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; Bhawani S. Kumawat; Sonu Kumawat; Piush Sharma; Mohammad A. Bakht; Mohd Z. Hassan; Afzal Hussain; Pankaj Saraswat; Habibullah Khalilullah

doi:10.1055/s-0036-1591980

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, Bhawani S. Kumawat, Sonu Kumawat, Piush Sharma, Mohammad A. Bakht, Mohd Z. Hassan, Afzal Hussain, Pankaj Saraswat, Habibullah Khalilullah

Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

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-1 H -pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI ₅₀<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 (GI ₅₀<0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.

Original language	English
Article number	so-2018-d0007-op
Pages (from-to)	114-121
Number of pages	8
Journal	SynOpen
Volume	2
Issue number	2
DOIs	https://doi.org/10.1055/s-0036-1591980
State	Published - 1 Apr 2018

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1055/s-0036-1591980

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Ahsan, M. J., Kumawat, B. S., Kumawat, S., Sharma, P., Bakht, M. A., Hassan, M. Z., Hussain, A., Saraswat, P., & Khalilullah, H. (2018). 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. SynOpen, 2(2), 114-121. Article so-2018-d0007-op. https://doi.org/10.1055/s-0036-1591980

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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-1 H -pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI 50<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 (GI 50<0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.",

keywords = "anticancer agents, breast cancer cell lines, MCF-7, MDA-MB-231, pyrazolines, SRB assay",

author = "Ahsan, \{Mohamed J.\} and Kumawat, \{Bhawani S.\} and Sonu Kumawat and Piush Sharma and Bakht, \{Mohammad A.\} and Hassan, \{Mohd Z.\} and Afzal Hussain and Pankaj Saraswat and Habibullah Khalilullah",

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doi = "10.1055/s-0036-1591980",

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Ahsan, MJ, Kumawat, BS, Kumawat, S, Sharma, P, Bakht, MA, Hassan, MZ, Hussain, A, Saraswat, P & Khalilullah, H 2018, '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', SynOpen, vol. 2, no. 2, so-2018-d0007-op, pp. 114-121. https://doi.org/10.1055/s-0036-1591980

TY - JOUR

T1 - 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

AU - Ahsan, Mohamed J.

AU - Kumawat, Bhawani S.

AU - Kumawat, Sonu

AU - Sharma, Piush

AU - Bakht, Mohammad A.

AU - Hassan, Mohd Z.

AU - Hussain, Afzal

AU - Saraswat, Pankaj

AU - Khalilullah, Habibullah

PY - 2018/4/1

Y1 - 2018/4/1

N2 - 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-1 H -pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI 50<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 (GI 50<0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.

AB - 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-1 H -pyrazole-1-carboxamide (4b) showed the most promising cytotoxicity among the series, with GI 50<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 (GI 50<0.1) against the MCF-7 cancer cell line. Structure activity relationships (SAR) are also considered.

KW - anticancer agents

KW - breast cancer cell lines

KW - MCF-7

KW - MDA-MB-231

KW - pyrazolines

KW - SRB assay

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DO - 10.1055/s-0036-1591980

M3 - Article

AN - SCOPUS:85101390793

SN - 2509-9396

VL - 2

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EP - 121

JO - SynOpen

JF - SynOpen

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M1 - so-2018-d0007-op

ER -

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

Abstract

Keywords

UN SDGs

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