Synthesis, anticancer activity and molecular docking study of (E)-4-(3,4Dichlorophenyl)-2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one derivatives

被引:0
作者
Sadanandam, Kudikala [1 ]
Pinnoju, Prasad [1 ]
Manasa, S. K. [1 ]
Sarasija, Madderla [1 ]
机构
[1] Satavahana Univ, Dept Chem, Karimnagar, Telangana, India
关键词
Claisen-Schmidt condensation; Sertralone; pyrazole aldehyde; cytotoxic activity; molecular docking study; ANTIFUNGAL ACTIVITY; DESIGN; ANTIBACTERIAL; PYRAZOLES;
D O I
暂无
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A novel series of (E)-4-(3,4-Dichlorophenyl)-2-((1,3-diphenyl- 1H-pyrazol-4-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one derivatives were synthesized by Claisen-Schmidt condensation of 4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one and 1,3-diphenyl-1H-pyrazole-4-carbaldehyde. All the synthesized targets were evaluated for their cytotoxicity against a panel of three cancer cells (SiHa, MDA-MB-231 and PANC-1). Among the tested compounds, many of them exhibited significant anticancer activity, the compound 8a was found to be the most promising analogue in this series with IC50 values of 1.56 mu M on breast cancer cells.
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页数:5
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共 26 条
[1]   Non-acidic 1,3,4-trisubstituted-pyrazole derivatives as lonazolac analogs with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile [J].
Abdellatif, Khaled R. A. ;
Fadaly, Wael A. A. ;
Elshaier, Yaseen A. M. M. ;
Ali, Waleed A. M. ;
Kamel, Gehan M. .
BIOORGANIC CHEMISTRY, 2018, 77 :568-578
[2]   SYNTHESIS AND ANTIFUNGAL ACTIVITY OF SOME 3-BENZYLIDENECHROMAN-4-ONES, 3-BENZYLIDENETHIOCHROMAN-4-ONES AND 2-BENZYLIDENE-1-TETRALONES [J].
ALNAKIB, T ;
BEZJAK, V ;
MEEGAN, MJ ;
CHANDY, R .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1990, 25 (05) :455-462
[3]   Synthesis and Antimicrobial Evaluation of Novel Pyrazole-Annulated Oxygen-Containing Macrocycles [J].
Ashok, Dongamanti ;
Devulapally, Mohan Gandhi ;
Gundu, Srinivas ;
Aamate, Vikas Kumar ;
Chintalapally, Shivakanth .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (08) :609-614
[4]   Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents [J].
Bandgar, Babasaheb P. ;
Gawande, Shrikant S. ;
Bodade, Ragini G. ;
Gawande, Nalini M. ;
Khobragade, Chandrahasya N. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (24) :8168-8173
[5]   Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents [J].
Bekhit, AA ;
Abdel-Aziem, T .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) :1935-1945
[6]   Recent Developments in the Chemistry of Pyrazoles [J].
Brown, Andrew W. .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 126, 2018, 126 :55-107
[7]   Synthesis of functionalized tetrasubstituted pyrazolyl heterocycles - A review [J].
Dadiboyena, Sureshbabu ;
Nefzi, Adel .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5258-5275
[8]   Design, synthesis, and in vitro antiproliferative and kinase inhibitory effects of pyrimidinylpyrazole derivatives terminating with arylsulfonamido or cyclic sulfamide substituents [J].
El-Din, Mahmoud M. Gamal ;
El-Gamal, Mohammed I. ;
Abdel-Maksoud, Mohammed S. ;
Yoo, Kyung Ho ;
Baek, Daejin ;
Choi, Jungseung ;
Lee, Huiseong ;
Oh, Chang-Hyun .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 :111-122
[9]   Preparation of 3,5-Disubstituted Pyrazoles and Isoxazoles from Terminal Alkynes, Aldehydes, Hydrazines, and Hydroxylamine [J].
Harigae, Ryo ;
Moriyama, Katsuhiko ;
Togo, Hideo .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (05) :2049-2058
[10]   Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives [J].
Hassan, Seham Y. .
MOLECULES, 2013, 18 (03) :2683-2711