New dioxazole derivatives: Synthesis and effects on the growth of Entamoeba histolytica and Giardia intestinalis

被引:12
作者
Irfan, Iram [1 ]
Sawangjaroen, Nongyao [2 ,3 ]
Bhat, Abdul R. [1 ]
Azam, Amir [1 ]
机构
[1] Jamia Millia Islamia, Dept Chem, New Delhi 110025, India
[2] Prince Songkla Univ, Fac Sci, Nat Prod Res Ctr, Hat Yai 90112, Thailand
[3] Prince Songkla Univ, Fac Sci, Dept Microbiol, Hat Yai 90112, Thailand
关键词
Dioxazoles derivatives; G; intestinalis; E; histolytica; Toxicity studies; METRONIDAZOLE; CHEMOTHERAPY; AMEBIASIS; PROTOZOA;
D O I
10.1016/j.ejmech.2009.12.051
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Cyclization of oxime with different aldehydes and ketones under basic condition led to the formation of new dioxazole derivatives and the structure was elucidated by spectral data. The effects of diaoxazoles on the inhibition of growth of Entamoeba histolytica and Giardia intestinalis in vitro have been determined, and selected compounds further investigated for their toxicity. SAR showed that the compounds with 5-nitrothiophene group at the 3-postion of the diaoxazole ring were more active than those with the p-toluene group at the same position. It is interesting to note that the compounds found active against E. histolytica were not found active against G. intestinalis. Toxicity studies showed that the compound 8 and 9 were non-toxic against Vero cell line ATCC CCL-81. (c) 2010 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:1648 / 1653
页数:6
相关论文
共 27 条
[1]   Successful treatment of metronidazole- and albendazole-resistant giardiasis with nitazoxanide in a patient with acquired immunodeficiency syndrome [J].
Abboud, P ;
Lemée, V ;
Gargala, G ;
Brasseur, P ;
Ballet, JJ ;
Borsa-Lebas, F ;
Caron, F ;
Favennec, L .
CLINICAL INFECTIOUS DISEASES, 2001, 32 (12) :1792-1794
[2]  
[Anonymous], 1997, Wkly Epidemiol Rec, V72, P97
[3]   Formation of azole-resistant Candida albicans by mutation of sterol 14-demethylase P450 [J].
Asai, K ;
Tsuchimori, N ;
Okonogi, K ;
Perfect, JR ;
Gotoh, O ;
Yoshida, Y .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1999, 43 (05) :1163-1169
[4]  
BHAT AR, 2008, EUR J MED CHEM 0304
[5]   SEROEPIDEMIOLOGY OF AMEBIASIS IN MEXICO [J].
CABALLEROSALCEDO, A ;
VIVEROSROGEL, M ;
SALVATIERRA, B ;
TAPIACONYER, R ;
SEPULVEDAAMOR, J ;
GUTIERREZ, G ;
ORTIZORTIZ, L .
AMERICAN JOURNAL OF TROPICAL MEDICINE AND HYGIENE, 1994, 50 (04) :412-419
[6]   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
[7]   Reproductive and cytogenetic toxicity of metronidazole in male mice [J].
El-Nahas, AF ;
El-Ashmawy, IM .
BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY, 2004, 94 (05) :226-231
[8]   BRUCEANTIN, A POTENT AMEBICIDE FROM A PLANT, BRUCEA-ANTIDYSENTERICA [J].
GILLIN, FD ;
REINER, DS ;
SUFFNESS, M .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1982, 22 (02) :342-345
[9]   Muscarine, imidazole, oxazole, and thiazole alkaloids [J].
Jin, Z .
NATURAL PRODUCT REPORTS, 2003, 20 (06) :584-605
[10]   Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation [J].
Kaffy, Julia ;
Pontikis, Renee ;
Carrez, Daniele ;
Croisy, Alain ;
Monneret, Claude ;
Florent, Jean-Claude .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (12) :4067-4077