Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents

IF 1.4 4区 化学 Q3 CHEMISTRY, ORGANIC Chemistry of Heterocyclic Compounds Pub Date : 2024-04-08 DOI:10.1007/s10593-024-03298-z
Chenghao Tang, Jiali Shao, Chou Si, Xiumei Yang, Xiuhong Hu, Pei Li, Xiang Wang
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Abstract

A series of twenty one novel compounds derived from indole-3-acetic acid, the structure of which includes 1,3,4-thiadiazole, thioether, and amide moieties were designed, synthesized, and evaluated for their in vitro antibacterial activity against three bacterial strains. The bioassay results showed that among the synthesized compounds, N-{5-[(2-fluorobenzyl)sulfanyl]-1,3,4-thiadiazol-2-yl}-3-(1H-indol-3-yl)-propanamide demonstrated the best inhibition rate against Pseudomonas syringae pv. actinidiae and N-{5-[(4-chlorobenzyl)sulfanyl]-1,3,4-thiadiazol-2-yl}-3-(1H-indol-3-yl)propanamide possessed the best inhibition rate against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri, in all cases superior to that of bactericides thiodiazole copper and bismerthiazol.

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发现含有 1,3,4-噻二唑硫醚和酰胺分子的吲哚-3-乙酸衍生物作为新型抗菌剂
本研究设计、合成了一系列源自吲哚-3-乙酸的 21 种新型化合物,其结构包括 1,3,4-噻二唑、硫醚和酰胺分子,并评估了它们对三种细菌菌株的体外抗菌活性。生物测定结果表明,在合成的化合物中,N-{5-[(2-氟苄基)硫基]-1,3,4-噻二唑-2-基}-3-(1H-吲哚-3-基)-丙酰胺对绿脓杆菌 pv.而 N-{5-[(4-氯苄基)硫基]-1,3,4-噻二唑-2-基}-3-(1H-吲哚-3-基)丙酰胺对黄单胞菌(Xanthomonas oryzae pv. oryzae)和黄单胞菌(Xanthomonas axonopodis pv. citri)的抑制率最佳,在所有情况下都优于杀菌剂硫二唑铜和双噻唑。
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来源期刊
CiteScore
2.90
自引率
13.30%
发文量
98
审稿时长
1 months
期刊介绍: The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemo­ra­tives dedicated to prominent heterocyclic chemists.
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