Synthesis, characterization and antimicrobial studies of 2-(4-methoxy-phenyl)-5-methyl-4-(2-arylsulfanyl-ethyl)-2,4-dihydro-[1,2,4] triazolo-3-ones and their corresponding sulfones

European Journal of Medicinal Chemistry

Volumn 45, Issue 8, 2010, Pages 3329-3334

  Patil, Bhimagouda S ^a,b   Krishnamurthy, G ^b   Naik, H Bhojya ^c,d   Latthe, Prashant R ^a   Ghate, Manjunath ^b  

^a SYNGENE INTERNATIONAL LTD   (India)

^b Sahyadri Science College   (India)

^c KUVEMPU UNIVERSITY   (India)

^d KRUPANIDHI COLLEGE OF PHARMACY   (India)

Author keywords

1,2,4 Triazolo 3 ones; Antimicrobial activity; Sulfones; Thioethers; Thiols

Indexed keywords

2 (4 METHOXYPHENYL) 4 [2 (3 METHOXYPHENYLSULFANYL)ETHYL] 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 2 (4 METHOXYPHENYL) 5 METHYL 4 [2 (3 TRIFLUOROMETHYLBENZENESULFONYL)ETHYL] 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 2 (4 METHOXYPHENYL) 5 METHYL 4 [2 (3 TRIFLUOROMETHYLPHENYLSULFANYL)ETHYL] 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 (2 BENZENESULFONYLETHYL) 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 (2 PHENYLSULFANYLETHYL) 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (2 FLUOROBENZENESULFONYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (2 FLUOROPHENYLSULFANYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (3 FLUOROBENZENESULFONYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (3 FLUOROPHENYLSULFANYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (4 AMINOPHENYLSULFANYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (4 BROMOBENZENESULFONYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (4 BROMOPHENYLSULFANYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (4 FLUOROBENZENESULFONYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 (4 FLUOROPHENYLSULFANYL)ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; 4 [2 [5 (4 CHLOROPHENYL) [1,3,4]OXADIAZOL 2 YL SULFANYL]ETHYL] 2 (4 METHOXYPHENYL) 5 METHYL 2,4 DIHYDRO[1,2,4]TRIAZOL 3 ONE; SULFONE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; RHIZOPUS ORYZAE; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 77954314818     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.04.016     Document Type: Article

References (44)

1. N. Demirbas,A. Demirbas,S. Alpay Karaoglu,E. Celik,Arkivoc I (2005) 75-91
2. B. S. Holla,R. Gonsalves,S. Shenoy,Eur. J. Med. Chem. 35 (2000) 267-271
3. A. Shafiee,A. Sayadi,M. H. Roozbahani,A. Foroumadi,F. Kamal,Arch. Pharm. Pharm. Med. Chem. 10 (2002) 495-499.
4. S. Sharma,S. Gangal,A. Rauf,M. Zahin,Arch. Pharm. Chem. Life. Sci. 341 (2008) 714-720.
5. N. N. Gulerman,H. N. Dogan,S. Rollas,C. Johanssom,C. Celik,Il Farmaco 56 (2001) 953-958.
6. S. Papakonstantinou-Garoufalias,N. Pouli,P. Marakos,A. Chytyroglou-Ladas,Il Farmaco 57 (2002) 973-977
7. G. Turan-Zitouni,Z. A. Kaplacikli,M. T. Yildiz,P. Chevallet,D. Kaya,Eur. J. Med. Chem. 40 (2005) 607-613
8. A. R. Jalilian,S. Sattari,M. Bineshmarevasti,A. Shafiee,M. Daneshtalab,Arch. Pharm. Pharm. Med. Chem. 333 (2000) 347-354
9. I. Kucukguzel,S. G. Kucukguzel,S. Rollas,M. Kiraz,Bioorg. Med. Chem. Lett. 11 (2001) 1703-1707.
10. L. Zahajska,V. Klimesova,J. Koci,K. Waisser,J. Kaustova,Arch. Pharm. Pharm. Med. Chem. 337 (2004) 549-555.
11. A. Foroumadi,Z. Kiani,F. Soltani,Il Farmaco 58 (2003) 1073-1076.
12. G. Turan-Zitouni,M. Sivaci,F. S. Kiliç,K. Erol,Eur. J. Med. Chem. 36 (2001) 685-689.
13. B. Tozkoparan,E. Kupeli,E. Yeş ilada,M. Ertan,Bioorg. Med. Chem 15 (2007) 1808-1814.
14. S. M. Rabea,N. A. El-Koussi,H. Y. Hassan,T. Aboul-Fadl,Arch. Pharm. Chem. Life Sci. 339 (2006) 32-40.
15. L. Labanauskas,E. Udrenaite,P. Gaidelis,A. Brukstus,Il Farmaco 59 (2004) 255-259
16. B. S. Holla,B. Veerendra,M. K. Shivananda,B. Poojary,Eur. J. Med. Chem. 38 (2003) 759-767.
17. A. Duran,H. N. Dogan,S. Rollas,Il Farmaco 57 (2002) 559-564
18. A. Almasirad,S. A. Tabatabai,M. Faizi,A. Kebriaeezadeh,N. Mehrabi,A. Dalvandi,A. Shafiee,Bioorg. Med. Chem. Lett. 14 (2004) 6057-6059.
19. I. Kuçukguzel,S. G. Kuçukguzel,S. Rollas,G. Otuk-Sanis,O. Ozdemir,I. Bayrak,T. Altug,J. P. Stables,Il Farmaco 59 (2004) 893-901.
20. M. Kritsanida,A. Mouroutsou,P. Marakos,N. Pouli,S. Papakonstantinou- Garoufalias,C. Pannecouque,M. Witvrouw,E. De Clercq,Il Farmaco 57 (2002) 253-257.
21. M. T. Abdel-Aal,W. A. El-Sayed,S. M. El-Kosy,E. S. H. El-Ashry,Arch. Pharm. Chem. Life Sci. 341 (2008) 307-313.
22. B. Chai,X. Qian,S. Cao,H. Liu,G. Song,Arkivoc Ii (2003) 141-145.
23. A. Varvaresou,T. Siatra-Papastaikoudi,A. Tsotinis,A. Tsantili-Kakoulidou, A. Vamvakides,Il Farmaco 53 (1998) 320-326.
24. B. Modzelewska-Banachiewicz,J. Banachiewicz,A. Chodkowska,E. Jagiello-Wojtowicz,L. Mazur,Eur. J. Med. Chem. 39 (2004) 873-877
25. V. Padmavathi,P. Thriveni,G. Sudhakar Reddy,D. Deepti,Eur. J. Med. Chem. 43 (2008) 917-924.
26. W. T. Ashton,C. L. Cantone,L. L. Chang,S. M. Hutchine,R. A. Strelitz,M. MacCoea,R. S. L. Chang,V. J. Lotti,K. A. Faust,B. Tsing-Chen,P. Bunting,T. W. Schorn,S. D. Kivlighn,P. K. S. Sieglt,J. Med. Chem. 36 (1993) 591-609
27. B. Tozkoparan,E. Kupeli,E. Yesilada,M. Ertan,Bioorg. Med. Chem. 15 (2007) 1808-1814.
28. H. Singh,L. D. S. Yadav,B. K. Bhattacharya,J. Indian Chem. Soc. 56 (10) (1979) 1013-1016.
29. J. R. Vishnu,J. V. Arnold,J. Heterocycl. Chem. 25 (1) (1988) 253-256.
30. B. Tinperciuc,A. Parvu,M. Palage,O. Oniga,D. Ghiran,Farmacia (Bucharest) 47 (1999) 77.
31. I. Angilini,L. Angilini,F. Sparace,British Pat. 1,161,801,1969.
32. Chem. Abstr 71 (1969) 112936.
33. C. Baozhen,Q. Weizhong,S. Zhengwu,L. Xinghan,Y Gongye,16 (1985) 305
34. Chem. Abstr 104 (1986) 186357.
35. E. Palaska,G. Sahin,P. Kelicen,N. T. Durlu,G. Altinok,Il Farmaco 57 (2002) 101-107.
36. M. D. Mullican,M. W. Wilson,D. T. Connor,C. R. Kostlan,D. J. Schrier,R. D. Dyer,J. Med. Chem. 36 (1993) 1090-1099.
37. K. Raman,K. H. Singh,S. K. Salzman,S. S. Parmar,J. Pharm. Sci. 82 (1993) 167-169.
38. S. Shujuan,L. Hongxiang,Y. Gao,P. Fan,B. Ma,W. Ge,X. Wang,J. Pharm. Miomed. Anal 34 (2004) 1117-1124.
39. M. Clemons,R. E. Coleman,S. Verma,Cancer Treat. Rev. 30 (2004) 325-332
40. G. A. R. Johnston,Curr. Top. Med. Chem. 2 (2002) 903-913.
41. P. R. Latthe,V. A. Sunagar,B. V. Badami,J. Heterocyclic Chem 44 (2007) 1363-1371
42. D. S. Dodd,Z. Shen,T. Nishi,N. Graber,D. Bealls,M. Fong,T. Ebert,Bioorg. Med. Chem. Lett. 22 (6) (1996) 2693-2698
43. J. S. Roger,A. Asitha,C. Scot,L. John,A. Mohammed,H. K. Kashem,K. Josephine,A. Jennifer,S. S. Kowalski,T. Pullen,G. P. Roma,C. R. Roth,N. S. Sarko,M. P. Wilson,J. P. Winters,C. L. Wolak,Bioorg. Med. Chem. Lett. 17 (2007) 3660-3665
44. O. G. Ozden,E. Taner,G. Hakan,Y. Sulhiye,Bioorg. Med. Chem. Lett. 17 (2007) 2233-2236.