Synthesis and biological properties of new 5-nitroindazole derivatives

被引：70

作者：

Arán, VJ

Ochoa, C

Boiani, L

Buccino, P

Cerecetto, H

Gerpe, A

González, M

Montero, D

Nogal, JJ

Gómez-Barrio, A

Azqueta, A

de Ceráin, AL

Piro, OE

Castellano, EE

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

[2] UdelaR, Fac Ciencias, Fac Quim, Dept Quim Organ, Montevideo 11400, Uruguay

[3] Univ Complutense, Fac Farm, Dept Parasitol, E-28040 Madrid, Spain

[4] Univ Navarra, Ctr Invest Farmacobiol Aplicada, Navarra 31080, Spain

[5] Natl Univ La Plata, RA-1900 La Plata, Argentina

[6] Inst IFLP, Dept Fis, Fac Ciencias Exactas, RA-1900 La Plata, Argentina

[7] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13560 Sao Carlos, SP, Brazil

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

5-nitroindazoles; synthesis; antiprotozoal and antineoplastic activities; QSAR;

D O I：

10.1016/j.bmc.2005.02.043

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 new 3-alkoxy- or 3-hydroxy-1-[co-(dialkylamino)alkyl]-5-nitroindazoles have been synthesized and their trichomonacidal, antichagasic and antineoplastic properties studied. Five derivatives (5, 6, 8, 9 and 17) showed remarkable trichomonacidal activity against Trichomonas vaginalis at 10 mu g/mL concentration. Three compounds (8, 10, 11) exhibited interesting antichagasic activity and these same compounds moderate antineoplastic activity against TK-10 and HT-29 cell lines. Unspecific cytotoxicity against macrophages has also been evaluated and only compounds 9, 10 and 11 resulted cytotoxic at the higher dose evaluated (100 mu g/mL), loosing cytotoxicity at lower doses. QSAR studies have been carried out. X-ray crystallographic study of compound 8 has been performed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3197 / 3207

页数：11

共 23 条

[1] Design, synthesis and biological evaluation of new potent 5-nitrofuryl derivatives as anti-Trypanosoma cruzi agents.: Studies of trypanothione binding site of trypanothione reductase as target for rational design [J].