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Open AccessProceedings

Synthesis of Novel and Potential Antimicrobial, Antioxidant and Anticancer Chalcones and Dihydropyrazoles Bearing Isoxazole Scaffold

1
Vignan Pharmacy College, Vadlamudi 522213, Andhra Pradesh, India
2
ASN Pharmacy College, Tenali 522201, Andhra Pradesh, India
*
Author to whom correspondence should be addressed.
Presented at the 23rd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2019; Available online: https://ecsoc-23.sciforum.net/.
Proceedings 2019, 41(1), 16; https://doi.org/10.3390/ecsoc-23-06476
Published: 14 January 2020
A series of isoxazole based (E)-1-(isoxazole-5-yl)-3-(substituted phenyl)-prop-2-en-1-ones (chalcones, 3a-3o) and 3-(isoxazol-5-yl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide (dihydropyrazoles, 4a-4o) were synthesized, characterized and evaluated for their antimicrobial, antioxidant and anticancer properties. Chalcones exhibited excellent antibacterial and antioxidant activities whereas the dihydropyrazoles shown superior antifungal and anticancer activities. The compound 3l containing 3,4,5-trimethoxy phenyl ring showed the potent antibacterial activity (MIC = 1 µg/mL) as well as the antioxidant activity (IC50 = 5 µg/mL) whereas the dihydropyrazole, 4o (MIC = 0.5 µg/mL) bearing the 2-chloro-3,4-dimethoxyphenyl was the potent antifungal compound identified. The dihydropyrazoles 4n and 4h possessing 2-fluoro-3,4-dimethoxyphenyl and 3,4-dimethoxyphenyl substituents exhibited potent anticancer activity against prostate cancer cell line (DU-145) with MIC 2 and 4 µg/mL respectively. The structure activity relationships had shown that there is a marked influence of both electron withdrawing halogens and electron releasing methoxyl groups on the above biological activities. All the compounds were evaluated for toxicity on normal human cell lines (LO2) and found to be non-toxic. These studies could help to synthesize, explore and identify new isoxazole containing leads for antimicrobial, antioxidant and anticancer properties.
Keywords: isoxazole; chalcones; dihydropyrazole; antibacterial activity; antifungal activity; anticancer activity; structure activity relationships isoxazole; chalcones; dihydropyrazole; antibacterial activity; antifungal activity; anticancer activity; structure activity relationships
MDPI and ACS Style

Shaik, A.; Kishor, P.; Kancharlapalli, V. Synthesis of Novel and Potential Antimicrobial, Antioxidant and Anticancer Chalcones and Dihydropyrazoles Bearing Isoxazole Scaffold. Proceedings 2019, 41, 16.

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