Abstract

The synthesis of a series of new 3-phenyl-5-sulfamoyl-N-(7/8/9-(non)substituted-3-oxo-1-thia-4-azaspiro[4.4]non/[4.5]dec-4-yl)-1H-indole-2-carboxamide derivatives and their subsequent testing for antibacterial activity is described in this paper. 4-Sulfamoylbenzenediazonium chloride was synthesized from diazotization of sulfanilamide and sodium nitrite in the presence of HCl and was further allowed to condense with ethyl 2-benzylacetoacetate to produce ethyl 2-benzyl-2-(4-sulfamoylphenyl)hydrazonoacetate. This compound was cyclized to ethyl 5-sulfamoyl-3-phenyl-1H-indole-2-carboxylate employing the Fischer-indole procedure. The reaction of ethyl 5-sulfamoyl-3-phenyl-1H-indole-2-carboxylate with hydrazine hydrate yielded sulfamoyl-3-phenyl-1H-indole-2-carbohydrazide. Through a cyclization process, the spirothiazolidinone derivatives were obtained from the reaction of suitable cyclic ketones with 5-sulfamoyl-3-phenyl-1H-indole-2-carbohydrazide in the presence of thioglycolic acid/thiolactic acid. Structural elucidation of the novel compounds was achieved with the help of UV, IR, ¹H NMR, HSQC, ESI–MS, and as well as elemental analysis. Among all the synthesized compounds tested, four compounds displayed the most promising antibacterial activity. The influence of the substituents and their positions on the antibacterial activity was evaluated.

Graphic abstract

中文翻译：

---

5-氨磺酰基-1 H-吲哚和4-噻唑烷酮基新杂化物的合成及抗菌活性

摘要

一系列新的3-苯基-5-氨磺酰基-N-（7/8 / 9-（非）取代的-3-氧代-1-硫杂-4-氮杂螺[4.4] non / [4.5] dec-的合成本文介绍了4-yl）-1 H-吲哚-2-羧酰胺衍生物及其后续抗菌活性测试。在盐酸存在下，通过磺酰胺和亚硝酸钠的重氮化反应合成4-氨磺酰苯重氮氯化物，然后使其与2-苄基乙酰乙酸乙酯缩合，生成2-苄基-2-（4-氨磺酰基苯基）酰肼基乙酸乙酯。采用Fischer-吲哚方法将该化合物环化为5-氨磺酰基-3-苯基-1 H-吲哚-2-羧酸乙酯。5-氨磺酰基-3-苯基-1 H的反应-吲哚-2-羧酸酯与水合肼生成氨磺酰基-3-苯基-1 H-吲哚-2-碳酰肼。通过环化过程，在硫代乙醇酸/硫代乳酸的存在下，由合适的环状酮与5-氨磺酰基-3-苯基-1 H-吲哚-2-碳酰肼的反应获得了螺噻唑烷酮衍生物。在紫外，红外，¹ H NMR，HSQC，ESI-MS和元素分析的帮助下，对新型化合物进行了结构解析。在所有测试的合成化合物中，四种化合物表现出最有希望的抗菌活性。评价了取代基及其位置对抗菌活性的影响。

图形摘要