Synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino] propanoic acid and evaluation of anti-microbial activity

被引：9
作者：
Pund, Amit A. [1 ]
Saboo, Shweta S. [2 ]
Sonawane, Gajanan M. [3 ]
Dukale, Amol C. [4 ]
Magare, Baban K. [1 ]
机构：
[1] Shivaji Arts Commerce & Sci Coll, Dept Chem, UG PG & Res Ctr, Aurangabad, Maharashtra, India
[2] Govt Coll Pharm, Aurangabad, Maharashtra, India
[3] Rajarshi Shahu Coll Pharm, Buldhana, Maharashtra, India
[4] Swami Muktanand Coll Sci Yeola, Yeola, Maharashtra, India
来源：
SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 24期
关键词：
Anti-microbial; carbonyldiimidazole; evaluation; pyridine-2-carboxylic acid hydrazide; 1; 3; 4-thiadiazole; SCHIFF-BASE; SPECTRAL CHARACTERIZATION; ANTIOXIDANT ACTIVITIES; CYTOTOXIC ACTIVITIES; 1,3,4-THIADIAZOLE; ANTIBACTERIAL; 1,3,4-OXADIAZOLE; 1,2,4-TRIAZOLE; ANTIFUNGAL; DESIGN;
D O I：
10.1080/00397911.2020.1817488
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The new compoundsAP-1toAP-10were synthesized from starting material (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1). The intermediate 2,5-disubstituted-1,3,4-thiadiazole amine (5) was prepared by coupling of (2S)-3-(Benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1) with pyridine-2-carboxylic acid hydrazide (2) in the presence of carbonyldiimidazole (CDI) followed by 1,3,4-thiadiazole ring formation via diacylhydrazines derivative (3) and deprotection with shorter reaction time and excellent yield. The structures of new compounds were confirmed by spectral analysis. The series of new synthesized compoundsAP-1toAP-10were evaluated for their anti-microbial activitiesin vitroand compoundsAP-1,AP-3,AP-4, andAP-10showed strong activities against all tested microorganisms.
引用
收藏
页码：3854 / 3864
页数：11
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