GdCl3 promoted synthesis of novel pyrimidine fused indazole derivatives and their anticancer activity

被引：24

作者：

Yakaiah, T. ^{[1
]}

Kurumurthy, C. ^{[1
]}

Lingaiah, B. P. V. ^{[1
]}

Narsaiah, B. ^{[1
]}

Pamanji, R. ^{[2
]}

Velatooru, L. R. ^{[2
]}

Rao, J. Venkateswara ^{[2
]}

Gururaj, S. ^{[4
]}

Parthasarathy, T. ^{[4
]}

Sridhar, B. ^{[3
]}

机构：

[1] Indian Inst Chem Technol, Fluoroorgan Div, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Div Toxicol, Hyderabad 500007, Andhra Pradesh, India

[3] Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

[4] Nizam Coll, Dept Chem, Hyderabad 500001, Andhra Pradesh, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2012年 / 21卷 / 12期

关键词：

Indazoles; Aliphatic/aromatic aldehydes; Pyrimidines; Electron rich olefins; Anticancer activity; Rho-kinase (2F2U) protein; GENETIC ALGORITHM;

D O I：

10.1007/s00044-011-9962-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The three component Grieco condensation of indazoles, aliphatic/aromatic aldehydes, and electron rich olefins in the presence of GdCl3 resulted in a novel pyrimidine fused indazoles in single pot under mild conditions. Representative examples were screened for in vitro anti-cancer activity and some of the compounds exhibited promising cytotoxic activity against U937 cell lines in comparable with standard drug etoposide. The data were further compared with structure-based investigations using docking studies with the crystal structure of Rho-kinase (2F2U) protein. The fitness values estimated by genetic algorithm were found to have a good correlation with the experimental inhibitory potencies.

引用

页码：4261 / 4273

页数：13

共 34 条

[1] ISOLATION AND STRUCTURE DETERMINATION OF NIGELLICINE, A NOVEL ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA
ATTAURRAHMAN
MALIK, S
HE, CH
CLARDY, J
[J]. TETRAHEDRON LETTERS, 1985, 26 (23) : 2759 - 2762
[2] NIGELLIDINE - A NEW INDAZOLE ALKALOID FROM THE SEEDS OF NIGELLA-SATIVA
ATTAURRAHMAN
MALIK, S
HASAN, SS
CHOUDHARY, MI
NI, CZ
CLARDY, J
[J]. TETRAHEDRON LETTERS, 1995, 36 (12) : 1993 - 1996
[3] Bose B., 1981, Journal of the Institution of Chemists (India), V53, P273
[4] A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes
Chae, J
Konno, T
Ishihara, T
Yamanaka, H
[J]. CHEMISTRY LETTERS, 2004, 33 (03) : 314 - 315
[5] Chopra RN, 1956, GLOSSARY INDIAN MED, P176
[6] Cole JC, 2005, VIRTUAL SCREENING IN DRUG DISCOVERY, P379
[7] Specific targeted therapy of chronic myelogenous leukemia with imatinib
Deininger, MWN
Druker, BJ
[J]. PHARMACOLOGICAL REVIEWS, 2003, 55 (03) : 401 - 423
[8] Dymock W, 1890, PHARMACOGRAPHIA INDI, V1, P28
[9] Filler R., 1993, STUDIES ORGANIC CHEM, VVol. 48, P362
[10] ROLE REVERSAL IN THE CYCLOCONDENSATION OF CYCLOPENTADIENE WITH HETERODIENOPHILES DERIVED FROM ARYL AMINES AND ALDEHYDES - SYNTHESIS OF NOVEL TETRAHYDROQUINOLINES
GRIECO, PA
BAHSAS, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5855 - 5858

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