Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Carbohydrate Research

Volumn 344, Issue 7, 2009, Pages 841-850

  Cheng, Keguang ^a,b   Liu, Jun ^b   Liu, Xiaofeng ^c   Li, Honglin ^c,d   Sun, Hongbin ^b   Xie, Juan ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^d EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Click chemistry; Diabetes; Glucoconjugate; Glycogen phosphorylase; Inhibitor; Oleanolic acid

Indexed keywords

CLICK CHEMISTRY; DIABETES; GLUCOCONJUGATE; GLYCOGEN PHOSPHORYLASE; INHIBITOR; OLEANOLIC ACID;

ACIDS; BINDING ENERGY; COMPLEXATION; ESTERS; NITROGEN COMPOUNDS; PHOSPHORYLATION; SUGARS;

ENZYME ACTIVITY;

3 O [1 (METHYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 3 O [2 O (METHYL ALPHA DEXTRO GLUCOPYRANOSIDURONYL)ETHOXYCARBONYL] 3BETA HYDROXY OLEAN 12 EN 28 OIC ACID; 3 O [[1 (METHYL 2,3,4 TRI O ACETYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 3BETA HYDROXYOLEAN 12 EN 28 OIC ACID; 3 O [[1 (METHYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 3BETA HYDROXYOLEAN 12 EN 28 OIC ACID; 6 (METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDURONYL)HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 (METHYL ALPHA DEXTRO GLUCOPYRANOSIDURONYL)HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [2 (METHYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSYL)ETHANOYL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [2 (METHYL ALPHA DEXTRO GLUCOPYRANOSYL) ETHANOYL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [4 (METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSID 6 YLOXY) METHYL 1H 1,2,3 TRIAZOL 1 YL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [4 (METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDURONYLMETHYL) 1H 1,2,3 TRIAZOL 1 YL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [4 (METHYL ALPHA DEXTRO GLUCOPYRANOSID 6 YLOXY)METHYL 1H 1,2,3 TRIAZOL 1 YL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 [4 (METHYL ALPHA DEXTRO GLUCOPYRANOSIDURONYLMETHYL) 1H 1,2,3 TRIAZOL 1 YL]HEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 AZIDOHEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; 6 BROMOHEXYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; [1 (METHYL 2,3,4 TRI O ACETYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; ANTIDIABETIC AGENT; BENZYL 3 O (2 CHLOROETHOXYCARBONYL) 3BETA HYDROXYOLEAN 12 EN 28 OATE; BENZYL 3 O [2 O (METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDURONYL ETHOXYCARBONYL] 3BETA HYDROXYOLEAN 12 EN 28 OATE; BENZYL 3 O [[(METHYL 2,3,4 TRI O ACETYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 3BETA HYDROXYOLEAN 12 EN 28 OATE; BENZYL 3 O [[1 (METHYL 6 DEOXY ALPHA DEXTRO GLUCOPYRANOSID 6 YL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 3BETA HYDROXYOLEAN 12 EN 28 OATE; BENZYL 3 O PROPARGYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; GLYCOGEN PHOSPHORYLASE; METHYL 2,3,4 TRI O BENZYL 6 O PROPARGYL ALPAH DEXTRO GLUCOPYRANOSIDE; METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDURONIC ACID; OLEANOLIC ACID; PROPARGYL (METHYL 2,3,4 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSID)URONATE; PROPARGYL 3BETA HYDROXYOLEAN 12 EN 28 OATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

COMPUTER SIMULATION; GLYCOCONJUGATES; GLYCOGEN PHOSPHORYLASE; MOLECULAR STRUCTURE; OLEANOLIC ACID; STRUCTURE-ACTIVITY RELATIONSHIP;

ORYCTOLAGUS CUNICULUS;

EID: 65249125749     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.02.012     Document Type: Article

References (35)

1. Agius L. Best Pract. Res. Clin. Endocrin. Metab. 21 (2007) 587-605
2. Oikonomakos N.G., and Somsák L. Curr. Opin. Invest. Drugs 9 (2008) 379-395
3. Somsák L., Czifrák K., Tóth M., Bokor E., Chrysina E.D., Alexacou K.-M., Hayes J.M., Tiraidis C., Lazoura E., Leonidas D.D., Zographos S.E., and Oikonomakos N.G. Curr. Med. Chem. 15 (2008) 2933-2983
4. Baker D.J., Greenhaff P.L., and Timmons J.A. Expert Opin. Ther. Pat. 16 (2006) 459-466
5. Oikonomakos N.G. Curr. Protein Pep. Sci. 3 (2002) 561-586
6. 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) 4125-4128
7. 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) 459-465
8. Treadway J.L., Mendys P., and Hoover D.J. Expert Opin. Invest. Drugs 10 (2001) 439-454 and references cited therein
9. Pinotsis N., Leonidas D.D., Chrysina E.D., Oikonomakos N.G., and Mavridis I.M. Protein Sci. 12 (2003) 1914-1924
10. 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) 873-888
11. 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) 7835-7845
12. Juhasz L., Docsa T., Brunyaszki A., Gergely P., and Antus S. Bioorg. Med. Chem. 15 (2007) 4048-4056
13. 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) 394-399
14. Martin J.L., Johnson L.N., and Withers S.G. Biochemistry 29 (1990) 10745-10757
15. Martin J.L., Veluraja K., Ross K., Johnson L.N., Fleet G.W.J., Ramsden N.G., Bruce I., Orchard M.G., Oikonomakos N.G., Papageorgiou A.C., Leonidas D.D., and Tsitoura H.S. Biochemistry 30 (1991) 10101-10116
16. Wen X.A., Sun H.B., Liu J., Cheng K.G., Zhang P., Zhang L.Y., Hao J., Zhang L.Y., Ni P.Z., Zographos S.E., Leonidas D.D., Alexacou K.M., Gimisis T., Hayes J.M., and Oikonomakos N.G. J. Med. Chem. 51 (2008) 3540-3554
17. Chen J., Liu J., Zhang L.Y., Wu G.Z., Hua W.Y., Wu X.M., and Sun H.B. Bioorg. Med. Chem. Lett. 16 (2006) 2915-2919
18. Hao J., Zhang P., Wen X.A., and Sun H.B. J. Org. Chem. 73 (2008) 7405-7408
19. Cheng K.G., Zhang P., Liu J., Xie J., and Sun H.B. J. Nat. Prod. 71 (2008) 1877-1880
20. Dzubak P., Hajduch M., Vydra D., Hustova A., Kvasnica M., Biedermann D., Markova L., Urban M., and Sarek J. Nat. Prod. Rep. 23 (2006) 394-411
21. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
22. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3069
23. Kolb H.C., and Sharpless K.B. Drug Dis. Today 8 (2003) 1128-1137
24. Xie J. Eur. J. Org. Chem. (2002) 3411-3418
25. Mereyala H.B., Gurrala S.R., and Mohan S.K. Tetrahedron 55 (1999) 11331-11342
26. Moore M., and Norris P. Tetrahedron Lett. 39 (1998) 7027-7030
27. David O., Maisonneuve S., and Xie J. Tetrahedron Lett. 48 (2007) 6527-6530
28. Dondoni A., Massi A., and Aldhoun M. J. Org. Chem. 72 (2007) 7677-7687
29. Martin W.H., Hoover D.J., Armento S.J., Stock I.A., McPherson R.K., Danley D.E., Stevenson R.W., Barrett E.J., and Treadway J.L. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 1776-1781
30. Krülle T.M., Watson K.A., Gregoriou M., Johnson L.N., Crook S., Watkin D.J., Griffiths R.C., Nash R.J., Tsitsanou K.E., Zographos S.E., Oikonomakos N.G., and Fleet G.W.J. Tetrahedron Lett. 36 (1995) 8281-8294
31. Pan D., Tseng Y., and Hopfinger A.J. J. Chem. Inf. Comput. Sci. 43 (2003) 1591-1607
32. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shaw D.E., Shelley M., Perry J.K., Sander L.C., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739-1749
33. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235-242
34. Maestro; Version 7.5; Schrödinger LLC: New York, 2006.
35. LigPrep; Version 2.0; Schrödinger LLC: New York, 2006.