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Paper Details

Synthesis and antifungal activity of some new fluorinated 1-[2-hydroxyethyl] -3-ethoxycarbonyl-5 oxadiazolyl/triazolyl/ pyrrolylaminocarbonylmethoxy-2- methylbenz [g] indoles

Anil KumarMittal1, Dharamveer Singh2, SatyaprakashTripathi*3.

Journal Title:Journal of Chemical, Biological and physical sciences
Abstract


The exclusive formation of 1-[2- aryl]-3-ethoxycarbonyl-7-halo-2-methylbenz [g] indol-5- yloxyacetic acid hydrazides (5a-c) from 1-[2-aryl]-3-ethoxycarbonyl 5- hydroxy-7-halo-2- methylbenz [g] indoles (3a-c) revealed the chemo selectivity of the C5 - ester over C3-ester towards nucleophillic attack of hydrazine hydrate. This monocarbohydrazide (5a-c) is reacted separately with CS2/KOH , acetonyl acetone and isothiocyanates to secure the desired 1-[2-aryl]-3- ethoxycarbonyl-5-(5-mercapto-1,3,4-oxadiazol-2-yl) methoxy-7-halo-2-methylbenz [g] indoles (8ac), 1-[2-aryl]-3-ethoxycarbonyl-5-(2,5-dimethylpyrrol-1-yl) aminocarbonylmethoxy-7- halo-2- methylbenz [g] indoles (9a-c) and 1-[2-aryl]-3-ethoxycarbonyl-5-(aryl1substituted thiosemicarbazinocarbonyl) methoxy-7-halo -2- methylbenz [g] indoles (6a-i). These thiosemicarbazides (6a-i) are reacted with 4% NaOH to produce the 1-[2-aryl] 5-(4-aryl1subsituted- 5-mercapto-1, 2, 4-triazol-3-yl) methoxy-7-halo -2- methylbenz [g] indole-3-carboxylic acid (7a-i).Antifungal activity has been compared with Dithane M-45, a commercial fungicide for their fungi toxic action against Phytopthora infestans and Collectotricum falcatum, and the results correlated with their features.

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