Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 19, 2009, Pages 6937-6941

  Yan, Jian ^a,b   Sun, Lirong ^c   Wu, Guisheng ^a   Yi, Ping ^a   Yang, Fumei ^d   Zhou, Lin ^a   Zhang, Xianmin ^a   Li, Zhongrong ^a   Yang, Xiaosheng ^d   Luo, Huairong ^a   Qiu, Minghua ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b SOUTH CHINA INSTITUTE OF BOTANY   (China)

^c SOUTHERN MEDICAL UNIVERSITY   (China)

^d INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

AChE; Alzheimer's disease; Docking study; Hupzine A

Indexed keywords

AMINOPHENOL; ANTIDEPRESSANT AGENT; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; HELICID; HELICID NILGRINICA EXTRACT; HUPERZINE A; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; INSOMNIA; NEURALGIA; NEURASTHENIA; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; COMPUTER SIMULATION; DRUG DESIGN; HUMANS; NEUROPROTECTIVE AGENTS; PROTEIN BINDING; SCHIFF BASES; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 69949113207     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.08.017     Document Type: Article

References (45)

1. Hebert L.E., Scherr P.A., Bienias J.L., Bennett D.A., and Evans D.A. Arch. Neurol. 60 (2003) 1119
2. Lahiri D.K., Lewis S., and Farlow M.R. J. Neurosci. Res. 37 (1994) 777
3. Kawakami Y., Inoue A., Kawai T., Wakita M., Sugimoto H., and Hopfinger A.J. Bioorg. Med. Chem. 4 (1996) 1429
4. Enz A., Boddeke H., Gray J., and Spiegel R. Ann. N.Y. Acad. Sci. 640 (1991) 272
5. Marco-Contelles J., Carreiras M.D.C., Rodriguez C., Villarroya M., and Garcia A.G. Chem. Rev. 106 (2006) 116
6. Bai D.L., Tang X.C., and He X.C. Curr. Med. Chem. 7 (2000) 355
7. Wang R., Yan H., and Tang X.C. Acta Pharmacol. Sin. 27 (2006) 1
8. Qian L.G., and Ji R.Y. Tetrahedron Lett. 30 (1989) 208
9. Xia Y., and Kozikowski A.P. J. Am. Chem. Soc. 111 (1989) 4116
10. Kozikowski A.P., Xia Y., Reddy E.R., Tuckmantel W., Hanin I., and Tang X.C. J. Org. Chem. 56 (1991) 4636
11. Campiani G., Sun L.Q., Kozikowski A.P., Aagaard P., and McKinney M.A. J. Org. Chem. 58 (1993) 7660
12. Ma X.Q., and Gang D.R. Phytochemistry 69 (2008) 2022
13. Kozikowski A.P., Campiani G., Sun L.Q., Wang S.M., Saxena A., and Doctor B.P. J. Am. Chem. Soc. 118 (1996) 11357
14. Kozikowski A.P., Miller C.P., Yamada F., Pang Y.P., Miller J.H., McKinney M., and Ball R.G. J. Med. Chem. 34 (1991) 3399
15. Xia Y., Reddy E.R., and Kozikowski A.P. Tetrahedron Lett. 30 (1989) 3291
16. Campiani G., Kozikowski A.P., Wang S., Ming L., Nacci V., Saxena A., and Doctor B.P. Bioorg. Med. Chem. Lett. 8 (1998) 1413
17. Rajendran V., Prakash K.R., Ved H.S., Saxena A., Doctor B.P., and Kozikowski A.P. Bioorg. Med. Chem. Lett. 10 (2000) 2467
18. Rajendran V., Rong S.B., Saxena A., Doctor B.P., and Kozikowski A.P. Tetrahedron Lett. 42 (2001) 5359
19. Zhu, D.; Tang, X.; Lin, J.; Zhu, C.; Shen, J.; Wu, G.; Jiang, S.; Yamaguchi, T.; Tanaka, K. PCT Int Appl WO 9911625.
20. Li C., Du F., Yu C., Xu X., Zheng J., Xu F., and Zhu D. Rapid Commun. Mass Spectrom. 18 (2004) 651
21. Raves M.L., Harel M., Pang Y.P., Silman I., Kozikowski A.P., and Sussman J.L. Nat. Struct. Biol. 4 (1997) 57
22. Haviv H., Wong D.M., Greenblatt H.M., Carlier P.R., Pang Y.P., Silman I., and Sussman J.L. J. Am. Chem. Soc. 127 (2005) 11029
23. Dvir H., Wong D.M., Harel M., Barril X., Orozco M., Luque F.J., Munoz-Torrero D., Camps P., Rosenberry T.L., Silman I., and Sussman J.L. Biochemistry 41 (2002) 2970
24. Kryger G., Silman I., and Sussman J.L. Structure 7 (1999) 297
25. Greenblatt H.M., Guillou C., Guenard D., Badet B., Thal C., Silman I., and Sussman J.L. J. Am. Chem. Soc. 126 (2004) 15405
26. Pang Y.P., Quiram P., Jelacic T., Hong F., and Brimijoin S. J. Biol. Chem. 271 (1996) 23646
27. Jin G.Y., Luo X.M., He X.C., Jiang H.L., Zhang H.Y., and Bai D.L. Arzneim.-Forsch. 53 (2003) 753
28. Feng S., Wang Z.F., He X.C., Zheng S.X., Xia Y., Jiang H.L., Tang X.C., and Bai D.L. J. Med. Chem. 48 (2005) 655
29. Carlier P.R., Du D.M., Han Y., Liu J., and Pang Y.P. Bioorg. Med. Chem. Lett. 9 (1999) 2335
30. Roman S., Badia A., Camps P., and Clos M.V. Neuropharmacology 46 (2004) 95
31. Mary A., Renko D.Z., Guillou C., and Thal C. Bioorg. Med. Chem. 6 (1998) 1835
32. Guillou C., Mary A., Renko D.Z., Gras E., and Thal C. Bioorg. Med. Chem. Lett. 10 (2000) 637
33. Greenblatt H.M., Guillou C., Guenard D., Argaman A., Botti S., Badet B., Thal C., Silman I., and Sussman J.L. J. Am. Chem. Soc. 126 (2004) 15405
34. Harel M., Schalk I., Ehret-Sabatier L., Bouet F., Goeldner M., Hirth C., Axelsen P.H., Silman I., and Sussman J.L. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 9031
35. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker L., and Silman I. Science 253 (1991) 872
36. Axelsenx P.H., Harel M., Silman I., and Sussman J.L. Protein Sci. 3 (1994) 188
37. Wanibuchi K., Zhang P., Abe T., Morita H., Kohno T., Chen G., Noguchi H., and Abe I. FEBS J. 274 (2007) 1073
38. Ellman G.L., Courtney K.D., Andres V., and Featherstone R.M. Biochem. Pharmacol. 7 (1961) 88
39. Ma X.Q., and Gang D.R. Nat. Prod. Rep. 21 (2004) 752
40. Du D.M., and Carlier P.R. Curr. Pharm. Des. 10 (2004) 3141
41. Ros E., Aleu J., Gomez de Aranda I., Munoz-Torrero D., Camps P., Badia A., Marsal J., and Solsona C. Eur. J. Pharmacol. 421 (2001) 77
42. Carlier P.R., Du D.M., Han Y.F., Liu J., Perola E., Williams I.D., and Pang Y.P. Angew. Chem., Int. Ed. 39 (2000) 1775
43. Liu P., Gen J.M., Li J., Na D.K., and Shang L. Chin. Tradit. Patent Med. 24 (2002) 38
44. Wen H., Lin C., Que L., Ge H., Ma L., Cao R., Wan Y., Peng W., Wang Z., and Song H. Eur. J. Med. Chem. 43 (2008) 166
45. Wang, Z.; Hu, L. K.; Luo, Z. P.; Li, Y. F.; Zhao, N.; Wang, Z. H.; Wang, Y. H.; Chen., Y. G.. PCT Int. Appl., WO 2004054591.