Synthesis of some novel triazole derivatives and investigation of their antimicrobial activities

Synthetic Communications

Volumn 41, Issue 15, 2011, Pages 2234-2250

  Altintop, Mehlika Dilek ^a   Kaplancikli, Zafer Asim ^a   Turan Zitouni, Gülhan ^a   Özdemir, Ahmet ^a   Demirci, Fatih ^a   Işcan, Gökalp ^a   Revial, Gilbert ^b  

^a ANADOLU UNIVERSITY   (Turkey)

^b CNRS   (France)

Author keywords

Antimicrobial activity; Benzothiazole; Triazole

Indexed keywords

2 CHLORO N (BENZOTHIAZOLE 2 YL)ACETAMIDE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 2,4 DIHYDRO 3H 1,2,4 TRIAZOL 3 THIONE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 3 [N (6 CHLOROBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 3 [N (6 ETHOXYBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 3 [N (6 METHOXYBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 3 [N (6 METHYLBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 (2 CYCLOHEXYLETHYL) 3 [N (BENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 2,4 DIHYDRO 3H 1,2,4 TRIAZOL 3 THIONE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (6 CHLOROBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (6 ETHOXYBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (6 METHOXYBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (6 METHYLBENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (BENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE; 4 AMINO 5 [2 (4 HYDROXYPHENYL)ETHYL] 3 [N (BENZOTHIAZOLE 2 YL)ACETAMIDO]THIO 4H 1,2,4 TRIAZOLE DERIVATIVE; N (BENZOTHIAZOL 2 YL) 2 CHLOROACETAMIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 79957635690     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.501475     Document Type: Article

References (18)

1. Fridkin, S. K.; Jarvis, W. R. Epidemiology of nosocomial fungal infections. Clin. Microbiol. Rev. 1996, 9(4), 499-511. (Pubitemid 26366535)
2. Pfaller, M. A.; Diekema, D. J. Epidemiology of invasive Candidiasis: A persistent public health problem. Clin. Microbiol. Rev. 2007, 20(1), 133-163. (Pubitemid 46167771)
3. Sims, C. R.; Ostrosky-Zeichner, L.; Rex, J. H. Invasive Candidiasis in immunocompromised hospitalized patients. Arch. Med. Res. 2005, 36, 660-671. (Pubitemid 41436235)
4. Eggimann, P.; Garbino, J.; Pittet, D. Epidemiology of Candida species infections in critically ill nonimmunosuppressed patients. Lancet Infect. Dis. 2003, 3, 685-702. (Pubitemid 37345347)
5. Ruan, S. Y.; Hsueh, P. R. Invasive Candidiasis: An overview from Taiwan. J. Formos. Med. Assoc. 2009, 108(6), 443-451.
6. Spellberg, B. J.; Filler, S. G.; Edwards, Jr., J. E. Current treatment strategies for disseminated Candidiasis. Clin. Infect. Dis. 2006, 42, 244-251. (Pubitemid 43054198)
7. Odds, F. C.; Brown, A. J. P.; Gow, N. A. R. Antifungal agents: Mechanisms of action. Trends Microbiol. 2003, 11, 272-279. (Pubitemid 36725017)
8. Williams, D. A.; Lemke, T. L. Foye's Principles of Medicinal Chemistry, 5th ed.; Lippincott Williams & Wilkins: Baltimore, 2002; pp. 891-903.
9. Sheehan, D. J.; Hitchcock, C. A.; Sibley, C. M. Current and emerging azole antifungal agents. Clin. Microbiol. Rev. 1999, 12(1), 40-79. (Pubitemid 29055953)
10. Canuto, M. M., Rodero, F. G. Antifungal drug resistance to azoles and polyenes. Lancet Infect. Dis. 2002, 2, 550-563. (Pubitemid 34966358)
11. Ghannoum, M. A.; Louis, B. R. Antifungal agents: Mode of action, mechanisms of resistance and correlation of these mechanisms with bacterial resistance. Clin. Microbiol. Rev. 1999, 12(4), 501-517. (Pubitemid 29484744)
12. Shaker, R. M. The chemistry of mercapto- and thione-substituted 1,2,4-triazoles and their utility in heterocyclic synthesis. Arkivoc 2006, 9, 59-112. (Pubitemid 44131317)
13. Ali, T. E. Utility of thiocarbohydrazide in heterocyclic synthesis. J. Sulfur Chem. 2009, 30(6), 611-647.
14. Bhargava, P. N.; Ram, P. Synthesis of local anesthetics. Bull. Chem. Soc. Japan 1965, 38(3), 339-41.
15. Kuranari, M.; Takeuchi, H. 1,2,4-triazole derivatives. Jpn. Patent 21,420, 1963.
16. Blackman, A. J.; Polya, J. B. Triazoles, part XI: Synthesis of 1,2,4-triazole-3-sulphonic acids by oxidation of 1,2,4-triazoline-3-thiones. J. Chem. Soc. C 1970, 2403-2409.
17. National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard, 2nd ed.; NCCLS: Wayne, PA, 2002.
18. Poyraz, M.; Sari, M.; Guney, A.; Demirci, F.; Demirayak, S.; Sahin, E. Synthesis, characterization, and antimicrobial activity of a Zn(II) complex with 1-(1H-benzoimidazol- 2-yl)-ethanone thiosemicarbazone. J. Coord. Chem. 2008, 61(20), 3276-3283.