新型吡唑啉衍生物的合成、构效关系及抗结核活性
Synthesis, structural activity relationship and anti-tubercular activity of novel pyrazoline derivatives.
作者信息
Ali Mohamed Ashraf, Shaharyar Mohammad, Siddiqui Anees Ahamed
机构信息
Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi 110062, India.
出版信息
Eur J Med Chem. 2007 Feb;42(2):268-75. doi: 10.1016/j.ejmech.2006.08.004. Epub 2006 Sep 26.
In the present investigation, a series of 5-(-4-(substituted) phenyl)-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-toluidino methane thione and 5-(substituted) phenyl-3-(4-hydroxy-3-methylphenyl)-4,5-dihydro-1H-1-pyrazolyl-2-methoxyanilino methane thione were synthesized by the reaction between hydrazine hydrate and chalcones (3a-k) followed by condensation with appropriate aryl isothiocyanate which yielded N-substituted pyrazoline derivatives. Newly synthesized compounds were tested for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the synthesized compounds, compound anilino-3-(4-hydroxy-3-methylphenyl)-5-(2,6-dichlorophenyl)-4,5-dihydro-1H-1-pyrazolylmethanethione (6i) was found to be more active agent against M. tuberculosis H37Rv with minimum inhibitory concentration of 0.0034 microM.
在本研究中，通过水合肼与查耳酮（3a - k）反应，随后与适当的芳基异硫氰酸酯缩合，合成了一系列5 -（- 4 -（取代）苯基）- 3 -（4 - 羟基 - 3 - 甲基苯基）- 4,5 - 二氢 - 1H - 1 - 吡唑基 - 2 - 甲苯胺基甲硫酮和5 -（取代）苯基 - 3 -（4 - 羟基 - 3 - 甲基苯基）- 4,5 - 二氢 - 1H - 1 - 吡唑基 - 2 - 甲氧基苯胺基甲硫酮，得到了N - 取代的吡唑啉衍生物。使用BACTEC 460放射测量系统对新合成的化合物进行了针对结核分枝杆菌H37Rv的体外抗结核活性测试。在合成的化合物中，发现化合物苯胺基 - 3 -（4 - 羟基 - 3 - 甲基苯基）- 5 -（2,6 - 二氯苯基）- 4,5 - 二氢 - 1H - 1 - 吡唑基甲硫酮（6i）是对结核分枝杆菌H37Rv更具活性的药剂，最低抑菌浓度为0.0034 microM。
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