Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole
Construction, molecular docking, antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole
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DOI：
10.1016/j.jscs.2021.101360
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发表时间：
2021-10-16
影响因子：
5.6
通讯作者：
Zafar, Rehman
中科院分区：
文献类型：
--
作者：
Al-Khaldi, Alanoud;Ghoneim, Amira Atef;Zafar, Rehman
本论文提出了一种3位带有杂环取代基的取代吲哚的合成方法。杂环取代基吲哚的合成路线从3-乙酰基吲哚核开始。 3-乙酰基吲哚1与苯肼、水合肼、氨基硫脲等酰肼化合物反应，分别生成3-(1-(2苯基亚肼基)乙基)-1H-吲哚2、3-(1-亚肼基乙基)-1H-吲哚6、缩氨基硫脲10。噻吩-2-甲醛、靛红和3-乙酰吲哚与3-(1-亚肼基乙基)-1H-吲哚6反应。同样，3-(1-(2-苯基亚肼基)乙基)-1H-吲哚2与巯基乙酸、甘氨酸和苯甲醛反应。缩氨基硫脲10与乙酐、哌啶、浓盐酸、噻吩二甲醛顺利反应，得到相应的杂环。 3-乙酰吲哚1与对硝基苯胺等胺类化合物反应生成席夫碱15，席夫碱15与巯基乙酸反应生成化合物16。3-乙酰吲哚1与乙二胺反应生成双亚胺吲哚17。对接研究报告显示，新化合物具有良好的抗菌活性。体外筛选的合成化合物的抗菌活性显示出对所选微生物的显着抑制作用。此外，还研究了一些新设计的化合物的抗氧化活性。新合成的化合物的结构通过光谱数据（IR、1HNMR、13C NMR 和质谱）进行检查。 (c) 2021 年作者。由 Elsevier B.V. 代表沙特国王大学出版。这是一篇遵循 CC BY-NC-ND 许可证 (http://creativecommons.org/licenses/by-nc-nd/4.0/) 的开放获取文章。
This dissertation presents a method for the synthesis of substituted indoles bearing heterocyclic substituent in the 3-position. The route for the synthesis of the heterocyclic substituents indoles starts from the 3-acetyl indole nucleus. The reaction of 3-acetyl indole 1 with hydrazide compounds such as phenylhydrazine, hydrazine hydrate, and thio-semicarbazide, yields 3-(1-(2phenylhydrazono) ethyl)-1H-indole 2, 3-(1-hydrazonoethyl)-1H-indole 6, and thiosemicarbazone 10, respectively. Thiophene-2-carboxaldeyde, isatine and 3-acetyl indole reacted with 3-(1Hydrazonoethyl)-1H-indole 6. In the same way, 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2 reacted with thioglycollic acid, glycine and benzaldehyde. Thiosemicarbazone 10 reacted smoothly with acetic anhydride, piperidine, concentration of hydrochloric acid and thiophene-2carboxaldeyde to provide the corresponding heterocycles. The reaction of 3-acetyl indole 1 with amine compounds such as p-nitroaniline formed Schiff base 15, which reacted with thioglycollic acid to give compound 16. 3-Acetyl indole 1 reacted with ethylene diamine to afford bis imine indole 17. The reports of the docking study revealed that the new compounds exhibit good antibacterial activity. The synthesized compounds screened in vitro for their antibacterial activity revealed remarkable inhibitory effects on the selected microorganisms. Besides, the antioxidant activity of some newly designed compounds has been investigated. The structures of the newly synthesized compounds are examined by spectral data (IR, 1HNMR, 13C NMR and mass spectra). (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).