Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5006-5011

  Kadi, Adnan A ^a   Al Abdullah, Ebtehal S ^a   Shehata, Ihsan A ^a   Habib, Elsayed E ^b   Ibrahim, Tarek M ^b   El Emam, Ali A ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b MANSOURA UNIVERSITY   (Egypt)

Author keywords

1,3,4 Thiadiazoles; 1 Adamantyl derivatives; Anti inflammatory activity; Antimicrobial activity

Indexed keywords

1,3,4 THIADIAZOLE DERIVATIVE; 2 [5 (1 ADAMANTYL) 2 THIOXO 1,3,4 THIADIAZOLIN 3 YL]ACETIC ACID; 2 [5 (1 ADAMANTYL) 2 THIOXO 1,3,4 THIADIAZOLIN 3 YL]PROPIONIC ACID; 3 [5 (1 ADAMANTYL) 2 THIOXO 1,3,4 THIADIAZOLIN 3 YL]PROPIONIC ACID; 5 (1 ADAMANTYL) 1,3,4 THIADIAZOLINE 2 ONE; 5 (1 ADAMANTYL) 1,3,4 THIADIAZOLINE 2 THIONE; AMPICILLIN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; GENTAMICIN; INDOMETACIN; N [5 (1 ADAMANTYL) 1,3,4 THIADIAZOL 2 YL] N' ARYLTHIOUREAS; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL GROWTH; BACTERIUM CULTURE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGUS CULTURE; FUNGUS GROWTH; GROWTH INHIBITION; IN VITRO STUDY; MALE; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PAW EDEMA; PSEUDOMONAS AERUGINOSA; RAT; STAPHYLOCOCCUS AUREUS;

ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; BACTERIA; CANDIDA ALBICANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; THIADIAZOLES;

EID: 77957838934     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.007     Document Type: Article

References (34)

1. I. Stylianakis, A. Kolocouris, N. Kolocouris, G. Fytas, G.B. Foscolos, E. Padalko, J. Neyts, and E. De Clerq Bioorg. Med. Chem. Lett. 13 2003 1699 1703
2. V.G. Vernier, J.B. Harmon, J.M. Stump, T.E. Lynes, and J.P. Marvel Toxicol. Appl. Pharmacol. 15 1969 642 665
3. S. Rabinovich, J.T. Baldini, and R. Bannister Am. J. Med. Sci. 256 1969 328 335
4. N. Kolocouris, G.B. Foscolos, A. Kolocouris, P. Marakos, N. Pouli, G. Fytas, S. Ikeda, and E. De Clercq J. Med. Chem 37 1994 2896 2902
5. J. Balzarini, B. Orzeszko, J.K. Mauri, and A. Orzeszko Eur. J. Med. Chem. 42 2007 993 1003
6. A.A. El-Emam, O.A. Al-Deeb, M.A. Al-Omar, and J. Lehmann Bioorg. Med. Chem. 12 2004 5107 5113
7. M.E. Burstein, A.V. Serbin, T.V. Khakhulina, I.V. Alymova, L.L. Stotskaya, O.P. Bogdan, E.E. Manukchina, V.V. Jdanov, and N.K. Sharova Antiviral. Res. 41 1999 135 144
8. K. Van Derpoorten, J. Balzarini, E. De Clercq, and J.H. Poupaert Biomed. Pharmacother. 51 1997 464 468
9. M.A. Abou-Gharbia, W.E. Childers, H. Fletcher, G. McGaughey, U. Patel, M.B. Webb, J. Yardley, T. Andree, C. Boast, R.J. Kucharik, K. Marquis, H. Morris, R. Scerni, J.A. Moyer, and J. Med Chembiochem 42 1999 5077 5094
10. J. Skolimowski, A. Kochman, L. Gbicka, and D. Metodiewa Bioorg. Med. Chem. 11 2003 3529 3539
11. J.C.E. Owen, and P.S. Whitton Brain. Res. 1117 2006 206 212
12. M.A. Al-Omar, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim, and A.A. El-Emam Molecules 15 2010 2526 2550
13. O.A. Al-Deeb, M.A. Al-Omar, N.R. El-Brollosy, E.E. Habib, T.M. Ibrahim, and A.A. El-Emam Arzneim-Forsch./Drug Res. 56 2006 40 47
14. A.A. El-Emam Chin. Pharm. J. 42 1990 309 315
15. A.A. Kadi, N.R. El-Brollosy, O.A. Al-Deeb, E.E. Habib, T.M. Ibrahim, and A.A. El-Emam Eur. J. Med. Chem. 42 2007 235 242
16. A.A. El-Emam, and T.M. Ibrahim Arzneim-Forsch./Drug Res. 41 1991 1260 1264
17. E. Antoniadou-Vyza, N. Avramidis, A. Kourounakis, and L. Hadjipetrou Arch. Pharm. 331 1999 72 78
18. A. Baxter, J. Bent, K. Bowers, M. Braddock, S. Brough, M. Fagura, M. Lawson, T. McInally, M. Mortimore, M. Robertson, R. Weaver, and B. Webborn Bioorg. Med. Chem. Lett. 13 2003 4047 4050
19. A. Foroumadi, S. Mansouri, Z. Kiani, and A. Rahmani Eur. J. Med. Chem. 38 2003 851 854
20. L.M. Thomasco, R.C. Gadwood, E.A. Weaver, J.M. Ochoada, C.W. Ford, G.E. Zurenko, J.C. Hamel, D. Stapert, J.K. Moerman, R.D. Schaadt, and B.H. Yagi Bioorg. Med. Chem. Lett. 13 2003 4193 4196
21. S. Karaku, and S. Rollas Il Farmaco 57 2002 577 581
22. H.N. Dogan, A. Duran, S. Rollas, G. Sener, M.K. Uysal, and D. Gülen Bioorg. Med. Chem. 10 2002 2893 2898
23. M.G. Mamolo, L. Vio, and E. Banfi Il Farmaco 51 1996 71 74
24. S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano, and G. Falcone Bioorg. Med. Chem. 14 2006 1698 1705
25. M. Santagati, M. Modica, A. Santagati, F. Russo, and M. Amico-Roxas Pharmazie 49 1994 880 884
26. E. Palaska, G. Sahin, P. Kelecin, N.T. Durlu, and G. Altinok Il Farmaco 57 2002 101 107
27. T.Y. Shen, and C.A. Winter A.B. Simmons, Advances in Drug Research 1977 Academic Press New York
28. E.S. Al-Abdullah, I.A. Shehata, O.A. Al-Deeb, and A.A. El-El-Emam Heterocycles 71 2007 379 388
29. A.A. El-Emam, and J. Lehmann Monatsh. Chem. 125 1994 587 591
30. P.R. Murray, E.J. Baron, M.A. Pfaller, F.C. Tenover, and R.H. Yolken G.L. Wood, J.A. Washington, Manual of Clinical Microbiology 1995 Am. Soc. Microbiol. Washington DC.
31. National Committee for Clinical Laboratory Standards (NCCLS), Approved standard document M-7A, Villanova, PA; 1985.
32. C.A. Winter, E.A. Risely, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544 547
33. D. Roche, D. Carniato, C. Leriche, F. Lepifre, S. Christmann-Franck, U. Graedler, C. Charon, S. Bozec, L. Doare, F. Schmidlin, M. Lecomte, and E. Valeur Discovery and structure-activity relationships of pentanedioic acid diamides as potent inhibitors of 11β-hydroxysteroid dehydrogenase type I Bioorg. Med. Chem. Lett. 19 2009 2674 2678
34. K.E. Chapman, A.E. Coutinho, M. Gray, J.S. Gilmour, J.S. Savill, and J.R. Seckl The role and regulation of 11β-hydroxysteroid dehydrogenase type 1 in the inflammatory response Mol. Cell. Endocrinol. 301 2009 123 131