Synthesis 1-Acyl-3-(2′-aminophenyl) thioureas as Anti-Intestinal Nematode Prodrugs

被引：30

作者：

Duan, Li-Ping ^{[1
]}

Xue, Jia ^{[1
]}

Xu, Li-Li ^{[1
]}

Zhang, Hao-Bing ^{[1
]}

机构：

[1] Chinese Ctr Dis Control & Prevent, Natl Inst Parasit Dis, Shanghai 200025, Peoples R China

来源：

MOLECULES | 2010年 / 15卷 / 10期

关键词：

acyl; thiourea; deparasitization; Nippostrongylus brazilliensis; INCREASED WATER-SOLUBILITY; DERIVATIVES; MEBENDAZOLE;

D O I：

10.3390/molecules15106941

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of 1-acyl-3-(2'-aminophenyl) thiourea derivatives were designed and synthesized. The structures of all the newly synthesized compounds were identified by IR, elemental analysis, H-1-NMR and C-13-NMR. Their anti-intestinal nematode activities against Nippostrongylus brazilliensis were evaluated in rats by an oral route. Among these compounds, at concentrations of 10 mg/kg of rat, compound (1-(2'-furanyl)acyl-3- (2'-aminophenyl) thiourea) (5h) produced the highest activity with 89.4% deparasitization. The present work suggests that 1-acyl-3-(2'-aminophenyl) thiourea derivatives may become useful lead compounds for anti-intestinal nematode treatment.

引用

页码：6941 / 6947

页数：7

共 18 条

[1] Synthesis and in vitro antiprotozoal activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazone derivatives [J].

Bharti, N ;

Husain, K ;

Garza, MTG ;

Cruz-Vega, DE ;

Castro-Garza, J ;

Mata-Cardenas, BD ;

Naqvi, F ;

Azam, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (23) :3475-3478

[2]

CAVIER R, 1973, CHEMOTHERAPY HELMINT, V1, P215

[3] Flubendazole in cystic echinococcosis therapy: Pharmaco-parasitological evaluation in mice [J].

Ceballos, Laura ;

Elissondo, Maria ;

Sanchez Bruni, Sergio ;

Denegri, Guillermo ;

Alvarez, Luis ;

Lanusse, Carlos .

PARASITOLOGY INTERNATIONAL, 2009, 58 (04) :354-358

[4] The detection of anthelmintic resistance in nematodes of veterinary importance [J].

Coles, GC ;

Jackson, F ;

Pomroy, WE ;

Prichard, RK ;

von Samson-Himmelstjerna, G ;

Silvestre, A ;

Taylor, MA ;

Vercruysse, J .

VETERINARY PARASITOLOGY, 2006, 136 (3-4) :167-185

[5] Flubendazole interferes with a wide spectrum of cell homeostatic mechanisms in Echinococcus granulosus protoscoleces [J].

Cumino, Andrea C. ;

Celina Elissondo, Maria ;

Denegri, Guillermo M. .

PARASITOLOGY INTERNATIONAL, 2009, 58 (03) :270-277

[6] 4-AMINO-3-(3'-METHOXYCARBONYL-2'-THIOUREIDO) BENZOPHENONE, A PRODRUG OF MEBENDAZOLE [J].

DAWSON, M ;

WATSON, TR .

EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, 1983, 8 (04) :329-334

[7] The changing landscape of antiparasitic drug discovery for veterinary medicine [J].

Geary, TG ;

Conder, GA ;

Bishop, B .

TRENDS IN PARASITOLOGY, 2004, 20 (10) :449-455

[8] Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi [J].

Greenbaum, DC ;

Mackey, Z ;

Hansell, E ;

Doyle, P ;

Gut, J ;

Caffrey, CR ;

Lehrman, J ;

Rosenthal, PJ ;

McKerrow, JH ;

Chibale, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3212-3219

[9] Synthesis and hydrolytic stability studies of albendazole carrier prodrugs [J].

Hernández-Luis, F ;

Hernández-Campos, A ;

Yépez-Mulia, L ;

Cedillo, R ;

Castillo, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (11) :1359-1362

[10] Paralytic ileus and subsequent death caused by enteric parasite, Strongyloides papillosus, in Mongolian gerbils [J].

Kobayashi, Ikuo ;

Kajisa, Makoto ;

Farid, Ayman Samir ;

Yamanaka, Atsushi ;

Horii, Yoichiro .

VETERINARY PARASITOLOGY, 2009, 162 (1-2) :100-105

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