Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

European Journal of Medicinal Chemistry

Volumn 45, Issue 4, 2010, Pages 1485-1493

  Hafez, Hend N ^a   El Gazzar, Abdel Rahman B A ^a   Nawwar, Galal A M ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Analgesic activities; Anti inflammatory; N Amino 2 thioxo thieno 2,3 d pyrimidin 4 one; S Glycosido thieno 2,3 d pyramidine

Indexed keywords

3 AMINO 5 METHYL 6 ETHYL[2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE]CARBOXLIC ACID; 3 AMINO 5 METHYL 6 ETHYL[2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE]CARBOXLIC ACID; 3 AMINO 5 METHYL 6 ETHYL[2 (2',3',5' TRI O ACETYL BETA DEXTRO ARABINOFURANOSYLTHIO)THIENO[2,3 D]PYRIMIDINE 4 ONE]CARBOXYLIC ACID; 3 AMINO 6 ACETYL 5 METHYL 2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 (2',3',5' TRI O ACETYL BETA DEXTRO ARABINOFURANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 (BETA DEXTRO ARABINOFURANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 (BETA DEXTRO GALACTOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 (BETA DEXTRO GLUCOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ACETYL 5 METHYL 2 THIOXOTHIENO[2,3 D]PYRIMIDIN 4 ONE; 3 AMINO 6 ETHYL(5 METHYL 2 THIOXOTHIENO[2,3 D]PYRIMIDIN 4 ONE)CARBOXYLIC ACID; 3 AMINO 6 ETHYL[5 METHYL 2 (BETA DEXTRO ARABINOFURANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE]CARBOXYLIC ACID; 3 AMINO 6 ETHYL[5 METHYL 2 (BETA DEXTRO GALACTOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE]CARBOXYLIC ACID; 3 AMINO 6 ETHYL[5 METHYL 2 (BETA DEXTRO GLUCOPYRANOSYLTHIO)THIENO[2,3 D]PYRIMIDIN 4 ONE]CARBOXYLIC ACID; ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; BROMIDE; CARRAGEENAN; INDOMETACIN; NUCLEOSIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DEACETYLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; MALE; MOUSE; NONHUMAN; PAIN; PAW EDEMA;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; PYRIMIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 77349104281     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.12.056     Document Type: Article

References (47)

1. Wolfe M.M., Lichtenstein D.R., and Singh G. N. Engl. J. Med. 340 (1999) 1888-1899
2. Dannhardt G., and Kiefer W. Eur. J. Med. Chem. 36 (2001) 109-126
3. Kiefer W., and Dannhardt G. Expert Rev. Clin. Immunol. 1 (2005) 431-442
4. Burnier M. Expert Opin. Drug Saf. 4 (2005) 491-499
5. Wong D., Wang M., Cheng Y., and FitzGerald G.A. Curr. Opin. Pharmacol. 5 (2005) 204-210
6. Rudic R.D., Brinster D., Cheng Y., Fries S., Song W.L., Austin S., Coffman T.M., and Fitz Gerald G.A. Circ. Res. 96 (2005) 1240-1247
7. Nussler A.K., and Billiar T.R.J. J. Leukoc. Biol. 54 (1993) 171-178
8. Ohshima H., and Bartsch H. Mutat. Res. 305 (1994) 253-264
9. Cochran F.R., Selph J., and Sherman P. Med. Res. Rev. 16 (1996) 547-563
10. El-Gazzar A.B.A., Hussein H.A.R., and Hafez H.N. Acta Pharm. 57 (2007) 395-411
11. El-Gazzar A.B.A., Hussien H.A.R., and Aly A.S. Phosphorus, Sulfur and Silicon 182 (2007) 35-56
12. El-Gazzar A.B.A., Hussien H.A., and Aly A.S. Phosphorus, Sulfur and Silicon 181 (2006) 2771-2784
13. El-Gazzar A.B.A. Phosphorus, Sulfur and Silicon 180 (2005) 283-293
14. El-Gazzar A.B.A., Abu-Zied Kh.M., and Khir El-Din N. Heteroat. Chem. 18 (2007) 34-43
15. El-Gazzar A.B.A., Gaafar A.M., Hafez H.N., and Abdel-Fattah A.M. Phosphorus, Sulfur and Silicon 182 (2007) 369-403
16. El-Gazzar A.B.A., Gaafar A.M., Youssif M.M.Y., Abu-Hashem A.A., and Badria F.A. Phosphorus, Sulfur and Silicon 182 (2007) 2009-2037
17. El-Gazzar A.B.A., Aly A.S., Zaki M.E.A., and Hafez H.N. Phosphorus, Sulfur and Silicon 183 (2008) 2119-2138
18. El-Gazzar A.B.A., Youssef M.M., Youssef A.M.S., Abu-Hashem A.A., and Badria F.A. Eur. J. Med. Chem. 44 (2009) 609-624
19. El-Gazzar A.B.A., Hafez H.N., Abu-Hashem A.A., and Aly A.S. Phosphorus, Sulfur and Silicon 184 (2009) 379-405
20. El-Gazzar A.B.A., El-Enany M.M., and Mahmoud M.N. Bioorg. Med. Chem. 16 (2008) 3261-3273
21. El-Gazzar A.B.A., and Hafez H.N. Acta Chim. Slov. 55 (2008) 359-371
22. El-Gazzar A.B.A., Hafez H.N., and Nawwar G.A.M. Eur. J. Med. Chem. 44 (2009) 1427-1436
23. Hafez H.N., Abbas H.A.S., and El-Gazzar A.B.A. Acta Pharm. 58 (2008) 359-378
24. Ram V.J., Haque N., and Shoeb A. J. PraKtische 334 (2004) 190
25. Caldwell W.T., and Sayin A.N. J. Am. Chem. Soc. 74 (1952) 4314-4317
26. Kwee M.S.L., and Stolk L.M.L. Pharm. Weekbl. Sci. 6 (1984) 101-104
27. Mitsuya H., Weinhold K.J., Furman P.A., St Clair M.H., Lehrman S.N., Gallo R.C., Bolognesi D., Barry D.W., and Broder S. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 7096-7100
28. Al Safarjalani O.N., Zhou X.J., Ras R.H., Shi J., Schinazi R.F., Naguib F.N., and El Kouni M.H. Cancer Chemother. Pharmacol. 55 (2005) 541-551
29. Attia A.M., Elgemeie G.H., and Shahada L.A. Tetrahedron 53 (1997) 17441-17448
30. Rashad A.E., Heikal O.A., El-Nazhawy A.O.H., and Abdel-Megeid F.M.E. Heteroat. Chem. 16 (2005) 226-234
31. Abdel-Megeid F.M.E., Hassan N.A., Zahran M.A., and Rashad A.E. Sulfur Lett. 21 (1998) 269-284
32. Perigaud C., Gosselin G., and Imbach J.-L. Nucleosides Nucleotides 11 (1992) 903-945
33. El-Gazzar A.B.A., Gaafar A.E.M., Hafez H.N., and Aly A.S. Phosphorus, Sulfur and Silicon 181 (2006) 1859-1893
34. Hafez H.N., and El-Gazzar A.B.A. Bioorg. Med. Chem. Lett. 18 (2008) 5222-5227
35. Ochoa C., Rodriguez J., Lopez Garcia M.L., Martinez A.R., and Martinez-Grueiro M. Arzneim. Forsch. 46 (1996) 643-648
36. Martins Alho M.A., D'Accors N.B., Ochoa C., Castro A., Calderon F., Chana A., Reviriego F., Paez J.A., Campillo N.A., Grueiro M.M., Cruz A.M.L.S., and Martinez A.R. Bioorg. Med. Chem. 12 (2004) 4431-4437
37. Seela F., and Peng X. J. Org. Chem. 71 (2006) 81-90
38. Harry-O'kuru R.E., Smith J.M., and Wolfe M.S. J. Org. Chem. 62 (1997) 1754-1759
39. Porcari A.R., and Townsend L.B. Nucleosides Nucleotides 18 (1999) 153-159
40. Okun R., Liddon S.C., and Lasagnal L. J. Pharmacol. Exp. Ther. 139 (1963) 107-114
41. Yesilada E., and Küpeli E. J. Ethnopharmacol. 79 (2002) 237-249
42. Tsurumi K., Kyuki K., Niwa M., Kokuba S., and Fujimura H. Arzneim. Forsch./Drug Res. 36 (1986) 1796-1800
43. Gavalas A., Kourounakis L., Litina D., and Kourounakis P. Arzneim. Forsch./Drug Res. 41 (1991) 423-426
44. Kidwai M., and Mishra A.D. Bull. Korean Chem. Soc. 24 (2003) 1038-1040
45. Gewald A.K., Schinke E., and Bottcher H. Chem. Ber. 99 (1966) 94-100
46. In: Olfert E.D., Cross B.M., and Mc William A.A. (Eds). Guide to the Care and Use of Experimental Animals. second ed. vol. 1 (1993), Canadian Council on Animal Care, Ontario, Canada 211
47. Kasahara Y., Hikino H., Tsurufuji S., Watanabe M., and Ohuchi K. Planta Med. 51 (1985) 325-331