|
|
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char = g;code = 103
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result sql = New pyridone, thioxopyridine, pyrazolopyridine and pyridine derivatives that modulate inflammatory mediators in stimulated RAW 264.7 murine macrophage.
New pyridone, thioxopyridine, pyrazolopyridine and pyridine derivatives that modulate inflammatory mediators in stimulated RAW 264.7 murine macrophage.char = T;code = 84
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result sql = The reaction of 2-acetyl-5,6,7,8-tetrahydronaphthalene 1 with some aldehydes was conducted in the presence of ethyl cyanoacetate and ammonium acetate, yielded the cyanopyridones 2a-c, which react with phosphorous pentasulphide to afford the corresponding thioxopyridine derivatives 3a-c, respectively. Compounds 2a,b were converted to 2-chloropyridine derivatives 4a,b by heating with phosphorous oxychloride and phosphorous pentachloride, which were fused with hydrazine hydrate and benzyl amine to afford the corresponding pyrazolopyridine 5a,b and cyanopyridine derivatives 6a,b respectively. Compounds 2a,b also afforded 3-cyanopyridinyl oxy acetic acid ethyl ester 7a,b by reaction with ethyl bromoacetate in dry acetone in the presence of anhydrous potassium carbonate, which upon condensation with hydrazine hydrate gave the corresponding acid hydrazide 8a,b and with benzyl amine gave the corresponding acetamide 9a,b. We investigated the effect of those new compounds on the macrophage growth, macrophage binding affinity to fluorescein isothiocyanate-conjugated bacterial lipoopolysaccharide (FITC-LPS), phagocytosis of FITC-zymosan, and radical scavenging affinity against OH(), ROO*, and O(2)(-)*, in addition to their influence of the inflammatory mediators [nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), prostaglandin E-2 (PGE-2), cycloxygenase-2 (COX-2), and 5-lipoxygenase (5-LO)] in LPS-stimulated macrophages. The findings revealed that the derivatives 2b, 3b, 5a, 7b, 9a and 9b can be recognized as promising multi-potent anti-inflammatory agents.
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char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
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 = s;code = 115
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = f;code = 102
char = l;code = 108
char = a;code = 97
char = m;code = 109
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = m;code = 109
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = R;code = 82
char = A;code = 65
char = W;code = 87
char = ;code = 32
char = 2;code = 50
char = 6;code = 54
char = 4;code = 52
char = .;code = 46
char = 7;code = 55
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = .;code = 46
result sql = New pyridone, thioxopyridine, pyrazolopyridine and pyridine derivatives that modulate inflammatory mediators in stimulated RAW 264.7 murine macrophage.
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = r;code = 114
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 = 45
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 = 45
char = 5;code = 53
char = ,;code = 44
char = 6;code = 54
char = ,;code = 44
char = 7;code = 55
char = ,;code = 44
char = 8;code = 56
char = -;code = 45
char = t;code = 116
char = e;code = 101
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = a;code = 97
char = p;code = 112
char = h;code = 104
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = l;code = 108
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = 1;code = 49
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 = 115
char = o;code = 111
char = m;code = 109
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = u;code = 117
char = c;code = 99
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 = p;code = 112
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = m;code = 109
char = m;code = 109
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = y;code = 121
char = i;code = 105
char = e;code = 101
char = l;code = 108
char = d;code = 100
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = o;code = 111
char = n;code = 110
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = 2;code = 50
char = a;code = 97
char = -;code = 45
char = c;code = 99
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 = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = a;code = 97
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = p;code = 112
char = h;code = 104
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = f;code = 102
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = d;code = 100
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 = t;code = 116
char = h;code = 104
char = i;code = 105
char = o;code = 111
char = x;code = 120
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
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 = s;code = 115
char = ;code = 32
char = 3;code = 51
char = a;code = 97
char = -;code = 45
char = c;code = 99
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 = C;code = 67
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 = 2;code = 50
char = a;code = 97
char = ,;code = 44
char = b;code = 98
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = v;code = 118
char = e;code = 101
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 = 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 = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
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 = s;code = 115
char = ;code = 32
char = 4;code = 52
char = a;code = 97
char = ,;code = 44
char = b;code = 98
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = h;code = 104
char = e;code = 101
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = x;code = 120
char = y;code = 121
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 = d;code = 100
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = a;code = 97
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 = d;code = 100
char = e;code = 101
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 = f;code = 102
char = u;code = 117
char = s;code = 115
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 = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = a;code = 97
char = z;code = 122
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = n;code = 110
char = z;code = 122
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = a;code = 97
char = f;code = 102
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = d;code = 100
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 = p;code = 112
char = y;code = 121
char = r;code = 114
char = a;code = 97
char = z;code = 122
char = o;code = 111
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = 5;code = 53
char = a;code = 97
char = ,;code = 44
char = b;code = 98
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
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 = s;code = 115
char = ;code = 32
char = 6;code = 54
char = a;code = 97
char = ,;code = 44
char = b;code = 98
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 = C;code = 67
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 = 2;code = 50
char = a;code = 97
char = ,;code = 44
char = b;code = 98
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 = f;code = 102
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = d;code = 100
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = 3;code = 51
char = -;code = 45
char = c;code = 99
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = i;code = 105
char = d;code = 100
char = ;code = 32
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = 7;code = 55
char = a;code = 97
char = ,;code = 44
char = b;code = 98
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = r;code = 114
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 = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = ;code = 32
char = b;code = 98
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = o;code = 111
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = d;code = 100
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = o;code = 111
char = n;code = 110
char = e;code = 101
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 = e;code = 101
char = s;code = 115
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = t;code = 116
char = a;code = 97
char = s;code = 115
char = s;code = 115
char = i;code = 105
char = u;code = 117
char = m;code = 109
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = b;code = 98
char = o;code = 111
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = e;code = 101
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 = u;code = 117
char = p;code = 112
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = n;code = 110
char = s;code = 115
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = a;code = 97
char = z;code = 122
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = a;code = 97
char = v;code = 118
char = e;code = 101
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
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char = o;code = 111
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char = n;code = 110
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char = a;code = 97
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char = d;code = 100
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char = y;code = 121
char = d;code = 100
char = r;code = 114
char = a;code = 97
char = z;code = 122
char = i;code = 105
char = d;code = 100
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char = a;code = 97
char = n;code = 110
char = d;code = 100
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char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = b;code = 98
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char = i;code = 105
char = n;code = 110
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char = ;code = 32
char = g;code = 103
char = a;code = 97
char = v;code = 118
char = e;code = 101
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
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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 = a;code = 97
char = c;code = 99
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = m;code = 109
char = i;code = 105
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char = e;code = 101
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char = ;code = 32
char = W;code = 87
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = v;code = 118
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = g;code = 103
char = a;code = 97
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char = e;code = 101
char = d;code = 100
char = ;code = 32
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char = h;code = 104
char = e;code = 101
char = ;code = 32
char = e;code = 101
char = f;code = 102
char = f;code = 102
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = s;code = 115
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char = ;code = 32
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char = e;code = 101
char = w;code = 119
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 = o;code = 111
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = r;code = 114
char = o;code = 111
char = w;code = 119
char = t;code = 116
char = h;code = 104
char = ,;code = 44
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = p;code = 112
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char = a;code = 97
char = g;code = 103
char = e;code = 101
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
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char = f;code = 102
char = i;code = 105
char = n;code = 110
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = f;code = 102
char = l;code = 108
char = u;code = 117
char = o;code = 111
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = c;code = 99
char = e;code = 101
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = i;code = 105
char = s;code = 115
char = o;code = 111
char = t;code = 116
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char = i;code = 105
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = e;code = 101
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char = c;code = 99
char = o;code = 111
char = n;code = 110
char = j;code = 106
char = u;code = 117
char = g;code = 103
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = p;code = 112
char = o;code = 111
char = o;code = 111
char = p;code = 112
char = o;code = 111
char = l;code = 108
char = y;code = 121
char = s;code = 115
char = a;code = 97
char = c;code = 99
char = c;code = 99
char = h;code = 104
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = F;code = 70
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = -;code = 45
char = L;code = 76
char = P;code = 80
char = S;code = 83
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = g;code = 103
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = s;code = 115
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = F;code = 70
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = -;code = 45
char = z;code = 122
char = y;code = 121
char = m;code = 109
char = o;code = 111
char = s;code = 115
char = a;code = 97
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = s;code = 115
char = c;code = 99
char = a;code = 97
char = v;code = 118
char = e;code = 101
char = n;code = 110
char = g;code = 103
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = f;code = 102
char = f;code = 102
char = i;code = 105
char = n;code = 110
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = O;code = 79
char = H;code = 72
char = (;code = 40
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = R;code = 82
char = O;code = 79
char = O;code = 79
char = *;code = 42
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = O;code = 79
char = (;code = 40
char = 2;code = 50
char = );code = 41
char = (;code = 40
char = -;code = 45
char = );code = 41
char = *;code = 42
char = ,;code = 44
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = d;code = 100
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 = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = f;code = 102
char = l;code = 108
char = u;code = 117
char = e;code = 101
char = n;code = 110
char = c;code = 99
char = e;code = 101
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 = i;code = 105
char = n;code = 110
char = f;code = 102
char = l;code = 108
char = a;code = 97
char = m;code = 109
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = [;code = 91
char = n;code = 110
char = i;code = 105
char = t;code = 116
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = N;code = 78
char = O;code = 79
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = u;code = 117
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = n;code = 110
char = e;code = 101
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = s;code = 115
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = -;code = 45
char = a;code = 97
char = l;code = 108
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = ;code = 32
char = (;code = 40
char = T;code = 84
char = N;code = 78
char = F;code = 70
char = -;code = 45
char = a;code = 97
char = l;code = 108
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = s;code = 115
char = t;code = 116
char = a;code = 97
char = g;code = 103
char = l;code = 108
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = E;code = 69
char = -;code = 45
char = 2;code = 50
char = ;code = 32
char = (;code = 40
char = P;code = 80
char = G;code = 71
char = E;code = 69
char = -;code = 45
char = 2;code = 50
char = );code = 41
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 = x;code = 120
char = y;code = 121
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = s;code = 115
char = e;code = 101
char = -;code = 45
char = 2;code = 50
char = ;code = 32
char = (;code = 40
char = C;code = 67
char = O;code = 79
char = X;code = 88
char = -;code = 45
char = 2;code = 50
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 5;code = 53
char = -;code = 45
char = l;code = 108
char = i;code = 105
char = p;code = 112
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = a;code = 97
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = 5;code = 53
char = -;code = 45
char = L;code = 76
char = O;code = 79
char = );code = 41
char = ];code = 93
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = L;code = 76
char = P;code = 80
char = S;code = 83
char = -;code = 45
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = m;code = 109
char = u;code = 117
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = m;code = 109
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = h;code = 104
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = i;code = 105
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = a;code = 97
char = l;code = 108
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 = 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 = s;code = 115
char = ;code = 32
char = 2;code = 50
char = b;code = 98
char = ,;code = 44
char = ;code = 32
char = 3;code = 51
char = b;code = 98
char = ,;code = 44
char = ;code = 32
char = 5;code = 53
char = a;code = 97
char = ,;code = 44
char = ;code = 32
char = 7;code = 55
char = b;code = 98
char = ,;code = 44
char = ;code = 32
char = 9;code = 57
char = a;code = 97
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = 9;code = 57
char = b;code = 98
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = c;code = 99
char = o;code = 111
char = g;code = 103
char = n;code = 110
char = i;code = 105
char = z;code = 122
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = i;code = 105
char = s;code = 115
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = m;code = 109
char = u;code = 117
char = l;code = 108
char = t;code = 116
char = i;code = 105
char = -;code = 45
char = p;code = 112
char = o;code = 111
char = t;code = 116
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = -;code = 45
char = i;code = 105
char = n;code = 110
char = f;code = 102
char = l;code = 108
char = a;code = 97
char = m;code = 109
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = s;code = 115
char = .;code = 46
char = <;code = 60
char = b;code = 98
char = r;code = 114
char = /;code = 47
char = >;code = 62
result sql = The reaction of 2-acetyl-5,6,7,8-tetrahydronaphthalene 1 with some aldehydes was conducted in the presence of ethyl cyanoacetate and ammonium acetate, yielded the cyanopyridones 2a-c, which react with phosphorous pentasulphide to afford the corresponding thioxopyridine derivatives 3a-c, respectively. Compounds 2a,b were converted to 2-chloropyridine derivatives 4a,b by heating with phosphorous oxychloride and phosphorous pentachloride, which were fused with hydrazine hydrate and benzyl amine to afford the corresponding pyrazolopyridine 5a,b and cyanopyridine derivatives 6a,b respectively. Compounds 2a,b also afforded 3-cyanopyridinyl oxy acetic acid ethyl ester 7a,b by reaction with ethyl bromoacetate in dry acetone in the presence of anhydrous potassium carbonate, which upon condensation with hydrazine hydrate gave the corresponding acid hydrazide 8a,b and with benzyl amine gave the corresponding acetamide 9a,b. We investigated the effect of those new compounds on the macrophage growth, macrophage binding affinity to fluorescein isothiocyanate-conjugated bacterial lipoopolysaccharide (FITC-LPS), phagocytosis of FITC-zymosan, and radical scavenging affinity against OH(), ROO*, and O(2)(-)*, in addition to their influence of the inflammatory mediators [nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), prostaglandin E-2 (PGE-2), cycloxygenase-2 (COX-2), and 5-lipoxygenase (5-LO)] in LPS-stimulated macrophages. The findings revealed that the derivatives 2b, 3b, 5a, 7b, 9a and 9b can be recognized as promising multi-potent anti-inflammatory agents.
Publication: Eur J Med Chem 2009 Nov ;44(11)::4547-56. :doi: 10.1016/j.ejmech.2009.06.023.
Publication Date: 2009 Nov
Study Author(s): Hamdy, Nehal A;Gamal-Eldeen, Amira M;
Institution: Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt. [email protected]
Shortcut link to this study:
Publication Date: 2009 Nov
Study Author(s): Hamdy, Nehal A;Gamal-Eldeen, Amira M;
Institution: Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt. [email protected]
Shortcut link to this study:
The reaction of 2-acetyl-5,6,7,8-tetrahydronaphthalene 1 with some aldehydes was conducted in the presence of ethyl cyanoacetate and ammonium acetate, yielded the cyanopyridones 2a-c, which react with phosphorous pentasulphide to afford the corresponding thioxopyridine derivatives 3a-c, respectively. Compounds 2a,b were converted to 2-chloropyridine derivatives 4a,b by heating with phosphorous oxychloride and phosphorous pentachloride, which were fused with hydrazine hydrate and benzyl amine to afford the corresponding pyrazolopyridine 5a,b and cyanopyridine derivatives 6a,b respectively. Compounds 2a,b also afforded 3-cyanopyridinyl oxy acetic acid ethyl ester 7a,b by reaction with ethyl bromoacetate in dry acetone in the presence of anhydrous potassium carbonate, which upon condensation with hydrazine hydrate gave the corresponding acid hydrazide 8a,b and with benzyl amine gave the corresponding acetamide 9a,b. We investigated the effect of those new compounds on the macrophage growth, macrophage binding affinity to fluorescein isothiocyanate-conjugated bacterial lipoopolysaccharide (FITC-LPS), phagocytosis of FITC-zymosan, and radical scavenging affinity against OH(), ROO*, and O(2)(-)*, in addition to their influence of the inflammatory mediators [nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), prostaglandin E-2 (PGE-2), cycloxygenase-2 (COX-2), and 5-lipoxygenase (5-LO)] in LPS-stimulated macrophages. The findings revealed that the derivatives 2b, 3b, 5a, 7b, 9a and 9b can be recognized as promising multi-potent anti-inflammatory agents.
PMID: 19616348
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