Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 21, 2007, Pages 5777-5782

  Wen, Xiaoan ^a   Xia, Jun ^a   Cheng, Keguang ^a   Zhang, Liying ^a   Zhang, Pu ^a   Liu, Jun ^a   Zhang, Luyong ^a   Ni, Peizhou ^a   Sun, Hongbin ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Corosolic acid; Derivatives; Glycogen phosphorylase; Inhibitor; SAR; Synthesis

Indexed keywords

ANTIDIABETIC AGENT; CAFFEINE; COROSOLIC ACID DERIVATIVE; ENZYME INHIBITOR; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE INHIBITOR; MUSCLE ENZYME; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIABETES MELLITUS; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GLUCOSE METABOLISM; HYPOGLYCEMIA; METABOLIC REGULATION; MUSCLE; NONHUMAN; RABBIT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ENZYME INHIBITORS; GLYCOGEN PHOSPHORYLASE; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

ORYCTOLAGUS CUNICULUS;

EID: 34548833897     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.08.057     Document Type: Article

References (30)

1. Miura T., Itoh Y., Kaneko T., Ueda N., Ishida T., Fukushima M., Matsuyama F., and Seino Y. Biol. Pharm. Bull. 27 (2004) 1103
2. Liu F., Kim J., Li Y., Liu X., Li J., and Chen X. J. Nutr. 131 (2001) 2242
3. Judy W.V., Hari S.P., Stogsdill W.W., Judy J.S., Naguib Y.M.A., and Psswater R. J. Ethnopharmacol. 87 (2003) 115
4. Fukushima M., Matsuyama F., Ueda N., Egawa K., Takemoto J., Kajimoto Y., Yonaha N., Miura T., Kaneko T., Nishi Y., Mitsui R., Fujita Y., Yamada Y., and Seino Y. Diabetes Res. Clin. Pract. 73 (2006) 174
5. Na M.K., Yang S.M., He L., Oh H., Kim B.S., Oh W.K., Kim B.Y., and Ahn J.S. Planta Med. 72 (2006) 261
6. Murakami C., Myoga K., Kasai R., Ohtani K., Kurokawa T., Ishibashi S., Dayrit F., Padolina W.G., and Yamasaki K. Chem. Pharm. Bull. 41 (1993) 2129
7. Wen X.A., Sun H.B., Liu J., Wu G.Z., Zhang L.Y., Wu X.M., and Ni P.Z. Bioorg. Chem. Med. Lett. 15 (2005) 4944
8. Greenberg C.C., Jurczak M.J., Danos A.M., and Brady M.J. Am. J. Physiol. Endocrinol. Metab. 291 (2006) E1
9. Baker D.J., Greenhaff P.L., and Timmons J.A. Expert Opin. Ther. Patents 16 (2006) 459
10. Oikonomakos N.G. Curr. Protein Pept. Sci. 3 (2002) 561
11. Somsák L., Nagy V., Hadady Z., Docsa T., and Gergely P. Curr. Pharm. Des. 9 (2003) 1177
12. Lu Z.J., Bohn J., Bergeron R., Deng Q.L., Ellsworth K.P., Geissler W.M., Harris G., McCann P.E., Mckeever B., Myers R.W., Saperstein R., Willoughby C.A., Yao J., and Chapman K. Bioorg. Med. Chem. Lett. 13 (2003) 4125
13. Wright S.W., Rath V.L., Genereux P.E., Hageman D.L., Levy C.B., McClure L.D., McCoid S.C., McPherson R.K., Schelhorn T.M., Wilder D.E., Zavadoski W.J., Gibbs E.M., and Treadway J.L. Bioorg. Med. Chem. Lett. 15 (2005) 459
14. Treadway J.L., Mendys P., and Hoover D.J. Expert Opin. Invest. Drugs 10 (2001) 439 and references therein
15. Chrysina E.D., Kosmopolou M.N., Tiraidis C., Kardarakis R., Bischler N., Leonidas D.D., Hadady Z., Somsak L., Docsa T., Gergely P., and Oikonomakos N.G. Protein Sci. 14 (2005) 873
16. Hampson L.J., Arden C., Agius L., Ganotidis M., Kosmopoulou M.N., Tiraidis C., Elemes Y., Sakarellos C., Leonidas D.D., and Oikonomakos N.G. Bioorg. Med. Chem. 14 (2006) 7835
17. Juhasz L., Docsa T., Brunyaszki A., Gergely P., and Antus S. Bioorg. Med. Chem 15 (2007) 4048
18. Birch A.M., Kenny P.W., Oikonomakos N.G., Otterbein L., Schofield P., Whittamore P.R.O., and Whalley D.P. Bioorg. Med. Chem. Lett. 17 (2007) 394
19. Wen X.A., Zhang P., Liu J., Zhang L.Y., Wu X.M., Ni P.Z., and Sun H.B. Bioorg. Med. Chem. Lett. 16 (2006) 722
20. Takayama, H.; Kitajima, M.; Ishizuka, T.; Seo, S. U.S. Patent Application: US2005020681 A1, 2005.
21. Huneck S., and Snatzke G. Chem. Ber. 98 (1965) 120
22. Bore L., Honda T., and Gribble G.W. J. Org. Chem. 65 (2000) 6278
23. 4-H: 471.3474; Found: 471.3485.
24. 4-H-H: 557.3631; Found: 557.3651.
25. 4-H: 471.3474; Found: 471.3481.
26. Martin W.H., Hoover D.J., Armento S.J., Stock I.A., Mcpherson R.K., Danley D.E., Stevenson R.W., Barretti E.J., and Treadway J.L. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 1776
27. Bollen M., Keppens S., and Stalmans W. Biochem. J. 336 (1998) 19 Part 1
28. Aiston S., Coghlan M.P., and Agius L. Eur. J. Biochem. 270 (2003) 2773
29. Aiston S., Hampson L.J., Arden C., Iynedjian P.B., and Agius L. Diabetologia 49 (2006) 174
30. Aiston S., Hampson L., Gomez-Foix A.M., Guinovart J.J., and Agius L. J. Biol. Chem. 276 (2001) 23858