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CC BY-ND-NC 4.0 · SynOpen 2018; 02(02): 0114-0121
DOI: 10.1055/s-0036-1591980
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Synthesis and Cytotoxic Evaluation of 3-(4-Fluorophenyl)-4,5-dihydro-5-(3,4,5-trimethoxy/4-nitrophenyl)-N-(substituted-phenyl)pyrazole-1-carboxamide Analogues

Mohamed J. Ahsan  *
a   Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, India   Email: jawedpharma@gmail.com
,
Bhawani S. Kumawat
a   Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, India   Email: jawedpharma@gmail.com
,
Sonu Kumawat
a   Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, India   Email: jawedpharma@gmail.com
,
Piush Sharma
a   Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan 302 039, India   Email: jawedpharma@gmail.com
,
Mohammad A. Bakht
b   Department of Chemistry, College of Science & Humanities, Prince Sattam Bin Abdulaziz University, P.O. Box 11323, Saudi Arabia
,
Mohd Z. Hassan
c   Department of Pharmaceutical Chemistry, College of Pharmacy, King Khalid University, Abha 62529, Saudi Arabia
,
Afzal Hussain
d   Department of Pharmaceutical Science & Technology, Birla Institute of Science & Technology, Mesra, Ranchi, Jharkhand 835 215, India
,
Pankaj Saraswat
e   Department of Pharmaceutical Chemistry, Alwar Pharmacy College, Alwar, Rajasthan 301 030, India
,
Habibullah Khalilullah
f   Department of Pharmaceutical Chemistry, Unaizah College of Pharmacy, Qassim University, Al-Qassim 51911, Kingdom of Saudi Arabia
› Author Affiliations
Further Information

Publication History

Received: 24 January 2018

Accepted after revision: 14 March 2018

Publication Date:
23 April 2018 (online)

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Abstract

A novel series of 3-(4-fluorophenyl)-4,5-dihydro-5-(3,4,5-trimethoxy/4-nitro phenyl)-N-(substituted-phenyl)pyrazole-1-carboxamide analogues 4a–n was synthesized in two steps from 4-fluoroacetophenone. The pyrazoline analogues were evaluated for cytotoxicity against two breast cancer cell lines (MCF-7 and MBA-MD-231) by the sulforhodamine B (SRB) assay. N-(4-Chlorophenyl)-3-(4-fluorophenyl)-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI50 <0.1 and 45.8 μM against the cancer cell lines, MCF-7 and MDA-MB-231, respectively. The anticancer activity of 4b was found to be comparable to that of the standard drug adriamycin (GI50 <0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.

Key words

anticancer agents - breast cancer cell lines - MCF-7 - MDA-MB-231 - SRB assay - pyrazolines
 

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