Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride
Synthesis of biologically active N-methyl derivatives of amidines and cyclized five-membered products of amidines with oxalyl chloride
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DOI：
10.1016/j.ejmech.2007.10.005
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发表时间：
2008-12-01
影响因子：
6.7
通讯作者：
Kumar, Ashok
中科院分区：
文献类型：
--
作者：
Sondhi, Sham M.;Dinodia, Monica;Kumar, Ashok
以N-甲基异烟肼(1a-I)为原料，在三乙胺存在下与碘甲烷反应，合成了一系列N-甲基异烟肼(2a-f)、N-甲基吡嗪-2-甲基肼(2g-I)衍生物。二氢咪唑基苯磺酰胺衍生物(1a-I)与酰化剂草酰氯反应，合成了五元缩合二氢咪唑苯磺酰胺衍生物(3a-I)。所有化合物，即2a-I和3a-I，都是通过结晶提纯的。所有合成的化合物的结构都得到了正确的红外光谱、核磁共振氢谱、质谱图和分析数据的支持。采用角叉菜胶足肿胀实验进行抗炎活性评价，化合物2e、3a和3d具有较好的抗炎活性(50 mg/kgP.O.活性分别为44%、31%和37%)。采用醋酸扭体法进行镇痛活性评价，化合物2a和3f在100 mg/kg P.O.时的镇痛活性分别为75%，而化合物3a和3D在50 mg/kg P.O.化合物3a和3d具有良好的抗炎和镇痛活性。(C)2007年爱思唯尔·马森公司。版权所有。
A series of substituted N-methylisonicotinamidine (2a-f), N-methylpyrazine-2-carboxamidine (2g-i) derivatives were synthesized by reaction of amidine derivatives (1a-i) with methyl iodide in presence of triethylamine. Five-membered condensed dihydroimidazolylbenzene-sulfonamide derivatives (3a-i) were obtained by the reaction of amidine derivatives (1a-i) with acylating agent oxalyl chloride. All the compounds, i.e. 2a-i and 3a-i were purified by crystallization. Structures of all the synthesized compounds are supported by correct IR, H-1 NMR, mass spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenan-induced paw oedema assay and compounds 2e, 3a and 3d exhibited good anti-inflammatory activity (44%, 31% and 37% activity at 50 mg/kg p.o., respectively). Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 2a and 3f gave 75% activity each at 100 mg/kg p.o.; on the other hand compounds 3a and 3d exhibited 60% analgesic activity each at 50 mg/kg p.o. Compounds 3a and 3d exhibited good anti-inflammatory and analgesic activities. (C) 2007 Elsevier Masson SAS. All rights reserved.