Synthesis, characterization and evaluation of antibacterial activity of some thiazolo[3,2-b][1,2,4]triazole incorporating diphenylsulfone moieties

European Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2009, Pages 4752-4757

  Barbuceanu, Stefania Felicia ^a   Almajan, Gabriela Laura ^a   Saramet, Ioana ^a   Draghici, Constantin ^b   Tarcomnicu, Ana Isabela ^c   Bancescu, Gabriela ^d  

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

^b INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

^c Pharma Serv International   (Romania)

^d Faculty of Dentistry   (Romania)

Author keywords

(Phenylsulfonyl)phenyl moiety; 5 Substituted 1,2,4 triazole 3 thiole; Alkylation; Antibacterial activity; Thiazolotriazole

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 2 [4 (4 X PHENYLSULFONYL)PHENYL)[1,3]THIAZOLO[3,2 B] [1,2,4] TRIAZOLE DERIVATIVE; 4 BROMOPHENACYL BROMIDE; 4 BROMOPHENCYL BROMIDE; 5 [4 (4 X PHENYLSULFONYL)PHENYL] 4H 1,2,4 TRIAZOLE 3 THIOLE DETRIVATIVE; DIPHENYL SULFONE; SULFONE; THIAZOLO[3,2 B][1,2,4]TRIAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACINETOBACTER BAUMANNII; ALKYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTI-BACTERIAL AGENTS; BACTERIA; BIPHENYL COMPOUNDS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES; TRIAZOLES;

EID: 70349775537     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.06.021     Document Type: Article

References (39)

1. Ezabadi I.R., Camoutsis C., Zoumpoulakis P., Geronikaki A., Sokovic M., Glamočilija J., and Ćirić A. Bioorg. Med. Chem. 16 (2008) 1150-1161
2. Goswami B.N., Kataky J.C.S., and Baruah J.N. J. Heterocycl. Chem. 21 (1984) 1225-1229
3. Abd El-Salam O.I., and Mohamed S.F. J. Chin. Chem. Soc. 52 (2005) 1157-1164
4. Kidwai M., and Mohan R. J. Korean Chem. Soc. 48 (2004) 177-180
5. Siddiqui A.A., Arora A., Siddiqui N., and Misra A. Indian J. Chem. Sect. B 44 (2005) 838-841
6. Küçükgüzel I., Küçükgüzel S.G., Rollas S., and Kiraz M. Bioorg. Med. Chem. Lett. 11 (2001) 1703-1707
7. Tozkoparan B., Küpeli E., Yeşilada E., and Ertan M. Bioorg. Med. Chem. 15 (2007) 1808-1814
8. Amir M., and Kumar S. Acta Pharm. 57 (2007) 31-45
9. Ceylan Ünlüsoy M., Bozdag Dündar O., Altanlar N., and Ertan R. Turk. J. Chem. 30 (2006) 355-360
10. Sup R.C., Sup R.Y., and Bang C.W. Korean J. Med. Chem. 5 (1995) 72-75
11. Agarwal N., Kumar S., Shrivastava A.K., and Sarkar P.C. Indian J. Heterocycl. Chem. 6 (1997) 291-294
12. Geronikaki A., and Hadjipavlou-Litina D. Arzneim. Forsc./Drug Res. 46 (1996) 1134-1138
13. Bénéteau V., Besson T., Guillard J., Leonce S., and Pfeiffer B. Eur. J. Med. Chem. 34 (1999) 1053-1060
14. Erol D.D., Çaliş U., Demirdamar R., Yuluǧ N., and Ertan M.J. Pharm. Sci. 84 (1995) 462-465
15. El-Sherif H.A.H., Mahmoud A.M., Sarhan A.A.O., Hozien Z.A., and Habib O.M.A. J. Sulfur Chem. 27 (2006) 65-85
16. Karthikeyan M.S. Eur. J. Med. Chem. (2008) 10.1016/j.ejmech.2008.04.022
17. Tozkoparan B., Gökhan N., Küpeli E., Yeşilada E., and Ertan M. Arzneim. Forsc./Drug Res. 54 (2004) 35-41
18. Berk B., Aktay G., Yesilada E., and Ertan M. Pharmazie 56 (2001) 613-616
19. Roy P., Leblanc Y., Ball R.G., Brideau C., Chan C.C., Chauret N., Cromlish W., Ethier D., Gauthier J.Y., Gordon R., Greig G., Guay J., Kargman S., Lau C.K., O'Neil G., Silva J., Thérien M., van Staden C., Wong E., Xu L., and Prasit P. Bioorg. Med. Chem. Lett. 7 (1997) 57-62
20. Pignatello R., Mazzone S., Panico A.M., Mazzone G., Pennisi G., Castana R., Matera M., and Blandino G. Eur. J. Med. Chem. 26 (1991) 929-934
21. Lesyk R., Vladzimirska O., Holota S., Zaprutko L., and Gzella A. Eur. J. Med. Chem. 42 (2007) 641-648
22. Demirayak S., .Zitouni G., Chevallet P., Erol K., and Kiliç F.S. Il Farmaco 48 (1993) 707-712
23. Elslager E.F., Gavrilis Z.B., Phillips A.A., and Worth D.F. J. Med. Chem. 12 (1969) 357-363
24. Wolf R., Matz H., Orion E., Tuzun B., and Tuzun Y. Dermatol. Online J. 8 (2002) 2
25. Barbuceanu S.F., Saramet I., Almajan G.L., Draghici C., Tarcomnicu I., and Bancescu G. Rev. Chim. (Bucharest) 59 (2008) 963-968
26. Almajan G.L., Barbuceanu S.F., Saramet I., Draghici C., and Socoteanu R. Rev. Chim. (Bucharest) 58 (2007) 56-59
27. Saramet I., Almajan G.L., Barbuceanu S., Draghici C., and Banciu M.D. Rev. Roum. Chim. 50 (2005) 19-27
28. Saramet I., Banciu M.D., and Draghici C. Rev. Roum. Chim. 36 (1991) 135-143
29. Mavrodin A., Zotta V., Stoenescu V.M., and Oteleanu D. Pharm. Zentr. Deutsch. 95 (1956) 353-361
30. Pots K.T., and Husain S. J. Org. Chem. 36 (1971) 10-13
31. Burbuliene M.M., Jakubkiene V., Mekuskiene G., and Vainilavicius P. Phosphorus Sulfur Silicon Relat. Elem. 178 (2003) 2431-2440
32. Barry A. Procedures and Theoretical Considerations for Testing Antimicrobial Agents in Agar Media. In: Lorian (Ed). Antibiotics in Laboratory Medicine. fifth ed (1991), Williams and Wilkins, Baltimore
33. National Committee for Clinical Laboratory Standard, NCCLS: Methods for antimicrobial dilution and disk susceptibility testing of infrequently isolated or fastidious bacteria; Approved guideline, Document M45-A 26(19). Willanova PA, USA, 1999.
34. Britsun V.N., Esipecko A.N., and Lozinskii M.O. Chem. Heterocycl. Compd. 41 (2005) 782-786
35. Simiti I., Demian H., Marie A., and Palibroda N. Org. Mass Spectrosc. 15 (1980) 172-174
36. Zaharia V., and Chirtoc I. Farmacia XLIX (2001) 24-31
37. Mazzone G., and Reina Avrigo R. Boll. Chem. Farm. 112 (1973) 35-44
38. Mazzone G., Puglisi G., Carsaro A., Panico A.M., Bonina F., Roxas Amico M., and Trombadore S. Eur. J. Med. Chem. 21 (1986) 277-284
39. Temple Jr. C. In: Montgomery J.A. (Ed). Triazoles 1,2,4 (1981), Wiley & Sons, New York 251-258