Synthesis of some new S-alkylated 1,2,4-triazoles, their Mannich bases and their biological activities

Archiv der Pharmazie

Volumn 345, Issue 3, 2012, Pages 203-214

  Alam, Mohammad Mahboob ^a   Nazreen, Syed ^a   Haider, Saqlain ^a   Shafi, Syed ^a   Yar, Mohammad Shahar ^b   Hamid, Hinna ^a   Alam, Mohammad Sarwar ^a  

^a HAMDARD UNIVERSITY   (India)

^b HAMDARD UNIVERSITY   (India)

Author keywords

Analgesic; Anti inflammatory; Antimicrobial activity; Mannich base; Triazole; Ulcerogenic

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 2 [5 [(4 BIPHENYLOXY)METHYL) 4 (4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 CHLOROPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 METHOXYPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 NITROPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 CHLOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (PHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 FLUOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 FLUOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 METHOXYPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 METHOXYPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 METHOXYPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (PHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 NITROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (PHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (4 NITROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO]1 (4 PHENYLPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (PHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [5 [(4 BIPHENYLOXY)METHYL] 4 (PHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 NITROPHENYL)ETHANONE; 2 [5 [(4 PHENYLPHENOXY)METHYL] 4 (4 FLUOROPHENYL) 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (PHENYL)ETHANONE; 3 (4 NITROPHENYLETHYLTHIO) 5 [(4 BIPHENYLOXY)METHYL] 4 PHENYL 4H 1,2,4 TRIAZOLE; 3 (4 NITROPHENYLMETHYLTHIO) 5[(4 BIPHENYLOXY)METHYL] 4 (4 FLUOROPHENYL) 4H 1,2,4 TRIAZOLE; 3 (PHENYLETHYLTHIO 5 [(4 BIPHENYLOXY)METHYL] 4 (4 FLUOROPHENYL) 4H 1,2,4 TRIAZOLE; 3 (PHENYLETHYLTHIO) 5 [(4 BIPHENYLOXY)METHYL] 4 PHENYL 4H 1,2,4 TRIAZOLE; 5 [(4 BIPHENYLOXY)METHYL] 4 (2 METHYLPHENYL) 2 (MORPHOLINOMETHYL) 2H 1,2,4 TRIAZOLE 3(4H)THIONE; 5 [(4 BIPHENYLOXY)METHYL] 4 (4 CHLOROPHENYL) 2 (MORPHOLINOMETHYL) 2H 1,2,4 TRIAZOLE 3(4H)THIONE; 5 [(4 BIPHENYLOXY)METHYL] 4 (4 METHOXYPHENYL) 2 [(PYRROLIDIN 1 YL)METHYL] 2H 1,2,4 TRIAZOLE 3(4H)THIONE; 5 [(4 BIPHENYLOXY)METHYL] 4 (PHENYL) 2 (MORPHOLINOMETHYL) 2H 1,2,4 TRIAZOLE 3(4H)THIONE; 5 [(4 BIPHENYLOXY)METHYL](4 METHOXYPHENYL) 3 (N METHYL PIPERAZINE 4 YLMETHYLTHIO) 4H 1,2,4 TRIAZOLE; AMOXICILLIN; ANTIINFLAMMATORY AGENT; FLUCONAZOLE; IBUPROFEN; MANNICH BASE; UNCLASSIFIED DRUG;

ALKYLATION; ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS NIGER; BIOLOGICAL ACTIVITY; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; FEMALE; IN VITRO STUDY; KLEBSIELLA PNEUMONIAE; MALE; NONHUMAN; PAIN; PAW EDEMA; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; RAT; REACTION TIME; STAPHYLOCOCCUS AUREUS; STOMACH IRRITATION; STOMACH ULCER; STRUCTURE ACTIVITY RELATION;

ANALGESICS; ANIMALS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; DISEASE MODELS, ANIMAL; FEMALE; IBUPROFEN; MALE; MANNICH BASES; MICROBIAL SENSITIVITY TESTS; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84858039209     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201100128     Document Type: Article

References (31)

1. J. B. Polya, in Comprehensive Heterocyclic Chemistry, (Eds:, A. R. Katritzky, C. W. Rees, K. T. Potts,), Pergamon Press, Oxford 1984, 5, 733.
2. M. M. Ghorab, E. l-Sharief, Y. A. Ammar, S. I. Mohamed, Phosphorus, Sulfur & Silicon Relat. Elem. 2001, 173, 223-233.
3. W. Zhongyi, S. Haoxin, S. Haijian, J. Heterocycl. Chem. 2001, 38, 355-357.
4. E. Palaska, G. Sahin, P. Kelicen, N. T. Durlu, G. Altinok, Il Farmaco. 2002, 57, 101-107.
5. L. Labanauskas, V. Kalcas, E. Udrenaite, P. Gaidelis, A. Brukstus, V. Dauksas, Pharmazie. 2001, 56, 617-619.
6. T. Gulhan, Z. A. Kaplancikli, A. Ozdemir, P. Chevallet, H. B. Kandilci, B. Gumusel, Arch. Pharm. Chem. Life Sci. 2007, 340, 586-590.
7. S. Sharma, S. Ganga, R. Abdul, M. Zahin, Arch. Pharm. Chem. Life Sci. 2008, 341, 714-720.
8. X. Y. Sun, C. X. Wei, K. Y. Chai, H. R. Piao, Z. S. Quan, Arch. Pharm. Chem. Life Sci. 2008, 341, 288-293.
9. A. I. Alsarra, O. M. Ahmed, K. F. Alanazi, H. E. Tahir, M. A. Alsheikh, H. S. Neau, Int. J. Med. Sci. 2010, 7, 232-239.
10. G. R. Jorge, T. L. David, Geriat. Nephrol. Urol. 1997, 7, 51-57.
11. H. H. Tan, W. M. C. Ong, S. H. Lai, W. C. Chow, Sing. Med. J. 2007, 48, 582-585.
12. H. Bayrak, A. Demirbas, S. A. Karaoglu, N. Demirbas, Eur. J. Med. Chem. 2009, 44, 1057-1066.
13. K. Zamani, K. Faghihi, M. R. Sangi, J. Zolgharnein, Turk. J. Chem. 2003, 27, 119-125.
14. S. G. Umut, G. K. Nesrin, G. Ozgur, K. Yavuz, K. Ekrem, I. Samil, A. Goknur, O. Meral, Bioorg. Med. Chem. 2007, 15, 5738-5751.
15. A. A. Kadi, N. R. El-Brollosy, O. A. Al-Deeb, E. E. Habib, I. M. Tarek, A. A. El-Emam, Eur. J. Med. Chem. 2007, 42, 235-242.
16. L. Navidpour, H. Shafaroodi, K. Abdi, M. Amini, M. H. Ghahremani, A. R. Dehpour, A. Shafiee, Bioorg. Med. Chem. 2006, 14, 2507-2517.
17. G. Mazzone, F. Bonina, R. Arrigo-Reina, G. Blandino, Farmaco. Ed. Sci. 1981, 36, 181-196.
18. T. Somorai, G. Szilagyi, E. Bozo, G. Nagy, Hung. Teljes HU. 34457 A2 850328. 1986 [Chem. Abstr. 1986, 105, 97474].
19. G. Mekuskiene, P. Vainilavicius, P. Gaidelis, Pharmazie. 1998, 53, 94-96.
20. T. Gulhan, Z. A. Kaplancikli, A. Ozdemir, P. Chevallet, H. B. Kandilci, B. Gumusel, Arch. Pharm. Chem. Life Sci. 2007, 340, 586-590.
21. D. M. Springer, B. Y. Luh, J. J. Bronson, K. E. McElhone, M. M. Mansuri, K. R. Gregor, D. O. Nettleton, P. L. Stanley, K. M. Tramposch, Bioorg. Med. Chem. 2000, 8, 1087-1109.
22. P. K. Halen, K. K. Chagti, R. Giridhar, M. R. Yadav, Chem. Biol. Drug. Des. 2007, 70, 450-455.
23. M. R. Yadav, D. M. Brahamkshatriya, S. T. Shirude, A. Parmar, R. Balaraman, R. Giridhar, Bioorg. Med. Chem. 2006, 14, 8701-8706.
24. H. Kumar, S. A. Javed, S. A. Khan, M. Amir, Eur. J. Med. Chem. 2008, 43, 2688-2698.
25. S. F. Barbuceanu, G. L. Almajan, I. Saramet, C. Draghici, R. Socoteanu, F. Barbuceanu, J. Serb. Chem. Soc. 2009, 74, 1041-1049.
26. B. Jiang, Y. Zeng, M. J. Li, J. Y. Xu, Y. N. Zhang, Q. J. Wang, N. Y. Sun, T. Lu, X. M. Wu, Arch. Pharm. 2010, 343, 500-508.
27. S. V. Bhandari, K. G. Bothara, M. K. Raut, A. A. Patil, A. P. Sarkate, V. J. Mokale, Bioorg. Med. Chem. 2008, 16, 1822-1831.
28. C. A. Winter, E. A. Risley, G. W. Nuss, Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
29. S. H. Ferreira, J. Pharma. Pharmaco. 1979, 31, 648.
30. D. M. Kar, S. K. Sahu, P. K. Misro, Indian.Drug. 2003, 40, 261-266.
31. C. Perez, M. Pauli, P. Bazerque, Acta. Biol. Med. Exp. 1990, 15, 113-115.