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Chemotherapeutic Agents, XV. Synthesis of 4‐Amino‐3‐pyrazolo‐1,2,4‐triazoles as Antimicrobial Agents
Author(s) -
Ram Vishnu J.,
Mishra Lallan,
Kushwaha D. S.
Publication year - 1989
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19893220202
Subject(s) - chemistry , formic acid , ethanol , acetic anhydride , antimicrobial , acetylacetone , 1,2,4 triazole , acetic acid , bicyclic molecule , guanidine , amino acid , antifungal , organic chemistry , medicinal chemistry , stereochemistry , catalysis , biochemistry , medicine , dermatology
4‐Amino‐3‐hydrazino‐5‐H/methyl‐1,2,4‐triazole dihydrochlorides ( 2a , b ) were obtained by cyclization of triamino‐guanidine‐HCl in formic and acetic acids, respectively. Condensation of 2a with pyrazol‐4‐carbaldehydes in ethanol yielded 3a , b . Cyclocondensation of 2a , b with dimethylmercaptocyanoacrylonitrile, methyl dimethylmercapto‐cyanoacrylate, ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate individually provided 4a – d and 5a – d , respectively. The hydrazones 6a , b were obtained by refluxing 4‐amino‐3‐(5‐amino‐4‐ethoxycarbonyl pyrazol‐1‐yl)‐1,2,4‐triazole ( 5b ) with aryl aldehydes in ethanol. Interaction of 2a with acetylacetone and 2‐ethoxycarbonylcyclopentanone separately yielded 7 and 8 while reaction with 2‐ethoxycarbonylcyclohexanone provided the bicyclic compounds 9a , b . Some of the compounds were screened for antibacterial and antifungal activities but none of them showed any significant activity.