Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 11, 2007, Pages 3832-3841

  Radwan, Mohamed A A ^a   Ragab, Eman A ^b   Sabry, Nermien M ^a   El Shenawy, Siham M ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

1,3,4 Thiadiazoles; Anti inflammatory and tenidap; Indole; Thiophenes

Indexed keywords

2 (2 (1H BENZO[D]IMIDAZOL 2 YL)HYDRAZONO) 3 (1H INDOLE 3 YL) 3 OXOPRO PANENITRILE; 2 (2 (3 PHENYL 1H PYRAZOL 5 YL)HYDRAZONO) 3 (1H INDOLE 3 YL) 3 OXOPRO PANENITRILE; 2 (5 ACETYL 3 4 CHLOROPHENYL 1,3,4 THIADIAZOL 2(3H) LIDENE) 3 (1H INDOLE 3 YL) 3 OXOPROPANENITRILE; 2 (5 ACETYL 3 P TOLYL 1,3,4 THIADIAZOL 2(3H)LIDENE) 3 (1H INDOLE 3 YL) 3 OXOPROPA NENITRILE; 2 (5 ACETYL 3 PHENYL 1,3,4 THIADIAZOL 2(3H)LIDENE) 3 (1H INDOLE 3 YL) 3 OXOPROPA NENITRILE; 3 (1H INDOL 3 YL) 2 (3.5 DIPHENYL 1,3,4 THIADIAZOL 2(3H)LIDENE) 3 OXOPROPANE NITRILE; 3 (1H INDOLE 3 YL) 2 (4 OXO 3 PHENYLTHIAZOLIDIN 2 YLIDENE) 3 OXOPROPANENITRILE; 5 ACETYL 4 1H INDOL 3 YL) 2 (PHYNYLAMINO)THIOPHENE 3 CARBONITRILE; 5 BENZOYL 4 (1H INDOL 3 YL) 2 (PHYNYLAMINO)THIOPHENE 3 CARBONITRILE; ANALGESIC AGENT; ANTIINFECTIVE AGENT; ETHYL 5 (1 CYANO 2 (1H INDOL 3 YL) 2 OXOETHYLIDENE) 4,5 DIHYDRO 4 CHLOROPHENYL 1,3,4 THIADIAZOLE 2 CARBOXYLATE; ETHYL 5 (1 CYANO 2 (1H INDOL 3 YL) 2 OXOETHYLIDENE) 4,5 DIHYDRO 4 PHENYL 1,3,4 THIADIAZOLE 2 CARBOXYLATE; ETHYL 5 (1 CYANO 2 (1H INDOL 3 YL) 2 OXOETHYLIDENE) 4,5 DIHYDRO P TOLYL 1,3,4 THIADIAZOLE 2 CARBOXYLATE; INDOLE DERIVATIVE; INDOMETACIN; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; EDEMA; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; VISCERAL PAIN;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOLOGICAL ASSAY; INDOLES; MICE; PAIN MEASUREMENT; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34247351629     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.03.024     Document Type: Article

References (47)

1. Flower R.J., Moncada S., and Vane J.R. Goodman and Gilman's the Pharmacological Basis of Therapeutics. 7th ed. (1985), MacMillan, New York pp 695
2. Moore P.F., Larson D.L., Otterness I.G., Weissman A., Kadin S.B., Sweeney F.J., Eskara J.D., Nagahisa A., Sakakibara M., and Carty T.J. Inflamm. Res. 45 (1996) 54
3. Catry T.J., Showell H.J., Losee L.D., and Kadin S.B. Arthritis Rheum. 31 (1988) S89
4. McDonald B., Loose L., and Rosenwasser L. J. Arthritis Rheum. 31 (1988) S17
5. Moilanen E., Alanco J., Asmawi M.Z., and Vepaatalo H. Eicosanoids 7 (1988) 35
6. Wallace J.L. Can. J. Physiol. Pharmacol. 72 (1994) 1493
7. Mosti L., Menozzi G., Fossa P., Filippelli W., Gessi S., Rinaldi B., and Falcone G. Arzmeimittelforschung 50 (2000) 963
8. Schindler R., Hoefgen N., Heinecke K., Poppe H., and Szelenyi I. Pharmazie 55 (2000) 857
9. Misra U., Hitkari A., Saxena A.K., Gurtu S., and Shanker K. Eur. J. Med. Chem. 31 (1996) 629
10. Andreani A., Rambaldi M., Locatelli A., and Pifferi G. Eur. J. Med. Chem. 29 (1994) 903
11. Ebeid Mohamad Y., Lashine Sayed M., El-Adl Sobhy M., and Abou Kull Mansour E. Zagazig J. Pharm. Sci. 3 (1994) 40
12. El-Gendy Adel A., Abdou Naida A., Sarhan El-Taher Z., and El-Banna Hosny A. Alexandria J. Pharm. Sci. 7 (1993) 99
13. Kumar A., Saxena K.K., Gurtu S., Sinha J.N., and Shanker K. Indian Drugs 24 (1986) 1
14. Dandia A., Sehgal V., and Singh P. Indian J. Chem. 32B (1993) 1288
15. Sakemi S., and Sun H.H. J. Org. Chem. 56 (1991) 4304
16. Kawasaki Y., Yamashita M., and Otha S. J. Chem. Soc., Chem. Commun. (1994) 2085
17. Kawasaki Y., Yamashita M., and Otha S. Chem. Pharm. Bull. 44 (1996) 1831
18. Bartik K., Braekman J.C., Daloze D., Stoller C., Huysecom J., Vandevyver G., and Ottinger R. Can. J. Chem. 65 (1987) 2118
19. Tsuji S., Rinehart K.L., Gunasekera S.P., Kashman Y., Cross S.S., Lui M.S., Pomponi S.A., and Diaz M.C. J. Org. Chem. 53 (1988) 5446
20. Kawasaki Y., Katsuma H., Nakayama Y., Yamashita M., and Otha S. Heterocycles 48 (1998) 1887
21. Sun H.H., and Sakemi J. J. Org. Chem. 56 (1991) 4307
22. Vervoort H.C., Richards-Gross S.E., Fenical W., Lee A.Y., and Clardy J. J. Org. Chem. 62 (1997) 1486
23. Takahashi S., Matsunaga T., Hasegawa C., Saito H., Fujita D., Kiuchi F., and Tsuda Y. Chem. Pharm. Bull. 46 (1998) 1527
24. Verma M., Tripathi M., Saxena A.K., and Shanker K. Eur. J. Med. Chem. 29 (1994) 941
25. Bekhit A.A., Ashour H.M.A., and Guemei A.A. Arch. Pharm. 338 (2005) 167
26. Selvam C., Jachak S.M., Thilagavathi R., and Chakraborti A.K. Bioorg. Med. Chem. Lett. 15 (2005) 1793
27. Bekhit A.A., and Abdel-aziem T. Bioorg. Med. Chem. 12 (2004) 1935
28. Labanauskas L., Kalcas V., Udrenaite E., Gaidelis P., Brukstus A., and Dauksas V. Pharmazie 56 (2001) 617
29. Schenone S., Bruno O., Ranise A., Bondavalli F., Filippelli W., Falcone G., Giordano L., and Vitelli M.R. Bioorg. Med. Chem. 9 (2001) 2149
30. Mullican M.D., Wilson M.W., Conner D.T., Kostlan C.R., Schrier D.J., and Dyer R.D. J. Med. Chem. 36 (1993) 1090
31. Dogan H.N., Duran A., Rollas S., Sener G., Uysal M.K., and Gulen D. Bioorg. Med. Chem. 10 (2002) 2893
32. Ilies M.A., Masereel B., Rolin S., Scozzafava A., Campeanu G., Cimpeanu V., and Supuran C.T. Bioorg. Med. Chem. 12 (2004) 2717
33. Archana Srivastava V.K., and Kumar A. Eur. J. Med. Chem. 37 (2002) 873
34. Radwan M.A.A., and El-Sherbiny M. Bioorg. Med. Chem 15 (2007) 1206
35. Slatt J., Romero I., and Bergman J. Synthesis (2004) 2760
36. Dieckmann W., and Platz O. Chem. Ber. 38 (1906) 2989
37. Hegarty A.F., Cashoman M.P., and Scoti F.L. Chem. Commun. 13 (1971) 884
38. Wolkoff P. Can. J. Chem. 53 (1975) 1333
39. Cowper R.M., and Davidson L.H. Org. Syn., Coll. II (1943) 840
40. Winter C.A., Risley E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544
41. Obukowicz M.G., Welsch D.J., Salsgiver W.J., Martin-Berger, Chinn K.S., and Duffin K.L. J. Pharmacol. Exp. Ther. 287 (1998) 157
42. Koster R., Anderson M., and De Beer E.J. Fed. Proc. 18 (1959) 412
43. Collier H.D.J., Dinnin L.C., Johnson C.A., and Schneider C. Br. J. Pharmacol. 32 (1968) 295
44. Eddy N.B., and Leimback D. J. Pharmacol. Exp. Ther. 107 (1953) 385
45. Rani P., Srivastava V.K., and Kumar A. Eur. J. Med. Chem. 39 (2004) 449-452
46. Paget G.E., and Barnes J.M. Evaluation of Drug Activities Pharmacometics (1964), Academic Press, London and New York 1-135
47. Souza S.M., Aquino L.C., Bandeira M.A., Nobre M.E., and Viana G.S. Phytother. Res. 21 (2007) 220