Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives

Medicinal Chemistry Research

Volumn 22, Issue 7, 2013, Pages 3134-3147

  Popiołek, Łukasz ^a   Kosikowska, Urszula ^a   Mazur, Liliana ^b   Dobosz, Maria ^a   Malm, Anna ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^b MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

1,2,4 Triazole derivatives; 1,3,4 Thiadiazole derivatives; Antimicrobial activity

Indexed keywords

1,2,4 THIADIAZOLE DERIVATIVE; 1,2,4 TRIAZOLE DERIVATIVE; 4 (4 BROMOPHENYL) 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 (4 BROMOPHENYL) 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 (4 CHLOROPHENYL) 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL) SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 (4 CHLOROPHENYL) 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 (4 METHOXYBENZYL) 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 (4 METHOXYBENZYL) 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 (4 METHOXYPHENYL) 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 (4 METHOXYPHENYL) 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 ALLYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] ACETYL] THIOSEMICARBAZIDE; 4 ALLYL 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 BENZOYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 BENZYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] ACETYL] THIOSEMICARBAZIDE; 4 BENZYL 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 CYCLOHEXYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 CYCLOHEXYL 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 ETHOXYCARBONYL 1 [[(4,5DIPHENYL 4H 1,2,4 TRIAZOL 3 YL) SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 ETHOXYCARBONYLMETHYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]ACETYL] THIOSEMICARBAZIDE; 4 ETHYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] ACETYL] THIOSEMICARBAZIDE; 4 ETHYL 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4 PHENYL 1 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] ACETYL] THIOSEMICARBAZIDE; 4 PHENYL 5 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL] 4H 1,2,4 TRIAZOLE 3(2H) THIONE; 4,5 DIPHENYL 4H 1,2,4 TRIAZOLE 3 THIONE; 5 AMINOALLYL 2 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL]1,3,4 THIADIAZOLE; 5 AMINOCYCLOHEXYL 2 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL) SULFANYL]METHYL] 1,3,4 THIADIAZOLE; 5 AMINOETHYL 2 [[(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL]METHYL] 1,3,4 THIADIAZOLE; [(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL)SULFANYL] ACETOHYDRAZIDE; ETHYL 2 [(4,5 DIPHENYL 4H 1,2,4 TRIAZOL 3 YL) SULFANYL]ACETATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AGAR DILUTION; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SPECTROSCOPY; STAPHYLOCOCCUS AUREUS;

EID: 84878852421     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0302-9     Document Type: Article

References (40)

1. Allen FH (2002) The Cambridge Structural Database: a quarter of million crystal structures and rising. Acta Crystallogr B 58:380-388
2. Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A (2004) Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg Med Chem Lett 14:6057-6059
3. Al-Soud YA, Al-Dweri MN, Al-Masoudi NA (2004) Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives. Farmaco 59:775-783
4. Bailey EM, Krakovsky DJ, Rybak M (1990) The triazole antifungal agents: a review of itraconazole and fluconazole. Pharmacotherapy 10:146-153
5. Bourgeois I, Pestel-Caron M, Lemeland JF, Pons JL, Caron F (2007) Tolerance to the glycopeptides vancomycin and teicoplanin in coagulase-negative Staphylococci. Antimicrob Agents Chemother 51(2):740-743
6. Clemons M, Coleman RE, Verma S (2004) Cancer Treat Rev 30:325-332
7. CLSI (2008) Performance standards for antimicrobial susceptibility testing; Eighteenth International Supplement. CLSI document M7-MIC. Clinical Laboratory Standards Institute, Wayne
8. Collin X, Sauleau A, Coulon J (2003) 1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents. Bioorg Med Chem Lett 13:2601-2605
9. Demirbas A, Sahin D, Demirbas N, Karaoglu SA (2009) Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Eur J Med Chem 44:2896-2903
10. Dobosz M, Pachuta-Stec A (1995) Cyclization of 1-cyanoacetyl-4- substituted thiosemicarbazides to 1,2,4-triazole or 1,3,4-thiadiazole derivatives. Acta Pol Pharm 52:103-111
11. 2-1,2,4-triazoline-5-thione and 5-benzyl-1,3,4- thiadiazole. Acta Pol Pharm 53:123-131
12. Dobosz M, Pitucha M, Wujec M (1996) The reactions of cyclization of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system. Acta Pol Pharm 53:31-38
13. Dogan HN, Duran A, Rollas S, Sener G, Uysal MK, Gülen D (2002) Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities. Bioorg Med Chem 10:2893-2898
14. Duran A, Dogan HN, Rollas S (2002) Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4- triazoline-5-thiones. Farmaco 57:559-564
15. El Shehry MF, Abu-Hashem AA, El-Telbani EM (2010) Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur J Med Chem 45:1906-1911
16. Gadad AK, Noolvi MN, Karpoormath RV (2004) Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo-[2,1-b]-1,3,4-thiadiazole derivatives. Bioorg Med Chem 12:5651-5659
17. Gülerman NN, Doǧan HN, Rollas S, Johansson C, Çelik C (2001) Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Farmaco 56:953-958
18. Harish K, Sadique AJ, Suroor AK, Mohammad A (2008) 1,3,4-Oxadiazole/ thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties. Eur J Med Chem 43:2688-2698
19. Holmwood G, Buechel KH, Plempel M, Haller J (1982) Antimicrobial azoles. Chem Abstr 96:62979s. Patent RFN DE 3018865, 1981
20. Kaplaushenko AH, Panasenko OI, Knish EH, Scherbina RO (2008) Synthesis, physicochemical and biological properties of 2-(5-R1-4-R2-1,2,4-triazol-3- ylthio)acetic acids. Farm Zh 2:67-72
21. Klimešová V, Zahajská L, Waisser K, Kaustová J, Möllmann U (2004) Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Farmaco 59:279-288
22. Kumar D, Kumar NM, Chang K-H, Shah K (2010) Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. Eur J Med Chem 45:4664-4668
23. Liesen AP, De Aquino TM, Carvalho CS, Lima VT, De Araújo JM, De Lima JG, De Faria AR, De Melo EJT, Alves AJ, Alves EW, Alves AQ, Góes AJS (2010) Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles. Eur J Med Chem 45:3685-3691
24. McGinnis MR, Pasarell L, Sutton DA, Fothergill AW, Cooper CR, Rinaldi MG (1997) Antimicrob Agents Chemother 41:1832-1834
25. Oxford Diffraction, Xcalibur CCD System (2006) CrysAlis Software System, Version 1.171. Oxford Diffraction Ltd., Abingdon
26. Padmavathi V, Sudhakar Reddy G, Padmaja A, Kondaiah P, Ali-Shazia (2009) Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem 44:2106-2112
27. Pick C (1997) Antinociceptive interaction between alprazolam and opioids. Brain Res Bull 42:239-243
28. Ramasubbu N, Parthasarathy R (1989) Short S.O contacts: structure of 2,5-bis(p-methoxyphenylhydroxymethyl)thiophene. Acta Crystallogr C 45:457-460
29. Schenone S, Brullo C, Bruno O, Bondavalli F, Ranise A, Filippelli W et al (2006) New 1,3,4-thiadiazole derivatives endowed with analgesic and anti-inflammatory activities. Bioorg Med Chem 14:1698-1705
30. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112-122
31. Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, Kalyan ChA, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M (2007) Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents. Bioorg Med Chem 15:3997-4008
32. Shiroki M, Tahara T, Araki K (1976) Chem Abstr 84:59588k. Japanese Patent 75100096, 1975
33. Siwek A, Paneth P (2007) Computational studies of the cyclization of thiosemicarbazides. J Phys Org Chem 20:463-468
34. Siwek A, Wujec M, Dobosz M, Wawrzycka-Gorczyca I (2010) Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides. Heteroat Chem 21(7):521-532
35. Turan-Zitouni G, Kaplancikli ZA, Erol K, Kiliç FS (1999) Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Farmaco 54:218-223
36. Ulusoy N, Gürsoy A, Ötük G (2001) Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco 56:947-952
37. Wei Q-L, Zhang S-S, Gao J, Li W-H, Xu L-Z, Yu Z-G (2006) Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents. Bioorg Med Chem 14:7146-7153
38. White EL, Suling WJ, Ross LJ, Seitz LE, Reynolds RC (2002) 2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ. J Antimicrob Chemother 50:111-114
39. Wilson AJC (ed) (1995) International tables for crystallography, vol C. Kluwer Academic Publishers, Dordrecht
40. Wujec M, Paneth P (2007) Mechanism of 4-methyl-1,2,4-triazol-3-thiole reaction with formaldehyde. A DFT study. J Phys Org Chem 20:1043-1049