|
|
char = A;code = 65
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result sql = Aporphines. 31. Synthesis and antitumor activity of aporphine nitrogen mustards.
Aporphines. 31. Synthesis and antitumor activity of aporphine nitrogen mustards.char = A;code = 65
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char = v;code = 118
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result sql = A series of aporphine nitrogen mustards and their congeners (1b-g) has been prepared. N-[[Bis(2-chloroethyl)-amino]-2,11-dihyroxy-10-methoxynoraporphine (1b) and its mono- and diacetyl ester derivatives (1c-d) were prepared from N-(chloroacetyl)-2,11-diacetoxy-10-methoxynoraporphine (2). Reaction of 2 with diethanolamine under various conditions and different solvents resulted in the corresponding N-[[bis(2-hydroxyethyl)amino]acetyl] precursors, which were subsequently treated with SOCl2 to yield the target compounds. N-(2-Choroethyl)norapocodeine (1e) was obtained from the chlorination of N-(2-hydroxyethyl)norapocodeine (9) with SOCl2. Prolonging such treatment was found to result in the formation of N-[2-(chloroethoxy)ethyl]norapocodeine (1f) at the expense of 1e. N-[[[N'-(2-Chloroethyl)carbamyl]oxy]ethyl]norapocodeine (1g) and its 11-(2-chloroethyl)carbamyl derivative (1h) were also prepared. All the double-armed aporphine amide nitrogen mustards (ab-d) were found to have antitumor activity. The single-armed aporphine nitrogen mustard (1e) was also active in P388 but the activity was less than that observed with 1b-d. The lead compound 1a was inactive in the LE1210 and P388 systems at the doses tested. Similarly, the two aporphine mustard congeners (1f,g) were also inactive in the P388 system. All the activity was observed in the intraperitoneally innoculated tumor systems.
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char = p;code = 112
char = h;code = 104
char = i;code = 105
char = n;code = 110
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char = s;code = 115
char = .;code = 46
char = ;code = 32
char = 3;code = 51
char = 1;code = 49
char = .;code = 46
char = ;code = 32
char = S;code = 83
char = y;code = 121
char = n;code = 110
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = i;code = 105
char = s;code = 115
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char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
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char = t;code = 116
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char = c;code = 99
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char = i;code = 105
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result sql = Aporphines. 31. Synthesis and antitumor activity of aporphine nitrogen mustards.
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char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = );code = 41
char = -;code = 45
char = 2;code = 50
char = ,;code = 44
char = 1;code = 49
char = 1;code = 49
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 1;code = 49
char = 0;code = 48
char = -;code = 45
char = m;code = 109
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 = n;code = 110
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = r;code = 114
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = .;code = 46
char = ;code = 32
char = R;code = 82
char = e;code = 101
char = a;code = 97
char = c;code = 99
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 = 2;code = 50
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = v;code = 118
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = v;code = 118
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = e;code = 101
char = d;code = 100
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 = c;code = 99
char = o;code = 111
char = r;code = 114
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = p;code = 112
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = [;code = 91
char = [;code = 91
char = b;code = 98
char = i;code = 105
char = s;code = 115
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = );code = 41
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = o;code = 111
char = ];code = 93
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = ];code = 93
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = e;code = 101
char = c;code = 99
char = u;code = 117
char = r;code = 114
char = s;code = 115
char = o;code = 111
char = r;code = 114
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = w;code = 119
char = h;code = 104
char = i;code = 105
char = c;code = 99
char = h;code = 104
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = b;code = 98
char = s;code = 115
char = e;code = 101
char = q;code = 113
char = u;code = 117
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = S;code = 83
char = O;code = 79
char = C;code = 67
char = l;code = 108
char = 2;code = 50
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = y;code = 121
char = i;code = 105
char = e;code = 101
char = l;code = 108
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = g;code = 103
char = e;code = 101
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 = 46
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = C;code = 67
char = h;code = 104
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = );code = 41
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = c;code = 99
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = e;code = 101
char = );code = 41
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = b;code = 98
char = t;code = 116
char = a;code = 97
char = i;code = 105
char = n;code = 110
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 = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
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 = N;code = 78
char = -;code = 45
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = );code = 41
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = c;code = 99
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 9;code = 57
char = );code = 41
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = S;code = 83
char = O;code = 79
char = C;code = 67
char = l;code = 108
char = 2;code = 50
char = .;code = 46
char = ;code = 32
char = P;code = 80
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = o;code = 111
char = n;code = 110
char = g;code = 103
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = c;code = 99
char = h;code = 104
char = ;code = 32
char = t;code = 116
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
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 = t;code = 116
char = o;code = 111
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
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 = f;code = 102
char = o;code = 111
char = r;code = 114
char = m;code = 109
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 = N;code = 78
char = -;code = 45
char = [;code = 91
char = 2;code = 50
char = -;code = 45
char = (;code = 40
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = o;code = 111
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 = 41
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = ];code = 93
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = c;code = 99
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = f;code = 102
char = );code = 41
char = ;code = 32
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 = e;code = 101
char = x;code = 120
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = 1;code = 49
char = e;code = 101
char = .;code = 46
char = ;code = 32
char = N;code = 78
char = -;code = 45
char = [;code = 91
char = [;code = 91
char = [;code = 91
char = N;code = 78
char = ';code = 39
char = -;code = 45
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = C;code = 67
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = );code = 41
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = b;code = 98
char = a;code = 97
char = m;code = 109
char = y;code = 121
char = l;code = 108
char = ];code = 93
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = ];code = 93
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = ];code = 93
char = n;code = 110
char = o;code = 111
char = r;code = 114
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = c;code = 99
char = o;code = 111
char = d;code = 100
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 1;code = 49
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 = i;code = 105
char = t;code = 116
char = s;code = 115
char = ;code = 32
char = 1;code = 49
char = 1;code = 49
char = -;code = 45
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = );code = 41
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = b;code = 98
char = a;code = 97
char = m;code = 109
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = h;code = 104
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 = a;code = 97
char = l;code = 108
char = s;code = 115
char = o;code = 111
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = e;code = 101
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = .;code = 46
char = ;code = 32
char = A;code = 65
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
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char = d;code = 100
char = o;code = 111
char = u;code = 117
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = -;code = 45
char = a;code = 97
char = r;code = 114
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = r;code = 114
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = d;code = 100
char = e;code = 101
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char = n;code = 110
char = i;code = 105
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = s;code = 115
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = a;code = 97
char = b;code = 98
char = -;code = 45
char = d;code = 100
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 = f;code = 102
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = h;code = 104
char = a;code = 97
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = t;code = 116
char = u;code = 117
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
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 = i;code = 105
char = n;code = 110
char = g;code = 103
char = l;code = 108
char = e;code = 101
char = -;code = 45
char = a;code = 97
char = r;code = 114
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = p;code = 112
char = o;code = 111
char = r;code = 114
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = n;code = 110
char = i;code = 105
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = s;code = 115
char = t;code = 116
char = a;code = 97
char = r;code = 114
char = d;code = 100
char = ;code = 32
char = (;code = 40
char = 1;code = 49
char = e;code = 101
char = );code = 41
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = P;code = 80
char = 3;code = 51
char = 8;code = 56
char = 8;code = 56
char = ;code = 32
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = l;code = 108
char = e;code = 101
char = s;code = 115
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = o;code = 111
char = b;code = 98
char = s;code = 115
char = e;code = 101
char = r;code = 114
char = v;code = 118
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = 1;code = 49
char = b;code = 98
char = -;code = 45
char = d;code = 100
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = l;code = 108
char = e;code = 101
char = a;code = 97
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
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char = s;code = 115
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char = ;code = 32
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char = o;code = 111
char = r;code = 114
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = s;code = 115
char = t;code = 116
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char = r;code = 114
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char = ;code = 32
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char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = o;code = 111
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char = s;code = 115
char = e;code = 101
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char = v;code = 118
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = i;code = 105
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char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = t;code = 116
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char = l;code = 108
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char = t;code = 116
char = e;code = 101
char = d;code = 100
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char = t;code = 116
char = u;code = 117
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = s;code = 115
char = y;code = 121
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = m;code = 109
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result sql = A series of aporphine nitrogen mustards and their congeners (1b-g) has been prepared. N-[[Bis(2-chloroethyl)-amino]-2,11-dihyroxy-10-methoxynoraporphine (1b) and its mono- and diacetyl ester derivatives (1c-d) were prepared from N-(chloroacetyl)-2,11-diacetoxy-10-methoxynoraporphine (2). Reaction of 2 with diethanolamine under various conditions and different solvents resulted in the corresponding N-[[bis(2-hydroxyethyl)amino]acetyl] precursors, which were subsequently treated with SOCl2 to yield the target compounds. N-(2-Choroethyl)norapocodeine (1e) was obtained from the chlorination of N-(2-hydroxyethyl)norapocodeine (9) with SOCl2. Prolonging such treatment was found to result in the formation of N-[2-(chloroethoxy)ethyl]norapocodeine (1f) at the expense of 1e. N-[[[N'-(2-Chloroethyl)carbamyl]oxy]ethyl]norapocodeine (1g) and its 11-(2-chloroethyl)carbamyl derivative (1h) were also prepared. All the double-armed aporphine amide nitrogen mustards (ab-d) were found to have antitumor activity. The single-armed aporphine nitrogen mustard (1e) was also active in P388 but the activity was less than that observed with 1b-d. The lead compound 1a was inactive in the LE1210 and P388 systems at the doses tested. Similarly, the two aporphine mustard congeners (1f,g) were also inactive in the P388 system. All the activity was observed in the intraperitoneally innoculated tumor systems.
Publication: J. Med. Chem. 1980 Sep ;23(9)::1008-13.
Publication Date: 1980 Sep
Study Author(s): Neumeyer, J L;Granchelli, F E;Filer, C N;Soloway, A H;Law, S J;
Institution:
Shortcut link to this study:
Publication Date: 1980 Sep
Study Author(s): Neumeyer, J L;Granchelli, F E;Filer, C N;Soloway, A H;Law, S J;
Institution:
Shortcut link to this study:
A series of aporphine nitrogen mustards and their congeners (1b-g) has been prepared. N-[[Bis(2-chloroethyl)-amino]-2,11-dihyroxy-10-methoxynoraporphine (1b) and its mono- and diacetyl ester derivatives (1c-d) were prepared from N-(chloroacetyl)-2,11-diacetoxy-10-methoxynoraporphine (2). Reaction of 2 with diethanolamine under various conditions and different solvents resulted in the corresponding N-[[bis(2-hydroxyethyl)amino]acetyl] precursors, which were subsequently treated with SOCl2 to yield the target compounds. N-(2-Choroethyl)norapocodeine (1e) was obtained from the chlorination of N-(2-hydroxyethyl)norapocodeine (9) with SOCl2. Prolonging such treatment was found to result in the formation of N-[2-(chloroethoxy)ethyl]norapocodeine (1f) at the expense of 1e. N-[[[N'-(2-Chloroethyl)carbamyl]oxy]ethyl]norapocodeine (1g) and its 11-(2-chloroethyl)carbamyl derivative (1h) were also prepared. All the double-armed aporphine amide nitrogen mustards (ab-d) were found to have antitumor activity. The single-armed aporphine nitrogen mustard (1e) was also active in P388 but the activity was less than that observed with 1b-d. The lead compound 1a was inactive in the LE1210 and P388 systems at the doses tested. Similarly, the two aporphine mustard congeners (1f,g) were also inactive in the P388 system. All the activity was observed in the intraperitoneally innoculated tumor systems.
PMID: 7411543
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