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
收藏
页码：114 / 121
页数：8
相关论文
共 50 条
  • [41] 3-(4-Fluorophenyl)-1-(1-(4-fluorophenyl)-3,3,3-trifluoroprop-1-en-1-yl)-5-fluoro-1H-pyrazole
    Paveliev, Stanislav A.
    Ustyuzhanin, Alexander O.
    Krylov, Igor B.
    Terent'ev, Alexander O.
    MOLBANK, 2023, 2023 (02)
  • [42] Synthesis, spectroscopic studies and biological applications of organotin(IV) derivatives of 3-[N-(4-nitrophenyl)-amido]propenoic acid and 3-[N-(4-Nitrophenyl)-amido]propanoic acid
    Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
    Bull. Korean Chem. Soc., 2006, 1 (44-52):
  • [43] 3-[(3S)-3-Ethyl-1-methylazepan-3-yl]-phenyl N-(4-fluorophenyl)carbamate
    Sun, Jian
    Xie, Qiong
    Qiu, Zhui-Bai
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1822 - U756
  • [44] Synthesis and crystal structure of 1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
    Patil, P. S.
    Shettigar, V.
    Dharmaprakash, S. M.
    Naveen, S.
    Sridhar, M. A.
    Prasad, J. Shashidhara
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2006, 461 : 123 - 130
  • [45] Synthesis and Antifungal Activity of N-(Substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide Derivatives
    Wu, Zhibing
    Hu, Deyu
    Kuang, Jiqing
    Cai, Hua
    Wu, Shixi
    Xue, Wei
    MOLECULES, 2012, 17 (12): : 14205 - 14218
  • [46] 5-Benzoyl-N,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxamide
    He, Long
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2281 - U3149
  • [47] Synthesis and biological evaluation of 3-(4-fluorophenyl)-1H-pyrazole derivatives as androgen receptor antagonists
    Guo, Guangzhu
    Liu, Jianzhen
    Wang, Guanjie
    Zhang, Daoguang
    Lu, Jinjie
    Zhao, Guisen
    ANTI-CANCER DRUGS, 2016, 27 (04) : 278 - 285
  • [48] Crystal structure of 5-[4-(dimethylamino)phenyl]-3-(4-methylphenyl)-4,5dihydro-1H-pyrazole-1-carbaldehyde
    Adam, Farook
    Samshuddin, Seranthimata
    Ameram, Nadiah
    Subramaya
    Samartha, Laxminarayana
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O1031 - U1147
  • [49] 3-(4-Fluorophenyl)-2-(4-methoxyphenoxy)-4-oxo-5-phenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile
    Zeng, Guo-Ping
    Yan, Shi-Rong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1680 - U1250
  • [50] Synthesis of 3-[(4-Nitrophenyl)thio]-Substituted 4-Methylene-1-pyrrolines from N-Propargylic β-Enaminones
    Korkmaz, Esra
    Zora, Metin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07): : 4937 - 4950
12345