Synthesis of 4-aminoquinoline analogues and their platinum(II) complexes as new antileishmanial and antitubercular agents

被引：54

作者：

Carmo, Arturene M. L. ^{[1
]}

Silva, Flavia M. C. ^{[2
]}

Machado, Patricia A. ^{[2
]}

Fontes, Ana P. S. ^{[1
]}

Pavan, Fernando R. ^{[3
]}

Leite, Clarice Q. F. ^{[3
]}

Leite, Sergio R. de A. ^{[4
]}

Coimbra, Elaine S. ^{[2
]}

Da Silva, Adilson D. ^{[1
]}

机构：

[1] Univ Fed Juiz Fora, Dept Quim, ICE, BR-36036900 Juiz de Fora, MG, Brazil

[2] Univ Fed Juiz Fora, Dept Parasitol Microbiol & Imunol, ICB, BR-36036900 Juiz De Fora, MG, Brazil

[3] Univ Estadual Paulista, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP, Brazil

[4] Univ Estadual Paulista, Inst Quim, BR-14801902 Araraquara, SP, Brazil

来源：

BIOMEDICINE & PHARMACOTHERAPY | 2011年 / 65卷 / 03期

基金：

巴西圣保罗研究基金会;

关键词：

4-aminoquinoline analogues; Platinum(II) complexes; Antileishmanial; Antitubercular; Leishmania; Mycobacterium tuberculosis; DRUG DISCOVERY; TUBERCULOSIS; MYCOBACTERIAL; CISPLATIN; RESISTANT;

D O I：

10.1016/j.biopha.2011.01.003

中图分类号：

R-3 [医学研究方法]; R3 [基础医学];

学科分类号：

100103 [病原生物学]; 100218 [急诊医学];

摘要：

A series of 4-amino-7-chloroquinoline derivatives were synthesized by the reaction of 4,7-dichloroquinoline with the corresponding diamine and then with propargyl bromide. In addition, platinum(II) complexes were obtained by reacting some of the organic derivatives with K2PtCl4. Several of the synthesized compounds displayed antituberculosis activities. Compound 3 was 47.5 times more active than amphotericin B against Leishmania chagasi (IC50 = 0.04 mu g/mL). Compounds 5, 6, 7, 9, 10, 11 and 13 presented promising results against Mycobacterium tuberculosis, with MIC values ranging from 12.5 to 15.6 mu g/mL, comparable to the "first and second line'' drugs used to treat tuberculosis. (C) 2011 Elsevier Masson SAS. All rights reserved.

引用

页码：204 / 209

页数：6

共 35 条

[1]

Abel M D, 1996, Drug Des Discov, V14, P31

[2]

Abel M D, 1996, Drug Des Discov, V14, P15

[3]

[Anonymous], GLOB TUB CONTR EP ST

[4]

Mycobacterial persistence: adaptation to a changing environment [J].

Bentrup, KHZ ;

Russell, DG .

TRENDS IN MICROBIOLOGY, 2001, 9 (12) :597-605

[5]

Synthesis and biological evaluation of some 6-substituted purines [J].

Braga, Fernanda Gambogi ;

Coimbra, Elaine Soares ;

Matos, Magnum de Oliveira ;

Lino Carmo, Arturene Maria ;

Cancio, Marisa Damato ;

da Silva, Adilson David .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (04) :530-537

[6]

Chemotherapy of trypanosomiases and leishmaniasis [J].

Croft, SL ;

Barrett, MP ;

Urbina, JA .

TRENDS IN PARASITOLOGY, 2005, 21 (11) :508-512

[7]

Current Treatment and Drug Discovery Against Leishmania spp. and Plasmodium spp.: A Review [J].

Cruz, Angela Kaysel ;

de Toledo, Juliano Simoes ;

Falade, Mofolusho ;

Terrao, Monica Cristina ;

Kamchonwongpaisan, Sumalee ;

Kyle, Dennis E. ;

Uthaipibull, Chairat .

CURRENT DRUG TARGETS, 2009, 10 (03) :178-192

[8]

Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines [J].

De, DYD ;

Krogstad, FM ;

Byers, LD ;

Krogstad, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (25) :4918-4926

[9]

Synthesis, characterization, X-ray structure and in vitro anti mycobacterial and antitumoral activities of Ru(II) phosphine/diimine complexes containing the "SpymMe2" ligand, SpymMe2=4,6-dimethyl-2-mercaptopyrimidine [J].

do Nascimento, Fabio B. ;

Von Poelhsitz, Gustavo ;

Pavan, Fernando R. ;

Sato, Daisy N. ;

Leite, Clarice Q. F. ;

Selistre-de-Araujo, Heloisa S. ;

Ellena, Javier ;

Castellano, Eduardo E. ;

Deflon, Victor M. ;

Batista, Alzir A. .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2008, 102 (09) :1783-1789

[10]

Multidrug-resistant and extensively drug-resistant tuberculosis: The new face of an old disease [J].

Ferguson, Laurie Anne ;

Rhoads, Jacqueline .

JOURNAL OF THE AMERICAN ACADEMY OF NURSE PRACTITIONERS, 2009, 21 (11) :603-609

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