Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides
Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides
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DOI：
10.3109/14756366.2016.1160077
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发表时间：
2016-01-01
影响因子：
5.6
通讯作者：
Supuran, Claudiu T.
中科院分区：
文献类型：
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作者：
Gul, Halise Inci;Tugrak, Mehtap;Supuran, Claudiu T.
以2-（4-取代亚苄基）-2，3-二氢-1H-茚-1-酮（1-6）和4-肼基苯磺酰胺为原料，合成了一系列新的4-（3-（4-取代苯基）-3a，4-二氢-3H-茚并[1，2-c]吡唑-2-基）苯磺酰胺（7- 1,2）。取代的苯甲醛，通过引入2-或4-取代基如氟、羟基、甲氧基或3，4，5-三甲氧基部分来制备关键中间体。测试化合物的细胞毒性、肿瘤特异性和作为碳酸酐酶（CA，EC 4.2.1.1）抑制剂的潜力。3，4，5-三甲氧基和4-羟基衍生物显示出有趣的细胞毒性活性，这可能是进一步的抗肿瘤活性研究的关键，而这些磺胺类药物中的一些强烈抑制人类（h）细胞溶质异构体hCA I和II。
A series of new 4-(3-(4-substitutedphenyl)-3a, 4-dihydro-3H-indeno[1,2-c] pyrazol-2-yl) benzenesulfonamides (7-12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1-6) and 4-hydrazinobenzenesulfonamide. The substituted benzaldehydes from which the key intermediate was prepared by introducing 2- or 4-substituents such as fluorine, hydroxy, methoxy, or the 3,4,5-trimethoxy moieties. The compounds were tested for their cytotoxicity, tumor-specificity and potential as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The 3,4,5-trimethoxy and the 4-hydroxy derivatives showed interesting cytotoxic activities, which may be crucial for further anti-tumor activity studies, whereas some of these sulfonamides strongly inhibited both human (h) cytosolic isoforms hCA I and II.