Thioureides of 2-(phenoxymethyl)benzoic acid 4-R substituted: A novel class of anti-parasitic compounds

Parasitology International

Volumn 58, Issue 2, 2009, Pages 128-135

  Müller, Joachim ^a   Limban, Carmen ^b   Stadelmann, Britta ^a   Missir, Alexandru Vasile ^b   Chirita, Ileana Cornelia ^b   Chifiriuc, Mariana Carmen ^c   Nitulescu, George Mihai ^b   Hemphill, Andrew ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b CAROL DAVILA UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^c UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

2 (4 R phenoxymethyl)benzoic acid thioureides; Echinococcus multilocularis; Giardia lamblia; Reporter gene; Screening; Toxoplasma gondii

Indexed keywords

2 (PHENOXYMETHYL)BENZOIC ACID; ANTIPARASITIC AGENT; BENZOIC ACID DERIVATIVE; UNCLASSIFIED DRUG; THIOUREA;

ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CELL STRAIN CACO 2; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLON CANCER; ECHINOCOCCUS MULTILOCULARIS; FIBROBLAST; GIARDIA LAMBLIA; HUMAN; HUMAN CELL; HUMAN TISSUE; IC 50; INFRARED SPECTROSCOPY; MELTING POINT; METACESTODE; PARASITE; PREPUCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TOXOPLASMA GONDII; ANALOGS AND DERIVATIVES; ANIMAL; CACO 2 CELL LINE; CHEMISTRY; DRUG EFFECTS; DRUG SENSITIVITY; GIARDIA INTESTINALIS; GROWTH, DEVELOPMENT AND AGING; LARVA; TOXOPLASMA;

ANIMALS; ANTIPARASITIC AGENTS; BENZOIC ACIDS; CACO-2 CELLS; ECHINOCOCCUS MULTILOCULARIS; FIBROBLASTS; GIARDIA LAMBLIA; HUMANS; LARVA; PARASITIC SENSITIVITY TESTS; THIOUREA; TOXOPLASMA; BENZOATES;

ECHINOCOCCUS MULTILOCULARIS; GIARDIA INTESTINALIS; PROTOZOA; TOXOPLASMA GONDII;

EID: 67349119905     PISSN: 13835769     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.parint.2008.12.003     Document Type: Article

References (35)

1. Cassell G.H., and Mekalanos J. Development of antimicrobial agents in the era of new and reemerging infectious diseases and increasing antibiotic resistance. J Am Med Ass 285 (2001) 601-605
2. Egan T.J., and Kaschula C.H. Strategies to reverse drug resistance in malaria. Curr Opin Infect Dis 20 (2007) 598-604
3. Gardner T.B., and Hill D.R. Treatment of Giardiasis. Clin Microbiol Rev 14 (2001) 114-128
4. Chavez B., Espinosa-Cantellano M., Cedillo-Rivera R Ramírez A., and Martínez-Palomo A. Effects of albendazole on Entamoeba histolytica and Giardia lamblia trophozoites. Arch Med Res 23 (1992) 63-67
5. Müller J., Sterck M., Hemphill A., and Müller N. Characterization of Giardia lamblia WB C6 clones resistant to nitazoxanide and to metronidazole. J Antimicrob Chemother 60 (2007) 280-287
6. Innes E.A., and Vermeulen A.N. Vaccination as a control strategy against the coccidial parasites Eimeria, Toxoplasma and Neospora. Parasitology 133 (2007) S145-S168
7. McAllister M.M. A decade of discoveries in veterinary protozoology changes our concept of "subclinical" toxoplasmosis. Vet Parasitol 132 (2005) 241-247
8. Murphy K., Groarke M., O'Shaugnessy E., Buckley A., and Mitchell T. Pyrimethamine alone as long-term suppressive therapy in cerebral toxoplasmosis. Am J Med 96 (1994) 95-96
9. Petersen E. Prevention and treatment of congenital toxoplasmosis. Exp Rev Anti-inf Ther 5 (2007) 285-293
10. Hemphill A., Spicher M., Stadelmann B., Müller J., Naguleswaran A., Gottstein B., et al. Innovative chemotherapeutical treatment options for alveolar and cystic echinococcosis. Parasitology 134 (2007) 1657-1670
11. Hemphill A., Müller J., and Esposito M. Nitazoxanide, a broad-spectrum thiazolide anti-infective agent for the treatment of gastrointestinal infections. Expert Opin Pharmacother 7 (2006) 953-964
12. Hemphill A., Müller N., and Müller J. Structure-function relationship of thiazolides, a novel class of anti-parasitic drugs, investigated in intracellular and extracellular protozoan parasites and larval-stage cestodes. Antiinf Agents Med Chem 6 (2007) 273-282
13. Monaghan R.L., and Barrett J.F. Antibacterial drug discovery - then, now and the genomics. Biochem Pharmacol 71 (2006) 901-909
14. Kayser O., Kiderlen A.F., and Croft S.L. Natural products as antiparasitic drugs. Parasitol Res 90 (2003) S55-S62
15. Fox L.M., and Saravolatz L.D. Nitazoxanide: a new thiazolide antiparasitic agent. Rev Antiinf Agents 40 (2005) 1173-1180
16. Esposito M., Stettler R., Moores S.L., Pidathala C., Müller N., Stachulski A., et al. In vitro efficacies of nitazoxanide and other thiazolides against Neospora caninum reveal anti-parasitic activity independent of the nitro group. Antimicrob Agents Chemother 49 (2005) 3715-3723
17. Chou A.W. 1-[3,4-Bis[3-(lower-alkoxycarbonyl)-2-thioureido]phenyl]-1-phenylethylen es. Bv USA (1984) 4438135 (Cl 424-300; C07C157/12)
18. Desai K.R., and Desai P.H. Synthesis and antibacterial activity of 2,4-bis(4-methoxyanilino)-6-(N-arylthioureido-N′-aminoacyl)-s-tria sine derivatives. J Inst Chem 61 (1989) 19-20
19. Kapoor K.K., Somal P., Gupta R., and Kachroo P.L. Synthesis and antimicrobial activity of some 5-aryl-2-[N-(5-nitrofurfurylidene)amino]- and 5-aryl-2-(N-thiocarbamoylamino)-1,3,4-oxadiazoles. J Indian Chem Soc 68 (1991) 104-106
20. Lueshun J., Yulu W., Yongfang L., Fangshu H., and Yuyfang S. Synthesis of 1-aroyl-3-(4-benzosulphonamido-pyrimidine)-thioureas. Yougi Huaxue 13 (1993) 250-252
21. Balotescu M.C., Limban C., Missir A., Chirita I., and Nitulescu G.M. The synthesis and biological activities of some new 2-(4-methoxy-phenoxymethyl)benzoic acid thioureides. Rev Chim (Bucur) 58 (2007) 1064-1068
22. Limban C., Balotescu M.C., Missir A., Chirita I., and Bleotu C. Antimicrobial activity of some new thioureides derived from 2-(4-chlorophenoxymethyl)benzoic acid. Molecules 13 (2008) 567-580
23. Limban C., Missir A.l., and Chiriţǎ I. New thioureides of 2-phenoxymethyl-benzoyl acid. Note no. 1. Farmacia 48 6 (2000) 73-78
24. Limban C., Missir A.l., and Chiriţǎ I. New thioureides of 2-phenoxymethylbenzoic acid. Note no. 2. Farmacia 52 (2004) 7-12
25. Limban C., Missir A.l., and Chiriţǎ I. Synthesis and characterization of some new thioureides of 2-(4-methoxy-phenoxymethyl)-benzoic acid with potential pharmacological activity. Timis Med J 55 supplement 5 (2005) 42-44
26. Limban C., Missir A.l., Chiriţǎ I., and Missir C. The synthesis and characterization of some new thioureides of 2-(4-methyl-phenoxymethyl)-benzoic acid with potential pharmacological activity. Romanian International Conference on Chemistry and Chemical Engineering- RICCCE XIV, Bucharest, Romania vol. 4 (2005) S-02-99
27. Limban C, Balotescu MC, Missir A, Chirita I, Mihaescu G, Israil A. Antimicrobial activity of some new thioureides of 2-(4-chlorophenoxy)-benzoic Acid. 16th European Congress of Clinical Microbiology and Infectious Diseases., 2006, April 1-4, Nice, France.
28. Esposito M., Moores S., Naguleswaran A., Müller J., and Hemphill A. Induction of tachyzoite egress from cells infected with the protozoan Neospora caninum by nitro- and bromo-thiazolides, a class of broad-spectrum anti-parasitic drugs. Int J Parasitol 37 (2007) 1143-1152
29. Leepin A., Stüdli A., Brun R., Stephens C.E., Boykin D.W., and Hemphill A. Host cells participate in the in vitro effects of new-generation diamidine-analogues against tachyzoites of the intracellular apicomplexan parasites Neospora caninum and Toxoplasma gondii. Antimicrob Agents Chemother 52 (2008) 1999-2008
30. Spiliotis M., Lechner S., Tappe D., Scheller C., Krohne G., and Brehm K. Transient transfection of Echinococcus multilocularis primary cells and complete in vitro regeneration of metacestode vesicles. Int J Parasitol 38 (2008) 1025-1039
31. McFadden D.C., Seeber F., and Boothroyd J.C. Use of Toxoplasma gondii expressing β-galactosidase for colorimetric assessment of drug activity in vitro. Antimicrob Agents Chemother 41 (1997) 1849-1853
32. Hemphill A., and Croft S.L. Electron microscopy in parasitology. In: Rogan M. (Ed). Analytical Parasitology (1997), Springer Verlag, Heidelberg 227-268
33. Boscencu R., Nacea V., Limban C., Missir A., and Socoteanu R. Transitional metals with new N,N′-disubstituted phenyl thiourea. Rev Chim (Bucur) 58 (2007) 16-19
34. Nacea V., Boscencu R., Missir A., Limban C., and Barbuceanu S. The synthesis and characterization of some complex combinations of Cu (I) and Cu (II) with new N,N′-disubstituted thiourea. Rev Chim (Bucur) 56 (2005) 68-71
35. Olar R., Badea M., Cristurean E., Lazar V., Cernat R., and Balotescu C. Thermal behavior, spectroscopic and biological characterization of Co (II), Zn (II) and Pt (II) complexes with N,N-dimethylbiguanide. J Therm Anal Calorim 80 (2005) 451-455