Design of inhibitors against guanase: Synthesis and biochemical evaluation of analogues of azepinomycin

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 21, 2006, Pages 5551-5554

  Ujjinamatada, Ravi K ^a   Bhan, Anila ^a   Hosmane, Ramachandra S ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

Azepinomycin analogues; Biochemical studies; Guanase (guanine deaminase); Inhibitors; Synthesis

Indexed keywords

AZEPINOMYCIN; ENZYME INHIBITOR; GUANINE DEAMINASE; HYDROLASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BIOCHEMISTRY; CHEMICAL ANALYSIS; COMPETITIVE INHIBITION; CRYSTAL STRUCTURE; DEAMINATION; DRUG ACTIVITY; DRUG DESIGN; DRUG DETERMINATION; DRUG INHIBITION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SYNTHESIS; HYDROLYSIS KINETICS; STRUCTURE ANALYSIS;

ANIMALS; AZEPINES; GUANINE DEAMINASE; RABBITS;

EID: 33748763625     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.08.033     Document Type: Article

References (45)

1. Knights Jr. E.M., Whitehouse J.L., Hue A.C., and Santos C.L. J. Lab. Clin. Med. 65 (1965) 355
2. Nishikawa Y., Fukumoto K., Watanabe F., and Yoshihara H. Rinsho. Byori. 37 (1989) 1392
3. Shiota G., Fukada J., Ito T., Tsukizawa M., Yamada M., et al. Jpn. J. Med. 28 (1989) 22
4. Ito S., Tsuji Y., Kitagawa N., Akihiko I., Syundo J., et al. Hepatology 8 (1988) 383
5. Crary G.S., Yasmineh W.G., Snover D.C., and Vine W. Transplant. Proc. 21 (1989) 2315
6. Durak I., Beduk Y., Kavutcu M., Suzer O., Yaman O., et al. Cancer Invest. 15 (1997) 212
7. Yuan G., Bin J.C., McKay D.J., and Snyder F.F. J. Biol. Chem. 274 (1999) 8175
8. Paletzki R.F. Neuroscience 109 (2002) 15
9. Canbolat O., Durak I., Cetin R., Kavutcu M., Demirci S., et al. Breast Cancer. Res. Treat. 37 (1996) 189
10. Kaneshige Y., Matsumoto H., Chiba S., Hashimoto S., and Noro H. Rinsho. Shinkeigaku. 29 (1989) 854
11. Baker B.R. J. Med. Chem. 10 (1967) 59
12. Baker B.R., and Santi D.V. J. Med. Chem. 10 (1967) 62
13. Baker B.R., and Siebeneick H.U. J. Med. Chem. 14 (1971) 802
14. Baker B.R., and Siebeneick H.U. J. Med. Chem. 14 (1971) 799
15. Baker B.R., and Wood W.F. J. Med. Chem. 10 (1967) 1106
16. Baker B.R., and Wood W.F. J. Heterocycl. Chem. 10 (1967) 1101
17. Baker B.R., and Wood W.F. J. Med. Chem. 11 (1968) 650
18. Baker B.R., and Wood W.F. J. Med. Chem. 11 (1968) 644
19. Baker B.R., and Wood W.F. J. Med. Chem. 12 (1969) 216
20. Bhan A., and Hosmane R.S. Tetrahedron Lett. 35 (1994) 6831
21. Bhan A., and Hosmane R.S. Nucleosides Nucleotides 14 (1995) 455
22. Dietrich L.S., and Shapiro D.M. J. Biol. Chem. 203 (1953) 89
23. Kanzawa F., Hoshi A., and Kuretani K. Chem. Pharm. Bull. 19 (1971) 1737
24. Kanzawa F., Hoshi A., Nishimoto T., and Kuretani K. Chem. Pharm. Bull. 18 (1970) 392
25. Kumar S., Josan V., Sanger K.C.S., Tewari K.K., and Krishnan P.S. Biochem. J. 102 (1967) 691
26. Lucacchini A., Bazzichi L., Biagi G., Livi O., and Segnini D. Ital. J. Biochem. 31 (1982) 153
27. Lucacchini A., Montali U., and Segnini D. Ital. J. Biochem. 26 (1977) 27
28. Lucacchini A., Segnini D., Da Settimo A., and Livi O. Ital. J. Biochem. 28 (1979) 194
29. Meyer Jr. R.B., and Skibo E.B. J. Med. Chem. 22 (1979) 944
30. Rajappan V., and Hosmane R.S. Bioorg. Med. Chem. Lett. 8 (1998) 3649
31. Rajappan V.P., and Hosmane R.S. Nucleosides Nucleotides 17 (1998) 1141
32. Rajappan V.P., and Hosmane R.S. Nucleosides Nucleotides 18 (1999) 835
33. Saxena A.K., Ahmad S., Shanker K., Bhargava K.P., and Kishor K. Pharmazie 35 (1980) 16
34. Saxena A.K., Ahmad S., Shanker K., and Kishor K. Pharmacol. Res. Commun. 16 (1984) 243
35. Silipo C., and Hansch C. J. Med. Chem. 19 (1976) 62
36. Wang L., and Hosmane R.S. Bioorg. Med. Chem. Lett. 11 (2001) 2893
37. Isshiki K., Takahashi Y., Iinuma H., Naganawa H., Umezawa Y., et al. J. Antibiot. (Tokyo) 40 (1987) 1461
38. Lewis A.S., and Glantz M.D. J. Biol. Chem. 249 (1974) 3862
39. Liaw S.-H., Chang Y.-J., Lai C.-T., Chang H.-C., and Chang G.-G. J. Biol. Chem. 279 (2004) 35479
40. 3: C, 42.86; H, 4.11; N, 28.56. Found: C, 42.97; H, 4.16; N, 28.45.
41. Bhan A., and Hosmane R.S. J. Heterocycl. Chem. 30 (1993) 1453
42. Robers D.A., and Ward W.H.J. Enzyme Inhibitors. Medicinal Chemistry: Principles and Practice. 2nd ed. (2002), The Royal Society of Chemistry, Cambridge, UK 70-71
43. Agarwal R.P., Cha S., Crabtree G.W., and Parks Jr. R.E. Coformycin and deoxycoformycin: tight-binding inhibitors of adenosine deaminase. Chemistry and Biology of Nucleosides and Nucleotides (1978), Academic Press, New York 159-197
44. Hosmane R.S., and Hong M. Biochem. Biophys. Res. Commun. 236 (1997) 88
45. Wang Z., and Quiocho F.A. Biochemistry 37 (1998) 8314