DBU-assisted cyclorelease elimination: Combinatorial synthesis and γglutamyl cysteine synthetase and glutathione-S-transeferase modulatory effect of C-nucleoside analogs

Combinatorial Chemistry and High Throughput Screening

Volumn 6, Issue 1, 2003, Pages 37-50

  Mishra, R C ^a   Tewari, Neetu ^a   Arora, Kavita ^a   Ahmad, Rumana ^a   Tripathi, R P ^a   Tiwari, V K ^a   Walter, R D ^b   Srivastava, A K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b BERNHARD NOCHT INSTITUTE FOR TROPICAL MEDICINE   (Germany)

Author keywords

C nucleosides; Combinatorial synthesis; Cyclorelease elimination; Diazabicyclo (5.4.0) undec 7 ene; Dihydropyrimidinones; Glutathione S transeferase; glutamyl cysteine synthetase

Indexed keywords

1 (2 HYDROXYPHENYLMETHYL) 3 [(3 ACETYL)PHENYL 5,6 DIHYDRO 6 (1',2' O ISOPROPYLIDENE 3' O METHYL 1',4' TETRAHYDROFURANOS 4' YL)]PYRIMIDINE 2,4 DIONE; 1 (4 BROMOPHENYLMETHYL) 3 [3 (CYANO)PHENYL 5,6 DIHYDRO 6 (1',2' O ISOPROPYLIDENE 3' O METHYL 1',4' TETRAHYDROFURANOS 4' YL)]PYRIMIDINE 2,4 DIONE; 1 (FURYLMETHYL) 3 [4 BUTYLPHENYL 5,6 DIHYDRO 6 (1',2' O ISOPROPYLIDENE 3' O METHYL 1',4' TETRAHYDROFURANOS 4' YL)]PYRIMIDINE 2,4 DIONE; 1 [(4 BROMO)PHENYLMETHYL] 3 [BENZYL 5,6 DIHYDRO 6 (1',2' O ISOPROPYLIDENE 3' O BENZYL 1',4' TETRAHYDROFURANOS 4'YL)]PYRIMIDINE 2,4 DIONE; C NUCLEOSIDE; GLUTAMATE CYSTEINE LIGASE; GLUTATHIONE TRANSFERASE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEVELOPMENT; DRUG EFFECT; DRUG SYNTHESIS; ENZYME INHIBITION; FILARIA; PRIORITY JOURNAL;

FILARIA;

EID: 0037321177     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207033329887     Document Type: Article

References (35)

1. Gallop, M.A.; Barrot, R.W.; Dower, W.J.; Foder, S.P.; Gordon E.M. J Med. Chem. 1994, 37, 1233; Desai, M. C.; Zukkerman, A.N.; Moss, W.H. Drug Development Res. 1994, 33, 174; Terrett N.K. Tetrahedron 1994, 51, 8135.
2. Gallop, M.A.; Barrot, R.W.; Dower, W.J.; Foder, S.P.; Gordon E.M. J Med. Chem. 1994, 37, 1233; Desai, M. C.; Zukkerman, A.N.; Moss, W.H. Drug Development Res. 1994, 33, 174; Terrett N.K. Tetrahedron 1994, 51, 8135.
3. Gallop, M.A.; Barrot, R.W.; Dower, W.J.; Foder, S.P.; Gordon E.M. J Med. Chem. 1994, 37, 1233; Desai, M. C.; Zukkerman, A.N.; Moss, W.H. Drug Development Res. 1994, 33, 174; Terrett N.K. Tetrahedron 1994, 51, 8135.
4. Kobayashi, S. Chem. Soc. Rev. 1999, 28, 1.
5. Netzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev. 1997, 97, 97.
6. Siehe, Z.B.; Patek, M.B.; Drake, M.L. Tetrahedron Lett. 1994, 35, 9169.
7. Ottesen, E.A. Infectious diseases and public health, Angelico, M; Rochhi, G. Ed. Bolborn Publishers, 1988, pp 58-64.
8. Michael, E.; Bundy, D.A.P. Parasitology Today 1997, 13, 472.
9. J.; Robertson, A.P.; Bjorn, H. Parasitology 1997, 114, S111.
10. Firlamb, A.H.; Blockman, P.; Ulrich, P.; Chat, B.T.; Cerani, A. Science 1985, 227, 1285.
11. Secherling, C.; Krauch, Siegel, R.L. Top. Med. Parasitol. 1991, 42, 232.
12. Varki, A.; Glycobiology, 1993, 3, 97; Rademacher, T.W.; Parekh, R.B.; Dwek, R. A. Ann. Rev. Biochem. 1988, 57, 785.
13. Varki, A.; Glycobiology, 1993, 3, 97; Rademacher, T.W.; Parekh, R.B.; Dwek, R. A. Ann. Rev. Biochem. 1988, 57, 785.
14. Tripathi, R.P.; Singh, V.; Khan, A.R.; Bhaduri, A.P.; Bhatnagar, S.; Srivastava, A.K. Trends in carbohydrate chemistry edited by P.L. Soni, Surya International Publications, Dehradun India 1995, pp 1-4.
15. Srivastava, A.K.; Tripathi, R.P.; Khan, A.R.; Bhaduri, A.P. Helminthologia 1995, 32, 25.
16. Khan, A.R.; Tripathi, R.P.; Bhaduri, A.P.; Sahai, R.; Puri, A.; Tripathi, L.M.; Srivastava, V.M.L. Eur. J. Med. Chem. 2001, 36, 435.
17. Burchenal, J.H.; Ciovacco, K.; Kalhar, K.; Toole, T.O.; Kiefner, R.; Dowing, M.D.; Chu, C.K.; Watanabe, K.A.; Wempen, I.; Fox, J.J. Cancer Res. 1976, 36, 1520.
18. Schaeffer, H.J.; Beauchamp, L.; de Miranda, P.; Ellion, G.B.; Bour, D.J.; Collins, P. Nature 1978, 272, 583.
19. Robins, R.K.; Srivastava, P.C.; Narayanan, V.L.; Plowman, J.; Paul, K.D. J. Med. Chem. 1982, 25, 107.
20. Fischer, J.F.; Chance, M.L.; Hanboula, S.Y.; Monsigny, M.; Roche, A.C.; Mayer, R.M.; Hommel, M. Antimicrob. Agents. Chemother. 1992, 36, 2228.
21. Burchenal, J.H.; Ciovacco, K.; Kalhar, K.; Toole, T.O.; Kiefner, R.; Dowing, M.D.; Chu, C.K.; Watanabe, K.A.; Wempen, I.; Fox, J.J. Cancer Res. 1976, 36, 1520.
22. Tripathi, R.P.; Rastogi, S.K.; Kundu, B.; Saxena, J.K.; Reddy, V.J.M.; Srivastva, S.; Chandra, S.; Bhaduri, A.P. Combi. Chem. & Highthroughput Screening 2001, 4, 237.
23. Savoca, A. C. Encyclopedia of reagents for Organic synthesis Edit. Paquette, L. A. John Wiley & Sons, 1995.
24. Chu, C.K.; Wempen, I.; Chu, C.K.; Watanabe, K.A.; Fox, J.J. J. Org. Chem. 1976, 41, 2793.
25. Namne, A.; Gouyetti, C.; Fillion, M.P.; Fillion, G.; Huynh, D.J. J Med. Chem. 1992, 35, 3039. Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med. Chem. 1998, 41, 191; Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel, L.A.; Sudebeck, E.A.; Uckun, F.M. Bioorg. Med. Chem. Letters 1998, 8, 1461; Sudebeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel, L.A. Antimicrob. Agents Chemother. 1998, 42, 3225.
26. Namne, A.; Gouyetti, C.; Fillion, M.P.; Fillion, G.; Huynh, D.J. J Med. Chem. 1992, 35, 3039. Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med. Chem. 1998, 41, 191; Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel, L.A.; Sudebeck, E.A.; Uckun, F.M. Bioorg. Med. Chem. Letters 1998, 8, 1461; Sudebeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel, L.A. Antimicrob. Agents Chemother. 1998, 42, 3225.
27. Namne, A.; Gouyetti, C.; Fillion, M.P.; Fillion, G.; Huynh, D.J. J Med. Chem. 1992, 35, 3039. Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med. Chem. 1998, 41, 191; Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel, L.A.; Sudebeck, E.A.; Uckun, F.M. Bioorg. Med. Chem. Letters 1998, 8, 1461; Sudebeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel, L.A. Antimicrob. Agents Chemother. 1998, 42, 3225.
28. Namne, A.; Gouyetti, C.; Fillion, M.P.; Fillion, G.; Huynh, D.J. J Med. Chem. 1992, 35, 3039. Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med. Chem. 1998, 41, 191; Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel, L.A.; Sudebeck, E.A.; Uckun, F.M. Bioorg. Med. Chem. Letters 1998, 8, 1461; Sudebeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel, L.A. Antimicrob. Agents Chemother. 1998, 42, 3225.
29. Lowry, O.H.; Rosebrough, N.J.; Farr, A.L.; Randall, R. J. J. Biol. Chem. 1951, 193, 265-275.
30. Romero, M.J.M.; Canada, A.T. Toxicol. Appl. Pharmacol. 1991, 111, 485.
31. Huang, C.S.; Moore, W.R.; Meister, A. Proc. Natl. Acad. Sci. USA 1988, 85, 2464.
32. Brophy, P.M. The role of glutathione-S- transferase in cestodes, Ph.D. Thesis, University College of Wales, Aberystwyth, 1988.
33. Precious, W.Y.; Barret, J. The possible absence of cytochrome P-450 linked xenobiotic metabolism in heliminthes. Biochim. Biophys. Acta 1989, 992, 215-222.
34. Dubois, V.L.; Platel, D.F.; Pauly, G.; Tribouley, D. J. Plasmodium bergei: Implication of intracellular glutathione and its related enzymes in chloroquine resistance in vivo. Exp. Parasitology 1995, 81, 117-124.
35. Ketterer, B.; Clark, A.G. Soluble glutathione transferase isozymes. In glutathione conjugation: its mechanism and biological significance (Ed. Sies, H. and Keterer, B.) Academic press. London, 1989, pp 73-135.