Mulwad Vinata V, Langi Bhushan P, Chaskar Atul C
Department of Chemistry, The Institute of Science, 15 Madam Cama Road, Mumbai 400 032, India.
Acta Pol Pharm. 2011 Jan-Feb;68(1):39-47.
6-Aminocoumarin on treatment with oxalyl chloride gives coumarinyl-6-isocynate (1a-c) which on treatment with glycine gives 1H-3-[2'-oxo-2'H-benzopyran-6'-yl]-5-imidazolidine-2, 4-dione (2a-c). (2a-c) when refluxed with o-chlorobenzaldehyde, m-hydroxybenzaldehyde, 3,4-dimethoxybenzaldehyde and 3-nitrobenzaldehyde separately gives 1H-5-(2"-chlorobenzylidene)-3-(2'-oxo-2'H-benzopyran-6'-yl) imidazolidine-2,4-dione (3a-c), 1H-5-(3"-hydroxybenzylidene)-3-(2'-oxo-2'H-benzopyran-6'-yl) imidazolidine-2,4-dione (4a-c), 1H-5-(3",4"-dimethoxybenzylidene)-3-(2'-oxo-2'H-benzopyran-6'-yl) imidazolidine-2,4-dione (5a-c) and 1H-5-(3"-nitrobenzylidene)-3-(2'-oxo-2'H-benzopyran-6'-yl) imidazolidine-2,4-dione (6a-c), respectively. 3-(2"-Chlorophenyl)-3a,4-dihydro-6-(2'-oxo-2'H-benzopyran-6'-yl) imidazo[4,5-c]isoxazol-5-one 7a-c is obtained from (3a-c) and hydroxylamine hydrochloride while 2,3a,4-trihydro-3-(3"-hydroxyphenyl)-6-(2'-oxo-2'H-benzopyran-6'-yl) imidazo[4,5-c]pyrazol-5-one (8a-c) obtained by reaction of (4a-c) with hydrazine hydrate. Compound (5a-c) on treatment with urea gives 5,7-dihydro-2-hydroxy-6-(3",4"-dimethoxyphenyl)-9-(2'-oxo-2'H-benzopyran-6'-yl) purin-8-one (9a-c) and compound (6a-c) on treatment with thiourea gives 5,7-dihydro-2-mercapto-6-(3"-nitrophenyl)-9-(2'-oxo-2'H-benzopyran-6'-yl)purin-8-one (10a-c). The structures of the compounds have been established on the basis of spectral analytical data. All the compounds have been screened for their antimicrobial activities against three bacterial strains S. aureus, S. typhi and E. coli. Compounds 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b and 10b with the presence of methyl groups at C7' and C8' of coumarin moiety were found to be more active than others.
6-氨基香豆素与草酰氯反应生成香豆素基-6-异氰酸酯（1a - c），其与甘氨酸反应生成1H - 3 - [2'-氧代-2'H - 苯并吡喃-6'-基]-5-咪唑烷-2,4-二酮（2a - c）。（2a - c）分别与邻氯苯甲醛、间羟基苯甲醛、3,4-二甲氧基苯甲醛和3-硝基苯甲醛回流反应，分别生成1H - 5 -（2''-氯亚苄基）-3 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑烷-2,4-二酮（3a - c）、1H - 5 -（3''-羟基苯亚甲基）-3 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑烷-2,4-二酮（4a - c）、1H - 5 -（3'',4''-二甲氧基苯亚甲基）-3 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑烷-2,4-二酮（5a - c）和1H - 5 -（3''-硝基苯亚甲基）-3 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑烷-2,4-二酮（6a - c）。3 -（2''-氯苯基）-3a,4-二氢-6 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑并[4,5 - c]异恶唑-5-酮7a - c由（3a - c）与盐酸羟胺反应制得，而2,3a,4-三氢-3 -（3''-羟基苯基）-6 -（2'-氧代-2'H - 苯并吡喃-6'-基）咪唑并[4,5 - c]吡唑-5-酮（8a - c）通过（4a - c）与水合肼反应制得。化合物（5a - c）与尿素反应生成5,7-二氢-2-羟基-6 -（3'',4''-二甲氧基苯基）-9 -（2'-氧代-2'H - 苯并吡喃-6'-基）嘌呤-8-酮（9a - c），化合物（6a - c）与硫脲反应生成5,7-二氢-2-巯基-6 -（3''-硝基苯基）-9 -（2'-氧代-2'H - 苯并吡喃-6'-基）嘌呤-8-酮（10a - c）。这些化合物的结构已根据光谱分析数据确定。所有化合物均针对金黄色葡萄球菌、伤寒沙门氏菌和大肠杆菌这三种细菌菌株进行了抗菌活性筛选。发现香豆素部分的C7'和C8'位存在甲基的化合物2b、3b、4b、5b、6b、7b、8b、9b和10b比其他化合物更具活性。
