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

被引：2

作者：

Ahsan, Mohamed J. ^{[1
]}

Kumawat, Bhawani S. ^{[1
]}

Kumawat, Sonu ^{[1
]}

Sharma, Piush ^{[1
]}

Bakht, Mohammad A. ^{[2
]}

Hassan, Mohd Z. ^{[3
]}

Hussain, Afzal ^{[4
]}

Saraswat, Pankaj ^{[5
]}

Khalilullah, Habibullah ^{[6
]}

机构：

[1] Maharishi Arvind Coll Pharm, Dept Pharmaceut Chem, Jaipur 302039, Rajasthan, India

[2] Prince Sattam Bin Abdulaziz Univ, Coll Sci & Humanities, Dept Chem, POB 11323, Al Kharj, Saudi Arabia

[3] King Khalid Univ, Coll Pharm, Dept Pharmaceut Chem, Abha 62529, Saudi Arabia

[4] Birla Inst Sci & Technol, Dept Pharmaceut Sci & Technol, Ranchi 835215, Jharkhand, India

[5] Alwar Pharm Coll, Dept Pharmaceut Chem, Alwar 301030, Rajasthan, India

[6] Qassim Univ, Unaizah Coll Pharm, Dept Pharmaceut Chem, Al Qassim 51911, Saudi Arabia

来源：

SYNOPEN | 2018年 / 2卷 / 02期

关键词：

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

D O I：

10.1055/s-0036-1591980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-fluoroace-tophenone. 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 GI(50) <0.1 and 45.8 mu M 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.

引用

页码：114 / 121

页数：8

共 50 条

[11] 5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-4,5-dihydro-1H-pyrazole
Jasril, Jasril
Zamri, Adel
Ikhtiarudin, Ihsan
Teruna, Hilwan Y.
MOLBANK, 2016, (02)
[12] 4-(4-Fluorophenyl)-1-(4-nitrophenyl)3-(pyridin-4-yl)-1H-pyrazol-5-amine
Abu Thaher, Bassam
Koch, Pierre
Schollmeyer, Dieter
Laufer, Stefan
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O633 - U1597
[13] 5-(Anthracen-9-yl)-3-(4-nitrophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
Dong, Bao-Li
Wang, Ming-Liang
Li, Yong-Hua
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2786 - U2317
[14] 3,5-Bis(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
Jasinski, Jerry P.
Guild, Curtis J.
Samshuddin, S.
Narayana, B.
Yathirajan, H. S.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1948 - U607
[15] Synthesis, antitubercular evaluation and 3D-QSAR study of N-phenyl-3-(4-fluorophenyl)-4-substituted pyrazole derivatives
Khunt, R. C.
Khedkar, V. M.
Chawda, R. S.
Chauhan, N. A.
Parikh, A. R.
Coutinho, E. C.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) : 666 - 678
[16] 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde
Baktir, Zeliha
Akkurt, Mehmet
Samshuddin, S.
Narayana, B.
Yathirajan, H. S.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1292 - U1756
[17] 4,5-dihydro-3-methyl-5-(4-methyl-phenyl)-1H-pyrazole-1-carboxamide
Kettmann, V
Svetlík, J
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2003, 59 : O419 - O421
[18] N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl] acetamide
Kavitha, H. D.
Marganakop, Sheetal B.
Kamble, Ravindra R.
Roopashree, K. R.
Devarajegowda, H. C.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O701 - +
[19] Two tautomers in the same crystal: 3-(4-fluorophenyl)-1H-pyrazole and 5-(4-fluorophenyl)-1H-pyrazole
Yamuna, Thammarse S.
Kaur, Manpreet
Jasinski, Jerry P.
Anderson, Brian J.
Yathirajan, H. S.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O949 - +
[20] 1-[3-(4-Fluorophenyl)-5-phenyl-4,5dihydro-1H-pyrazol-1-yl]ethanone
Fun, Hoong-Kun
Ooi, Chin Wei
Sapnakumari, M.
Narayana, B.
Sarojini, B. K.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2634 - +

← 1 2 3 4 5 →