e;code = 101
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char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
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char = u;code = 117
char = e;code = 101
char = s;code = 115
char = ,;code = 44
char = ;code = 32
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char = v;code = 118
char = e;code = 101
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = e;code = 101
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char = s;code = 115
char = o;code = 111
char = l;code = 108
char = a;code = 97
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char = d;code = 100
char = ;code = 32
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char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = s;code = 115
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char = p;code = 112
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = w;code = 119
char = h;code = 104
char = i;code = 105
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = c;code = 99
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = y;code = 121
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = r;code = 114
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = p;code = 112
char = o;code = 111
char = r;code = 114
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = w;code = 119
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = d;code = 100
char = a;code = 97
char = l;code = 108
char = a;code = 97
char = f;code = 102
char = i;code = 105
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = u;code = 117
char = e;code = 101
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
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char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
char = .;code = 46
char = ;code = 32
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char = u;code = 117
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = t;code = 116
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = y;code = 121
char = s;code = 115
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = h;code = 104
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
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char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
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char = e;code = 101
char = n;code = 110
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char = f;code = 102
char = ;code = 32
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char = ;code = 32
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char = d;code = 100
char = ;code = 32
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char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
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char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
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char = l;code = 108
char = e;code = 101
char = t;code = 116
char = ;code = 32
char = (;code = 40
char = 3;code = 51
char = 0;code = 48
char = 1;code = 49
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = g;code = 103
char = );code = 41
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = 2;code = 50
char = 7;code = 55
char = ;code = 32
char = m;code = 109
char = g;code = 103
char = /;code = 47
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = t;code = 116
char = ;code = 32
char = (;code = 40
char = 6;code = 54
char = 4;code = 52
char = .;code = 46
char = 1;code = 49
char = ;code = 32
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = /;code = 47
char = m;code = 109
char = g;code = 103
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = y;code = 121
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result sql = A new sildenafil analogue, cyclopentynafil (1) and a new tadalafil analogue, N-octylnortadalafil (2) were isolated from a dietary supplement illegally marketed for erectile dysfunction. The structures of the sildenafil and tadalafil analogues were elucidated by using HPLC-photodiode array (PDA), LC-MS, high-resolution MS, NMR and circular dichroism (CD). These compounds were determined to be 5-[2-ethoxy-5-(4-cyclopentylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one and (6R,12aR)-2-octyl-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, respectively. Recently, a large number of phosphodiesterase-5 (PDE-5) inhibitors, including their analogues, have been isolated from dietary supplements, while cyclopentynafil and N-octylnortadalafil are the first compounds reported to be new sildenafil and tadalafil analogues, respectively. Quantitative HPLC analysis showed that the contents of 1 and 2 in the product were about 130 mg/tablet (301 microg/mg) and about 27 mg/tablet (64.1 microg/mg), respectively.
Publication: Chem. Pharm. Bull. 2009 Feb ;57(2)::185-9.
Publication Date: 2009 Feb
Study Author(s): Hasegawa, Takashi;Takahashi, Kazunaga;Saijo, Masaaki;Ishii, Toshiyasu;Nagata, Tomoko;Kurihara, Masaaki;Haishima, Yuji;Goda, Yukihiro;Kawahara, Nobuo;
Institution: Chiba Prefectural Institute of Public Health, Chuo-ku, Japan.
Shortcut link to this study:
Publication Date: 2009 Feb
Study Author(s): Hasegawa, Takashi;Takahashi, Kazunaga;Saijo, Masaaki;Ishii, Toshiyasu;Nagata, Tomoko;Kurihara, Masaaki;Haishima, Yuji;Goda, Yukihiro;Kawahara, Nobuo;
Institution: Chiba Prefectural Institute of Public Health, Chuo-ku, Japan.
Shortcut link to this study:
A new sildenafil analogue, cyclopentynafil (1) and a new tadalafil analogue, N-octylnortadalafil (2) were isolated from a dietary supplement illegally marketed for erectile dysfunction. The structures of the sildenafil and tadalafil analogues were elucidated by using HPLC-photodiode array (PDA), LC-MS, high-resolution MS, NMR and circular dichroism (CD). These compounds were determined to be 5-[2-ethoxy-5-(4-cyclopentylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one and (6R,12aR)-2-octyl-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, respectively. Recently, a large number of phosphodiesterase-5 (PDE-5) inhibitors, including their analogues, have been isolated from dietary supplements, while cyclopentynafil and N-octylnortadalafil are the first compounds reported to be new sildenafil and tadalafil analogues, respectively. Quantitative HPLC analysis showed that the contents of 1 and 2 in the product were about 130 mg/tablet (301 microg/mg) and about 27 mg/tablet (64.1 microg/mg), respectively.
PMID: 19182409
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