Target-oriented synthesis of antiparasitic 2-hetaryl substituted quinolines based on imino Diels-Alder reactions

被引：32
作者：
Kouznetsov, Vladimir V. [1 ]
Vargas Mendez, Leonor Y.
Milena Leal, Sandra
Mora Cruz, Uriel
Andres Coronado, Carlos
Melendez Gomez, Carlos M.
Romero Bohorquez, Arnold R.
Escobar Rivero, Patricia
机构：
[1] Univ Ind Santander, Escuela Quim, CIBIMOL, Lab Quim Organ & Biomol, Bucaramanga 678 AA, Colombia
[2] Univ Ind Santander, Escuela Med, Dept Ciencias Basicas, CINTROP,Ctr Invest Enfermedades Trop, Bucaramanga 678 AA, Colombia
来源：
LETTERS IN DRUG DESIGN & DISCOVERY | 2007年 / 4卷 / 04期
关键词：
antiparasitic activities; target-oriented synthesis; 2-hetarylquinolines; Leishmania chagasi; trypanosoma cruzi; drug discovery;
D O I：
10.2174/157018007784620031
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Target-oriented synthesis of new substituted 2-hetarylquinolines 6-19 and their in vitro activity against endemic parasites such as Leishmania chagasi and Trypanosoma cruzi are reported. In addition, their cytotoxicities for mammalian Vero cells and THP-1 macrophages cells are assessed. These studies showed that between the new (tetrahydro)quinolines series tested in these assays, the 4-methyl-8-isopropyl-2-(3-pyridinyl)quinoline 15 exhibits the best in vitro response against both live forms of T. cruzi and L. chagasi parasites and displays no cytotoxic activity on mammalian cells.
引用
收藏
页码：293 / 296
页数：4
相关论文
共 17 条
[1]   Chemotherapy of trypanosomiases and leishmaniasis [J].
Croft, SL ;
Barrett, MP ;
Urbina, JA .
TRENDS IN PARASITOLOGY, 2005, 21 (11) :508-512
[2]   Phase 2 trial of WR6026, an orally administered 8-aminoquinoline, in the treatment of visceral leishmaniasis caused by Leishmania chagasi [J].
Dietze, R ;
Carvalho, SFG ;
Valli, LC ;
Berman, J ;
Brewer, T ;
Milhous, W ;
Sanchez, J ;
Schuster, B ;
Grogl, M .
AMERICAN JOURNAL OF TROPICAL MEDICINE AND HYGIENE, 2001, 65 (06) :685-689
[3]   Sensitivities of Leishmania species to hexadecylphosphocholine (miltefosine), ET-18-OCH3 (edelfosine) and amphotericin B [J].
Escobar, P ;
Matu, S ;
Marques, C ;
Croft, SL .
ACTA TROPICA, 2002, 81 (02) :151-157
[4]   Synthesis and biological evaluation of substituted quinolines:: Potential treatment of protozoal and retroviral co-infections [J].
Fakhfakh, MA ;
Fournet, A ;
Prina, E ;
Mouscadet, JF ;
Franck, X ;
Hocquemiller, R ;
Figadère, B .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :5013-5023
[5]   Biological evaluation of substituted quinolines [J].
Franck, X ;
Fournet, A ;
Prina, E ;
Mahieux, R ;
Hocquemiller, R ;
Figadère, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3635-3638
[6]   Transformation of Schiff bases derived from α-naphthaldehyde.: Synthesis, spectral data and biological activity of new-3-aryl-2-(α-naphtyl)-4-thiazolidinones and N-aryl-N-[1-(α-naphthyl)but-3-enyl]amines [J].
Kouznetsov, V ;
Rodríguez, W ;
Stashenko, E ;
Ochoa, C ;
Vega, C ;
Rolón, M ;
Pereira, DM ;
Escario, JA ;
Barrio, AG .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (06) :995-999
[7]   An efficient synthesis of new C-2 aryl substituted quinolines based on three component imino Diels-Alder reaction [J].
Kouznetsov, VV ;
Bohórquez, ARR ;
Saavedra, LA ;
Medina, RF .
MOLECULAR DIVERSITY, 2006, 10 (01) :29-37
[8]   4-Aryl(benzyl)amino-4-heteroarylbut-1-enes as building blocks in heterocyclic synthesis.: 4.: Synthesis of 4,6-dimethyl-5-nitro(amino)2-pyridylquinolines and their antiparasitic activities [J].
Kouznetsov, VV ;
Méndez, LYV ;
Tibaduiza, B ;
Ochoa, C ;
Pereira, DM ;
Ruiz, JJN ;
Portillo, CF ;
Serrano, SM ;
Barrio, AG ;
Bahsas, A ;
Amaro-Luis, J .
ARCHIV DER PHARMAZIE, 2004, 337 (03) :127-132
[9]  
KOUZNETSOV VV, 2006, IN PRESS J HETEROCYC, V43
[10]   CHEMISTRY OF IMINES [J].
LAYER, RW .
CHEMICAL REVIEWS, 1963, 63 (05) :489-+
12