Synthesis and biological evaluation of some 6-substituted purines

被引:34
作者
Braga, Fernanda Gambogi
Coimbra, Elaine Soares
Matos, Magnum de Oliveira
Lino Carmo, Arturene Maria
Cancio, Marisa Damato
da Silva, Adilson David
机构
[1] Univ Fed Juiz Fora, Inst Ciencias Exatas, Dept Quim, BR-36036900 Juiz de Fora, MG, Brazil
[2] Univ Fed Juiz Fora, Inst Ciencias Biol, Dept parasitol Microbiol & Imunol, BR-36036900 Juiz de Fora, MG, Brazil
关键词
6-substituted purines; antileishmanial activity;
D O I
10.1016/j.ejmech.2006.10.014
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We report herein the synthesis and the in vitro antileishmanial evaluation of a series of 6-substituted purines. The most active compounds against Leishmania amazonensis promastigotes were 6-(3'-chloropropylthio)purine 2 (D.A. Benson, I. Karsch-Mizrachi, D.J. Lipman, J. Ostell, B.A. Rapp, D.L. Wheeler, Genbank., Nucleic Acids Res. 28 (2000) 15-18; E.V. Aleksandrova, P.M.I.E. Valashek, J. Med. Pharm. Chem. 35 (2001) 172-173), 6-(3'-(thioethylamine)propylthio)purine 5, 6-(alpha-aceticacidthio)purine-7 and 6-(6'-deoxy-1'-O-methyl-beta-D-ribofuranose)purine 14 with an IC50 = 50, 50, 39 and 29 mu M, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:530 / 537
页数:8
相关论文
共 22 条
[1]   Purine nucleobase transport in amastigotes of Leishmania mexicana:: Involvement in allopurinol uptake [J].
Al-Salabi, MI ;
de Koning, HP .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (09) :3682-3689
[2]   A Leishmania major nucleobase transporter responsible for allopurinol uptake is a functional homolog of the Trypanosoma brucei H2 transporter [J].
Al-Salabi, MI ;
Wallace, LJM ;
De Koning, HP .
MOLECULAR PHARMACOLOGY, 2003, 63 (04) :814-820
[3]  
ALEKSANDROVA EV, 2001, J MED PHARM CHEM, V35, P172
[4]   GenBank [J].
Benson, DA ;
Karsch-Mizrachi, I ;
Lipman, DJ ;
Ostell, J ;
Rapp, BA ;
Wheeler, DL .
NUCLEIC ACIDS RESEARCH, 2000, 28 (01) :15-18
[5]   A conditional mutant deficient in hypoxanthine-guanine phosphoribosyltransferase and xanthine phosphoribosyltransferase validates the purine salvage pathway of Leishmania donovani [J].
Boitz, Jan M. ;
Ullman, Buddy .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (23) :16084-16089
[6]   Plant natural products with leishmanicidal activity [J].
Chan-Bacab, MJ ;
Peña-Rodríguez, LM .
NATURAL PRODUCT REPORTS, 2001, 18 (06) :674-688
[7]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF METHYL-D-GLUCOPYRANOSIDE DERIVATIVES OF MERCAPTOPURINE AND MERCAPTOPYRIMIDINE [J].
DASILVA, AD ;
MACHADO, AS ;
TEMPETE, C ;
ROBERTGERO, M .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (02) :149-152
[8]   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
[9]   Synthesis and in vitro leishmanicidal activity of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-5-substituted-1,3,4-thiadiazole derivatives [J].
Foroumadi, A ;
Emami, S ;
Pournourmohammadi, S ;
Kharazmi, A ;
Shafiee, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) :1346-1350
[10]   Novel methods for the encapsulation of meglumine antimoniate into liposomes [J].
Frézard, F ;
Michalick, MSM ;
Soares, CF ;
Demicheli, C .
BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH, 2000, 33 (07) :841-846