Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 3, 2007, Pages 1394-1408

  He, Xu Chang ^a   Feng, Song ^a   Wang, Zhi Fei ^a   Shi, Yufang ^a   Zheng, Suxin ^a   Xia, Yu ^a   Jiang, Hualiang ^a   Tang, Xi can ^a   Bai, Donglu ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Acetylcholinesterase; Alzheimer's disease; Dual site binding inhibitors; Huperzine B

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; DONEPEZIL; HUPERZINE A; HUPERZINE B; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLETHYL)HOMOPIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLETHYL)PIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL)CYCLOPROPYLAMINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL)HOMOPIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL)PIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL)PROPYLAMINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOETHYL)CYCLOPROPYLAMINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOETHYL)HOMOPIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOETHYL)PIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOETHYL)PROPYLAMINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOPROPYL)HOMOPIPERAZINE; N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOPROPYL)PIPERAZINE; N,N' DIMETHYL N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL) 1,12 DODECANEDIAMINE; N,N' DIMETHYL N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL) 1,3 PROPANEDIAMINE; N,N' DIMETHYL N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL) 1,8 OCTANEDIAMINE; N,N' DIMETHYL N,N' BIS(1 OXO 8,15 DIDEHYDROLYCODINOCARBONYLMETHYL) ETHYLENEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINO)ETHYL] 1,3 PROPANEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINO)ETHYL] 1,6 HEXANEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINO)ETHYL] 1,8 OCTANEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINO)ETHYL] ETHYLENEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINOCARBONYL)ETHYL) 1,6 HEXANEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINOCARBONYL)ETHYL] 1,10 DECADIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINOCARBONYL)ETHYL] 1,12 DODECANEDIAMINE; N,N' DIMETHYL N,N' BIS[2 (1 OXO 8,15 DIDEHYDROLYCODINOCARBONYL)ETHYL] 1,8 OCTANEDIAMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; COGNITION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; MOUSE; NEUROPROTECTION; NONHUMAN; RAT;

ACETYLCHOLINESTERASE; ALKALOIDS; ANIMALS; BINDING SITES; BUTYRYLCHOLINESTERASE; CEREBRAL CORTEX; CHOLINESTERASE INHIBITORS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33845986393     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.11.009     Document Type: Article

References (33)

1. Giacobini E. In: Giacobini E. (Ed). Cholinesterases and Cholinesterase Inhibitors (2000), Martin Dunitz, London 181-226
2. Barril X., Orozco M., and Luque F.J. Mini-Rev. Med. Chem. 1 (2001) 255
3. Palmer A.M. TIPS 23 (2002) 426
4. Ibach B., and Haen E. Curr. Pharm. Des. 10 (2004) 231
5. Francotte P., Graindorge E., Boverie S., de Tullio P., and Pirotte B. Curr. Med. Chem. 11 (2004) 1757
6. Robichaud A.J. Curr. Top. Med. Chem. 6 (2006) 553
7. Martinez A., and Castro A. Expert Opin. Investig. Drugs 15 (2006) 1
8. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker L., and Silman I. Science 253 (1991) 872
9. 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
10. Inestrosa N.C., Alvarez A., Perez C.A., Moreno R.D., Vicente M., Linker C., Casanueva O.I., Soto C., and Garrido J. Neuron 16 (1996) 881
11. Bartolini M., Bertucci C., Cavrini V., and Andrisano V. Biochem. Pharmacol. 65 (2003) 407
12. Castro A., and Martinez A. Mini-Rev. Med. Chem 1 (2001) 267
13. Dorronsoro I., Castro A., and Martinez A. Expert Opin. Ther. Patents 13 (2003) 1725
14. Pang Y.P., Quiram P., Jelacic T., Hong F., and Brimijoin S. J. Biol. Chem. 271 (1996) 23646
15. Carlier P.R., Han Y.F., Chow E.S.H., Li C.P.L., Wang H., Lieu T.X., Wong H.S., and Pang Y.P. Bioorg. Med. Chem. 7 (1999) 351
16. Jin G.Y., Luo X.M., He X.C., Jiang H.L., Zhang H.Y., and Bai D.L. Arzneim.-Forsch. 53 (2003) 753
17. 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
18. Wong D.M., Greenblatt H.M., Dvir H., Carlier P.R., Han Y.F., Pang Y.P., Silman I., and Sussman J.L. J. Am. Chem. Soc. 125 (2003) 363
19. Catherine G., Mary A., Renko D.Z., Gras E., and Thal C. Bioorg. Med. Chem. Lett. 10 (2000) 637
20. Zhu X.D., and Tang X.C. Acta Pharmacol. Sin. 9 (1988) 492
21. Xu H., and Tang X.C. Acta Pharmacol. Sin. 8 (1987) 18
22. Bai D.L., Tang X.C., and He X.C. Curr. Med. Chem. 7 (2000) 355
23. Yan X.F., Lu W.H., Lou J.W., and Tang X.C. Acta Pharmacol. Sin. 8 (1987) 117
24. Liu J., Zhang H.Y., Wang L.M., and Tang X.C. Acta Pharmacol. Sin. 20 (1999) 141
25. 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
26. Feng S., Xia Y., Han D., Zheng C., He X.C., Tang X.C., and Bai D.L. Bioorg. Med. Chem. Lett. 15 (2005) 523
27. Dvir H., Jiang H.L., Wong D.M., Harel M., Chetrit M., He X.C., Jin G.Y., Yu G.L., Tang X.C., Silman I., Bai D.L., and Sussman J.L. Biochemistry 41 (2002) 10810
28. Melchiorre C., Andrisano V., Bolognesi M.L., Budriesi R., Cavalli A., Cavrini V., Rosini M., Tuniatti V., and Recanatini M. J. Med. Chem 41 (1998) 4186
29. Cheng D.H., and Tang X.C. Pharmacol. Biochem. Behav. 60 (1998) 377
30. DOCK 4.0. Molecular Design Institute, San Francisco, CA, USA.
31. Ewing T.J.A., and Kuntz I.D. J. Comput. Chem. 18 (1997) 1175
32. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., and Hart W.E. J. Comput. Chem. 19 (1998) 1639
33. Wallace A.C., Laskowski R.A., and Thornton J.M. Protein Eng. 8 (1995) 127