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

The new compounds AP-1 to AP-10 were 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...

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Bibliographic Details
Published in:Synthetic communications 2020-12, Vol.50 (24), p.3854-3864
Main Authors: Pund, Amit A., Saboo, Shweta S., Sonawane, Gajanan M., Dukale, Amol C., Magare, Baban K.
Format: Article
Language:English
Subjects:
1,3,4-thiadiazole
Acids
Anti-microbial
Antiinfectives and antibacterials
Biological activity
carbonyldiimidazole
Carbonyls
Carboxylic acids
evaluation
Microorganisms
Propionic acid
pyridine-2-carboxylic acid hydrazide
Reaction time
Spectrum analysis
Synthesis
Thiadiazoles
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Summary:The new compounds AP-1 to AP-10 were 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 compounds AP-1 to AP-10 were evaluated for their anti-microbial activities in vitro and compounds AP-1, AP-3, AP-4, and AP-10 showed strong activities against all tested microorganisms.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1817488