Synthesis of some 1,3,4-thiadiazole derivatives as inhibitors of Entamoeba histolytica

Medicinal Chemistry Research

Volumn 22, Issue 3, 2013, Pages 1305-1312

  Siddiqui, Shadab Miyan ^a   Salahuddin, Attar ^a   Azam, Amir ^a  

^a JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

Author keywords

1,3,4 Thiadiazole; Anti amoebic activity; E. histolytica; HM1:IMSS; MTT assay

Indexed keywords

1,3,4 THIADIAZOLE DERIVATIVE; 2 (5 ANILINO 1,3,4 THIADIAZOL 2 YL)BENZENETHIOL; 2 (5 ANILINO 1,3,4 THIADIAZOLE 2 YL)PHENOL; 5 (2 AMINOPHENYL) N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 (4 CHLOROPHENYL) N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 (4 FLUOROPHENYL) N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 (4 NITROPHENYL) N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 METHYL N PHENYL 1,3,4 THIADIAZOL 2 AMINE; 5 PHENYL 1,3,4 THIADIAZOLE 2 AMINE; 5 PHENYL 1,3,4 THIADIAZOLE 2 THIOL; ANTIAMEBIC AGENT; METRONIDAZOLE; N,5 DIPHENYL 1,3,4 THIDIAZOL 2 AMINE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; BROTH DILUTION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ASSAY; CELL STRAIN MCF 7; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENTAMOEBA HISTOLYTICA; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INFRARED SPECTROSCOPY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 84874108635     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0107-x     Document Type: Article

References (25)

1. Abid A, Bhat AR, Athar F, Azam A (2009) Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2- pyrazolines. Eur J Med Chem 44:417-425
2. Ali TE, Kazak ME (2010) Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties. Eur J Chem 1:6-11
3. Astelbauer F, Walochnik J (2011) Antiprotozoal compounds: state of the art and new developments. Int J Antimicrob Agents 38:118-124
4. Carvalho SA, Silva EFD, Rita RMS, Castro SLD, Fraga CAM (2004) Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2- arylhydrazone derivatives, designed as non-mutagenic megazol analogues. Bio Med Chem Lett 14:5967-5970
5. Chubb FL, Nissenbaum J (1959) Some hypoglycemic thiadiazoles. Can J Chem 37:1121-1123
6. Clerici F (2002) Thiazole and thiadiazole S oxide. Advs Hetrocycl Chem 83:72-115
7. Fardmoghadam MB, Poorrajab F, Kaboudanian S, Emami AS, Shafiee A, Foroumadi A (2008) Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl) -1,3,4-thiadiazol-2-yl]-4-aroylpiperazines. Bioorg Med Chem 16:4509-4515
8. Furniss BS, Rogers V, Smith PWG, Tatchell AR (1989) Vogel's textbook of practical organic chemistry. Longman Scientific and Technical, Essex
9. Gillin FD, Reiner DS, Suffness M (1982) Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. Antimicrob Agents Chemother 22:342-345
10. Hayat F, Salahuddin A, Zargan J, Azam A (2010) Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). Eur J Med Chem 45:6127-6134
11. Hwang EW, Cheung L, Mojtahed A, Cartwright CA (2011) Relapse of intestinal and hepatic amebiasis after treatment. Dig Dis Sci 56:677-680
12. Iqbal R, Zamani K, Rama NH (1996) Synthesis of 2,4-dihydro-4-(2- phenylethyl)-5-(isomericpyridyl)-3H-1,2,4-triazole-3-thiones and their derivatives. Tr J Chem 20:295-301
13. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
14. Park WB, Choe PG, Jo JH, Kim SH, Bang JH et al (2007) Amebiasis in HIV-1-infected Japanese Men: clinical features and response to therapy. Emerg Infect Dis 13:516-517
15. Poorrajab F, Ardestani SK, Emami S, Fardmoghadam MB, Shafiee A, Foroumadi A (2009a) Nitroimidazolyl-1,3,4-thiadiazole-based anti-leishmanial agents: synthesis and in vitro biological evalution. Eur J Med Chem 44:1758-1762
16. Poorrajab F, Ardestani SK, Foroumadi A, Emami S, Kariminia A, Fardmoghadam MB, Shaffie A (2009b) Selective leishmanicidal effect of 1,3,4-thiadiazole derivatives and possible mechanism of action against Leishmania species. Exp Parasitol 121:323-330
17. Rakitin OA (2009) One-pot synthesis of sulfur heterocycles from simple organic substrates. Arkivoc 1:129-149
18. Ralston KS, Petri WA (2011) The ways of a killer: how does Entamoeba histolytica elicit host cell death? Essays Biochem 51:193-210
19. Reid JR, Heindel ND (1976) Improved syntheses of 5-substituted-4-amino-3- merapto- (4H)-1,3,4-triazoles. J Heterocycl Chem 13:925-928
20. Serban G, Cuc S, Egri E, Salvan A (2010) Synthesis of some 2-R-5 formyl-1,3,4- thiadiazole derivatives by sommelet reaction. Farmacia 58:818-824
21. Siddiqui NA, Bawa S, Ali R, Afzal A, Akhtar MJ, Azad B, Kumar R (2011) Antidepressant potential of nitrogen containing heterocyclc moieties: an upgrade review. J Pharm Bioallied Sci 3:194-212
22. Singh S, Athar F, Maurya MR, Azam A (2006) Cyclooctadiene Ru(II) complexes of thiophene-2-carboxaldehyde-derived thiosemicarbazone: synthesis, characterization and antiamoebic activity. Eur J Med Chem 41:592-598
23. Tengku SA, Norhayati M (2011) Public health and clinical importance of amoebiasis in Malasia: a review. Trop Biomed 28:194-222
24. Watanabe K, Gatanaga H, Escueta-de Cadiz A, Tanuma J, Nozaki T, Oka S (2011) Amebiasis in HIV-1 infected Japanese men: clinical features and response to therapy. PLoS Negl Trop Dis 5:1318
25. Wright CW, O'Neill MJ, Phillipson JD, Warhurst DC (1988) Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. Antimicrob Agents Chemother 32:1725-1729