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NOVEL MURRAYANINE BASED PYRAZOLE ANALOGS AS EMERGING ANTI-FUNGAL CANDIDATES: DESIGN, SYNTHESIS, CHARACTERIZATION, AND IN VITRO EVALUATION

Abstract

A new series of murrayanine based pyrazole derivatives were synthesized from murrayanine- chalcone derivatives using hydrazine hydrate as the reagent. The fabricated derivatives were characterized using modern sophisticated analytical techniques like IR, 1H NMR, 13C NMR and Mass spectral data. The in-vitro antifungal activity of newly synthesized compounds (3a-h) was evaluated against various pathogenic fungal strains; Candida albicans (C. albicans, MTCC 227), Aspergillus niger (A. niger, MTCC 277), Aspergillus flavus (A. flavus, MTCC 418), Cryptococcus neoformans (C. neoformans, MTCC 6333) and Chrysosporium tropicum (C. tropicum, MTCC 2821). The compound 3-(5-(3,5-bis(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol- 3-yl)-1-methoxy-9H-carbazole (3g) expressed the highest activity among the other derivatives. The analogs (3a) and (3c) presented the lowest activity among all the fabricated products. The presence of two CF3 groups was found to enhance the activity owing to the lipophilic nature. The ortho position was detected to be less privileged as compared to both meta and para substituted compounds. In this study, the compound with two meta substitutions was found to be better fungicidal than para substituted analogs. It can be concluded that the study opened new avenues in future where further novel anti-fungal compounds may be designed based on this template.
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