Remarkable anti-breast cancer activity of ferrocene tagged multi-functionalized 1,4-dihydropyrimidines

被引：35
作者：
Jadhav, Jagannath [1 ]
Juvekar, Aarti [2 ]
Kurane, Rajanikant [1 ]
Khanapure, Sharanabasappa [1 ]
Salunkhe, Rajashri [1 ]
Rashinkar, Gajanan [1 ]
机构：
[1] Shivaji Univ, Dept Chem, Kolhapur 416004, MS, India
[2] Tata Mem Hosp, Adv Ctr Treatment Res & Educ Canc, Navi Mumbai 410210, MS, India
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 65卷
关键词：
Ferrrocene; 1,4-Dihydropyrimidines; Ferrocenyl chalcones; Amidines; Anti breast cancer activity; ANTICANCER ACTIVITY; ASYMMETRIC CATALYSIS; DERIVATIVES; LIGANDS; DIHYDROPYRIMIDINES; ELECTROCHEMISTRY; ANTAGONISTS; INHIBITION; DENDRIMERS; CHALCONES;
D O I：
10.1016/j.ejmech.2013.04.021
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A novel series of ferrocene tagged multi-functionalized 1,4-dihydropyrimidines is synthesized by base catalyzed cyclocondensation between ferrocenyl chalcones and amidines. The structures of synthesized compounds were established on the basis of H-1 NMR, C-13 NMR, FTIR spectroscopy as well as by mass spectrometry. The compounds were evaluated for in vitro anticancer activity. The most active compounds from the series displayed GI(50) value equal to doxorubicin against the strain of human breast cancer cell line MDA-MB-435. (C) 2013 Elsevier Masson SAS. All rights reserved.
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收藏
页码：232 / 239
页数：8
相关论文
共 50 条
[1]   Functionality of amidines and amidrazones [J].
Aly, Ashraf A. ;
Nour-El-Din, Ahmed M. .
ARKIVOC, 2008, :153-194
[2]   Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].
Arrayas, Ramon Gomez ;
Adrio, Javier ;
Carretero, Juan Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715
[3]   Synthesis of amidine and bis amidine derivatives and their evaluation for anti-inflammatory and anticancer activity [J].
Arya, Surbhi ;
Kumar, Nikhil ;
Roy, Partha ;
Sondhi, S. M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 59 :7-14
[4]  
Astruc D., 1995, Electron Transfer and Radical Processes in Transition-Metal Chemistry
[5]   The syntheses and catalytic applications of unsymmetrical ferrocene ligands [J].
Atkinson, RCJ ;
Gibson, VC ;
Long, NJ .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :313-328
[6]   DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].
CHO, H ;
UEDA, M ;
SHIMA, K ;
MIZUNO, A ;
HAYASHIMATSU, M ;
OHNAKA, Y ;
TAKEUCHI, Y ;
HAMAGUCHI, M ;
AISAKA, K ;
HIDAKA, T ;
KAWAI, M ;
TAKEDA, M ;
ISHIHARA, T ;
FUNAHASHI, K ;
SATOH, F ;
MORITA, M ;
NOGUCHI, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406
[7]   Asymmetric catalysis with chiral ferrocene ligands [J].
Dai, LX ;
Tu, T ;
You, SL ;
Deng, WP ;
Hou, XL .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (09) :659-667
[8]   Biological evaluation of twenty-eight ferrocenyl tetrasubstituted olefins: Cancer cell growth inhibition, ROS production and hemolytic activity [J].
de Oliveira, Alane Cabral ;
Hillard, Elizabeth A. ;
Pigeon, Pascal ;
Rocha, Danilo Damasceno ;
Rodrigues, Felipe A. R. ;
Montenegro, Raquel C. ;
Costa-Lotufo, Leticia V. ;
Goulart, Marilia O. F. ;
Jaouen, Gerard .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :3778-3787
[9]   Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids [J].
Deres, K ;
Schröder, CH ;
Paessens, A ;
Goldmann, S ;
Hacker, HJ ;
Weber, O ;
Krämer, T ;
Niewöhner, U ;
Pleiss, U ;
Stoltefuss, J ;
Graef, E ;
Koletzki, D ;
Masantschek, RNA ;
Reimann, A ;
Jaeger, R ;
Gross, R ;
Beckermann, B ;
Schlemmer, KH ;
Haebich, D ;
Rübsamen-Waigmann, H .
SCIENCE, 2003, 299 (5608) :893-896
[10]   Click Syntheses of 1,2,3-Triazolylbiferrocenyl Dendrimers and the Selective Roles of the Inner and Outer Ferrocenyl Groups in the Redox Recognition of ATP2- and Pd2+ [J].
Djeda, Rodrigue ;
Rapakousiou, Amalia ;
Liang, Liyuan ;
Guidolin, Nicola ;
Ruiz, Jaime ;
Astruc, Didier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) :8152-8156
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