Design, synthesis and biological evaluation of 3-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propionic acid hydrazones as antiprotozoal agents

被引：58

作者：

Inam, Afreen ^{[1
]}

Siddiqui, Shadab Miyan ^{[1
]}

Macedo, Tais Soares ^{[2
]}

Magalhaes Moreira, Diogo Rodrigo ^{[2
]}

Lima Leite, Ana Cristina ^{[3
]}

Pereira Soares, Milena Botelho ^{[2
,4
]}

Azam, Amir ^{[1
]}

机构：

[1] Jamia Millia Islamia, Dept Chem, New Delhi 110025, India

[2] Fundacao Oswaldo Cruz, Ctr Pesquisas Goncalo Moniz, BR-40296710 Salvador, BA, Brazil

[3] Univ Fed Pernambuco, Ctr Ciencias Saude, Dept Ciencias Farmaceut, BR-50740520 Recife, PE, Brazil

[4] Hosp Sao Rafael, Ctr Biotecnol & Terapia Celular, BR-41253190 Salvador, BA, Brazil

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 75卷

关键词：

Malaria; Amoebiasis; Aminoquinoline; Piperazinyl derivatives; Acylhydrazone; IN-VITRO; PLASMODIUM-FALCIPARUM; ENTAMOEBA-HISTOLYTICA; ANTIMALARIAL ACTIVITY; ANTIAMEBIC ACTIVITIES; MEDICINAL CHEMISTRY; HYBRID MOLECULES; DRUGS; CHLOROQUINE; MALARIA;

D O I：

10.1016/j.ejmech.2014.01.023

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

N-Acylhydrazones derived from 7-chloro-4-piperazin-1-yl-quinoline were synthesized and biologically evaluated for blood-stage of Plasmodium falciparum and Entamoeba histolytica trophozoites. N-Acylhydrazone F12 was found to inhibit the P. falciparum growth as well as its life cycle with good selectivity, which was achieved by inhibiting hematin formation. Compound F24 showed better IC50 value than the amoebicidal drug metronidazole. (C) 2014 Elsevier Masson SAS. All rights reserved.

引用

页码：67 / 76

页数：10

共 33 条

[1] Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates [J].

Araujo, Nuna C. P. ;

Barton, Victoria ;

Jones, Michael ;

Stocks, Paul A. ;

Ward, Stephen A. ;

Davies, Jill ;

Bray, Patrick G. ;

Shone, Alison E. ;

Cristiano, Maria L. S. ;

O'Neill, Paul M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (07) :2038-2043

[2] Structure-activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities [J].

Bahl, Deepa ;

Athar, Fareeda ;

Pereira Soares, Milena Botelho ;

de Sa, Matheus Santos ;

Magalhaes Moreira, Diogo Rodrigo ;

Srivastava, Rajendra Mohan ;

Lima Leite, Ana Cristina ;

Azam, Amir .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (18) :6857-6864

[3] METHOD FOR TESTING FOR SYNERGY WITH ANY NUMBER OF AGENTS [J].

BERENBAUM, MC .

JOURNAL OF INFECTIOUS DISEASES, 1978, 137 (02) :122-130

[4] Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes [J].

Bispo Junior, Walfrido ;

Alexandre-Moreira, Magna S. ;

Alves, Marina A. ;

Perez-Rebolledo, Anayive ;

Parrilha, Gabrieli L. ;

Castellano, Eduardo E. ;

Piro, Oscar E. ;

Barreiro, Eliezer J. ;

Lima, Lidia Moreira ;

Beraldo, Heloisa .

MOLECULES, 2011, 16 (08) :6902-6915

[5]

Bray PG, 2005, CURR TOP MICROBIOL, V295, P3

[6] A chloroquine-like molecule designed to reverse resistance in Plasmodium falciparum [J].

Burgess, Steven J. ;

Selzer, Audrey ;

Kelly, Jane Xu ;

Smilkstein, Martin J. ;

Riscoe, Michael K. ;

Peyton, David H. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (18) :5623-5625

[7] Antimalarial activity of betulinic acid and derivatives in vitro against Plasmodium falciparum and in vivo in P-berghei-infected mice [J].

de Sa, Matheus Santos ;

Oliveira Costa, Jose Fernando ;

Krettli, Antoniana Ursine ;

Zalis, Mariano Gustavo ;

de Azevedo Maia, Gabriela Lemos ;

Fechine Sette, Ivana Maria ;

Camara, Celso de Amorim ;

Barbosa Filho, Jose Maria ;

Giulietti-Harley, Ana Maria ;

dos Santos, Ricardo Ribeiro ;

Pereira Soares, Milena Botelho .

PARASITOLOGY RESEARCH, 2009, 105 (01) :275-279

[8] NEW MEDIUM FOR AXENIC CULTIVATION OF ENTAMOEBA-HISTOLYTICA AND OTHER ENTAMOEBA [J].

DIAMOND, LS ;

HARLOW, DR ;

CUNNICK, CC .

TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 1978, 72 (04) :431-432

[9] Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain [J].

Diaz, Philippe ;

Xu, Jijun ;

Astruc-Diaz, Fanny ;

Pan, Hao-Min ;

Brown, David L. ;

Naguib, Mohamed .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :4932-4947

[10] Ferrocene conjugates of chloroquine and other antimalarials: the development of ferroquine, a new antimalarial [J].

Dive, Daniel ;

Biot, Christophe .

CHEMMEDCHEM, 2008, 3 (03) :383-391

← 1 2 3 4 →