Synthesis and cytotoxicity of some novel 21E-benzylidene steroidal derivatives

被引:19
作者
Fan, Ning-Juan [1 ]
Bai, Yu-Bin [1 ]
Zhang, Fei-Yu [1 ]
Luo, Bo [1 ]
Tang, Jiang-Jiang [1 ]
Zhang, Qiang-Zhe [2 ]
Gao, Jin-Ming [1 ]
机构
[1] Northwest A&F Univ, Coll Sci, Shaanxi Engn Ctr Bioresource Chem & Sustainable U, Yangling 712100, Shaanxi, Peoples R China
[2] Nankai Univ, Ctr Chem Genom & Med Technol, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Progesterone; Aldol reaction; Benzylidene steroidal derivatives; Cytotoxicity; ANTICANCER ACTIVITIES; CHALCONE DERIVATIVES; ANTIFUNGAL; ANALOGS;
D O I
10.1016/j.steroids.2013.04.016
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 series of novel derivatives of 21E-benzylidene-pregn-1,4-diene-3,20-dione 7a-g and 21E-benzylidene-4-chloro-pregn-1,4-diene-3,20-dione 8a-g was synthesized from the commercially available progesterone. These title compounds were evaluated for their cytotoxic activity against brine shrimp (Artemia salina) and murine Lewis lung carcinoma cells (LLC). It was found that compounds 7a-g exhibited stronger activities than 8a-g against the brine shrimps, and some of the tested compounds possessed weak inhibition of LLC cells. (C) 2013 Elsevier Inc. All rights reserved.
引用
收藏
页码:874 / 879
页数:6
相关论文
共 31 条
[1]   ANTICANCER AND ANTIOXIDANT ACTIVITY OF SYNTHETIC CHALCONES AND RELATED-COMPOUNDS [J].
ANTO, RJ ;
SUKUMARAN, K ;
KUTTAN, G ;
RAO, MNA ;
SUBBARAJU, V ;
KUTTAN, R .
CANCER LETTERS, 1995, 97 (01) :33-37
[2]   Synthesis and antimicrobial studies of chalconyl pregnenolones [J].
Banday, Abid H. ;
Zargar, M. Iqbal ;
Ganaie, Bashir A. .
STEROIDS, 2011, 76 (12) :1358-1362
[3]   Synthesis of chalcone analogues with increased antileishmanial activity [J].
Boeck, P ;
Falcao, CAB ;
Leal, PC ;
Yunes, RA ;
Cechinel, V ;
Torres-Santos, EC ;
Rossi-Bergmann, B .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1538-1545
[4]   OXIDATION OF NATURAL TARGETS BY DIOXIRANES - OXYFUNCTIONALIZATION OF STEROIDS [J].
BOVICELLI, P ;
LUPATTELLI, P ;
MINCIONE, E ;
PRENCIPE, T ;
CURCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2182-2184
[5]  
Cabeza M, 1999, CHEM PHARM BULL, V47, P1232
[6]   Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate [J].
Carvalho, Joao F. S. ;
Cruz Silva, M. Manuel ;
Sa e Melo, M. Luisa .
TETRAHEDRON, 2009, 65 (14) :2773-2781
[7]  
Chattopadhaya R, 2004, ARZNEIMITTELFORSCH, V54, P551
[8]   Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata [J].
Cheenpracha, S ;
Karalai, C ;
Ponglimanont, C ;
Subhadhirasakul, S ;
Tewtrakul, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (06) :1710-1714
[9]   A practical Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature [J].
Chen, Kaixiong ;
Liu, Chang ;
Deng, Le ;
Xu, Guangyu .
STEROIDS, 2010, 75 (07) :513-516
[10]   Synthesis and evaluation of new antimalarial phenylurenyl chalcone derivatives [J].
Domínguez, JN ;
León, C ;
Rodrigues, J ;
de Domínguez, NG ;
Gut, J ;
Rosenthal, PJ .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) :3654-3658