Synthesis of novel 8-Hydroxy quinolin based 1,3,4-oxadiazoles and S-substituted 1,2,4-triazole derivatives and evaluation of their anti-inflammatory, analgesic, ulcerogenic and anti-microbial activities

Medicinal Chemistry

Volumn 7, Issue 6, 2011, Pages 663-673

  Alam, Mohammad Mahboob ^a   Shaharyar, Mohammad ^a   Hamid, Hinna ^a   Nazreen, Syed ^a   Haider, Saqlain ^a   Alam, Mohammad Sarwar ^a  

^a HAMDARD UNIVERSITY   (India)

Author keywords

1,3,4 Oxadiazole derivatives; Analgesic; Animicrobial; Anti inflammatory activity; S substituted phenacyl 1,2,4 Triazole derivatives; Ulcerogenic

Indexed keywords

2 [4 (3 CHLOROPHENYL) 5 [(QUINOLIN 8 YLOXY)METHYL] 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [4 (3 CHLOROPHENYL) 5 [(QUINOLIN 8 YLOXY)METHYL] 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 HYDROXYPHENYL)ETHANONE; 2 [4 (4 CHLOROPHENYL) 5 [(QUINOLIN 8 YLOXY)METHYL] 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 2 [4 (4 METHOXYPHENYL) 5 [(QUINOLIN 8 YLOXY)METHYL] 4H 1,2,4 TRIAZOL 3 YLTHIO] 1 (4 BROMOPHENYL)ETHANONE; 8 [[5 [(2,4 DICHLOROPHENOXY)METHYL] 1,3,4 OXADIAZOL 2 YL]METHOXY]QUINOLINE; AMPICILLIN; FLUCONAZOLE; INDOMETACIN; OXADIAZOLE DERIVATIVE; QUINOLINE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; RAT; ULCEROGENESIS;

EID: 80755143189     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340611797928334     Document Type: Article

References (45)

1. Ghorab, M.M.; El-Sharief, A.M. Sh.; Ammolar, Y.A.; Mohamed, Sh. I. Synthesis and Antifungal activity of some new miscellaneous S-triazoles. Phosphorous, Sulfur and Silicon., 2001, 173, 223-233. (Pubitemid 33392099)
2. Zhongyi, W.; Haoxin, S.; Haijian, S. Synthesis of Chiral Fused Heterocyclic Compounds containing 1,2,4-Triazole Ring. J. Heterocycl. Chem., 2001, 38, 355-357.
3. Patel, N.B.; Khan, I.H.; Rajani, S.D. Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles. Eur. J. Med. Chem., 2010, 45, 4293-4299.
4. Labanauskas, L.; Kalcas, V.; Udrenaite, E.; Gaidelis, P.; Brukstus, A.; Dauksas, V. Synthesis of 3-(3,4-Dimethoxyphenyl)-1H-1,2,4-triazole-5-thiol and 2-Amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole derivatives exhibiting antiinflammatory activity. Pharmazie, 2001, 56, 617-619. (Pubitemid 32751849)
5. Foroumadi, A.; Mirzaei, M.; Shafiee, A. Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives. Pharmazie, 2001, 56, 610-612. (Pubitemid 32751847)
6. Chang, H.L.; In Cho, H.; Lee, K. J. Synthesis of 1,3,4-oxadiazoles having phenol or thiophenol group. Bull. Korean Chem. Soc., 2001, 22, 1153-1155 and references cited therein. (Pubitemid 33358504)
7. Shawa, A.Y.; Chang, C.; Hsu, M.; Lu, P.; Yang, C.; Chen, H.; Lo, C.; Shiau, C.; Chern, M. Synthesis and structure-activity relationship study of 8-hydroxyquinoline-derived Mannich bases as anticancer agents. Eur. J. Med. Chem., 2010, 45, 2860-2867.
8. Kaplancikli, Z. A.; Turan-Zitouni, G.; Ozdemir, A.; Revial, G. New triazole and triazolothiadiazine derivatives as possible antimicrobial agents. Eur. J. Med. Chem., 2008, 43, 155-159.
9. Zamani, K.; Faghihi, K.; Sangi, M.R.; Zolgharnein, J. Synthesis of some new substituted 1,2,4-triazole and 1,3,4-thiadiazole and their derivatives. Turk. J. Chem., 2003, 27, 119-125. (Pubitemid 36315005)
10. Umut, S.G.; Nesrin, G.K.; Ozgur, G.; Yavuz, K.; Ekrem, K.; Samil I.; Goknur, A.; Meral, O. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-antiinflammatory and antimicrobial activities. Bioorg. Med. Chem., 2007, 15, 5738-5751.
11. Kadi, A.A.; El-Brollosy, N.R.; Al-Deeb, O.A.; Habib, E.E.; Tarek, I.M.; El-Emam, A.A. Synthesis, antimicrobial, and antiinflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5- substituted-1,3,4-thiadiazoles. Eur. J. Med. Chem., 2007, 42, 235-242.
12. Navidpour, L.; Shafaroodi, H.; Abdi, K.; Amini, M.; Ghahremani, M.H.; Dehpour, A.R; Shafiee, A. Design, Synthesis and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors. Bioorg. Med. Chem., 2006, 14, 2507-2517. (Pubitemid 43343637)
13. Bayrak, H.; Demirbas, A.; Karaoglu, S.A.; Demirbas, N. Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur. J. Med. Chem., 2009, 44, 1057-1066.
14. Labanauskas, L.; Udrenaite, E.; Gaidelis, P.; Bruktus, A. Synthesis of 5-(2,3,4-methoxy-phenyl)-4H-1,2,4-triazole-3-thiol derivatives exhibiting anti-inflammatory activity. Il Farmaco, 2004, 59, 255-259. (Pubitemid 38471918)
15. Güzeldemirci, N.U.; Ömer, K. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem., 2010, 45, 63-68.
16. Eswaran, S.; Adhikari, A.V.; Suchetha, S.N. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur. J. Med. Chem., 2009, 44, 4637-4647.
17. Demirbas, A.; Sahin, D.; Demirbas, N.; Karaoglu, S. A. 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., 2009, 44, 2896-2903.
18. Virginija, J.; Burbulien, M.M.; Mekuskien, G.; Emilija, U.; Gaidelis, P.; Povilas, V. Synthesis and antiinflammatory activity of 5-(6-methyl-2- substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives. Il Farmaco, 2003, 58, 323-328. (Pubitemid 36513581)
19. Holla, B.S.; Poorjary, N.K.; Rao, S.B.; Shivananda, M.K. New bisaminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur. J. Med. Chem., 2002, 37, 511-517. (Pubitemid 35245174)
20. Bozdogan, B.ü.; Esel, D.; Whitener, C.; Browne, F.A.; Appelbaum, P.C. Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center. Journal of Antimicrobial Chemotherapy., 2003, 52, 864.
21. Khan, M.W.; Alam, M.J.; Rashid, M.A.; Chowdhury, R. A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg. Med. Chem., 2005, 13, 4796-4805. (Pubitemid 40943504)
22. Fukai, T.; Oku, Y.; Hano, Y.; Terada, S. Antimicrobial activities of hydrophobic 2-Arylbenzofurans and an Isoflavone against Vancomycin-Resistant Enterococci and Methicillin-Resistant Staphylococcus aureus, Planta Med., 2004, 70, 685-687. (Pubitemid 39013186)
23. Jang, J. H.; Kanoh, K.; Adachi, K.; Shizuri, Y. New dihydrobenzofuran derivative, awajanoran, from marine-derived Acremonium sp. AWA16-1, J. Antibiot., 2006, 59, 428-431. (Pubitemid 44433248)
24. Rida, S.M.; El-Hawashi, S.A.; Fahmy, H.T.; Hazza, A.A.; El-Meligy, M.M. Synthesis, antimicrobial activity, pharmacophore analysis of some new 2-(substitutedphenyl /benzyl)-5-[(2-benzofuryl)carboxamido]benzoxazoles, Arch. Pharm. Res., 2006, 29, 16-25.
25. Rida, S.M.; El-Hawashi, S.A.; Fahmy, H.T.; Hazza, A.A.; El-Meligy, M.M. Synthesis of Novel Benzofuran and Related Benzimidazole Derivatives for Evaluation of In Vitro Anti-HIV-1, Anticancer and Antimicrobial Activities, Arch. Pharm. Res., 2006, 29, 826-833. (Pubitemid 44808446)
26. Fukai, T.; Kaitou, K.; Terada, S. Antimicrobial activity of 2-arylbenzofurans from Morus species against methicillin-resistant Staphylococcus aureus, Fitoterapia., 2005, 76, 708-711. (Pubitemid 41688394)
27. Guinea, J.; Sanchez-Somolinos, M.; Cuevas, O.; Pelaez, T.; Bouza, E. Fluconazole resistance mechanisms in Candida krusei: The contribution of efflux-pumps, Med. Mycol., 2006, 44, 575-578. (Pubitemid 44377568)
28. Hakki, M.; Staab, J.F.; Marr, K.A. Emergence of a Candida krusei isolate with reduced susceptibility to caspofungin during therapy, Antimicrob. Agents Chemother., 2006, 50, 2522-2524. (Pubitemid 43993195)
29. Olver, W. J.; Scott, F.; Shankland, G.S. Successful treatment of Candida krusei fungemia with amphotericin B and caspofungin, Med. Mycol ., 2006, 44, 655-657. (Pubitemid 44650517)
30. Tammolara, V.K.; Narurkar, M.M.; Crider, A.M.; Khan, M.A. Morpholinoalkyl ester prodrugs of diclofenac: Synthesis, in vitro and in vivo evaluation. J. Pharm. Sci., 1994, 83, 644-648. (Pubitemid 24219812)
31. For review: (a) Sondhi, S. M.; Singhal, N.; Johar, M.; Reddy, B. S.N.; Lown, J. W. Curr. Med. Chem., 2002, 9, 1045;
32. Sondhi, S. M.; Rajvanshi, S.; Singh, N.; Jain, S.; Lahoti, A. M. Cent. Eur. J. Chem., 2004, 2, 141.
33. Bhandari, S.V.; Bothara, K.G.;. Raut, M.K.; Patil, A.A.; Sarkate, A.P.; Mokale, V.J. Design, Synthesis and Evaluation of Antiinflammatory, Analgesic and Ulcerogenicity studies of Novel SSubstituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of Diclofenac acid as Nonulcerogenic Derivatives. Bioorg. Med. Chem., 2008, 16, 1822-1831. (Pubitemid 351233042)
34. Sahin, G.; Palaska, E.; Ekizoglu, M.; Meral, O. Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives. Il Farmaco, 2002, 57, 539-542. (Pubitemid 34765743)
35. Jayashankar.; Lokanath Rai, K.M.; Baskaran, N.; Sathish, H.S. Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as antiinflammatory and analgesic agents. Eur. J. Med. Chem., 2009, 44, 3898-902.
36. Sharma , J.; Husain, S.; Amir, M. Synthesis and Study of Some Newer Analogues of Quinolin-8-ol as Potent Antimicrobial Agents. E-Journal of Chem., 2008, 5, 1008-1014.
37. Winter, C.A.; Risley, E.A.; Nuss, G.W. Carrageenin-induced oedema in hind paws of the rat as an assay for antiinflammatory drugs. Proc. Soc. Exp. Biol. Med., 1962, 111, 544-547.
38. Kar, D.M.; Sahu, S.K.; Misro, P.K. Pharmacological activities of 1-Acetyl-3 (3-Methylanilino-2-Hydroxypropyl Oximino) Indole-2, 3-Dione. Indian drug., 2003, 40, 261-266.
39. Motilva, V.; Illanes, M.; Lacave, M.I.; Fidalgo, S. S. Angiogenesis, cell proliferation and apoptosis in gastric ulcer healing. Effect of a selective cox-2 inhibitor. Eur. J. Med. Chem., 2004, 505, 187-194. (Pubitemid 39535691)
40. Omar, F.A.; Mahfouz, N.M.; Rahman, M.A. Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives. Eur. J. Med. Chem., 1996, 31, 819-825. (Pubitemid 26341447)
41. Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N.; Altinok, G. Synthesis and antiinflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Il Farmaco., 2002, 57, 101-107. (Pubitemid 34175107)
42. Perez, C.; Pauli, M.; Bazerque, P. An antibiotic assay by the well agar method. Acta Biol. Med. Exp., 1990, 15, 113-115.
43. Demirbas, N.; Alpay-Karao glu, S.; Demirbas, A.; Sancak, K. synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2yl) methyl-5-oxo-[1,2,4]triazole derivatives. Eur. J. Med. Chem., 2004, 39, 793-804.
44. Klimesova,V.; Zahajska, L.; Waisser, K.; Kaustova, J.; Mollmann, U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Il Farmaco, 2004, 59, 279-288. (Pubitemid 38471921)
45. Pomarnacka, E.; Kornicka, A. Synthesis and in vitro anticancer and anti-HIV evaluation of new 2-mercaptobenzenesulfonamides. Il Farmaco, 2001, 56, 571-577. (Pubitemid 32727928)