Design, synthesis and evaluation of difunctionalized 4-hydroxybenzaldehyde derivatives as novel cholinesterase inhibitors

Chemical and Pharmaceutical Bulletin

Volumn 58, Issue 9, 2010, Pages 1216-1220

  Yu, Liang ^a   Cao, Rihui ^a   Yi, Wei ^a   Yan, Qin ^a   Chen, Zhiyong ^a   Ma, Lin ^a   Song, Huacan ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

4 hydroxybenzaldehyde derivative; Cholinesterase inhibitor; Inhibition mechanism; Synthesis

Indexed keywords

1 [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]PIPERIDINE; 1 [8 [4 (PYRROLIDIN 1 YLMETHYL)PHENOXY]OCTYL]PIPERIDINE; 1 ETHYL 4 [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]PIPERAZINE; 1 METHYL 1 [8 [4 [(1 METHYLPYRROLIDINIUM 1 YL)METHYL]PHENOXY]OCTYL]PIPERIDINIUM IODIDE; 1 METHYL 4 [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]PIPERAZINE; 4 (8 BROMOOCTYLOXY)BENZALDEHYDE; CHOLINESTERASE INHIBITOR; N [4 (8 BROMOOCTYLOXY)BENZYL]N ETHYLETHANAMINE; N ETHYL N [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]BUTAN 1 AMINE; N ETHYL N [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]ETHANAMINE; N ETHYL N [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]MORPHOLINE; N ETHYL N [4 [8 (PIPERIDIN 1 YL)OCTYLOXY]BENZYL]N PROPYLPROPAN 1 AMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50;

ACETYLCHOLINESTERASE; ANIMALS; BENZALDEHYDES; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; ELECTROPHORUS; HORSES; MOLECULAR STRUCTURE;

EID: 77956325778     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.58.1216     Document Type: Article

References (26)

1. Silman I., Sussman J. L., Curr. Opin. Pharmacol., 5, 293-302 (2005).
2. Nachon F., Nicolet Y., Masson P., Ann. Pharm. Fr., 63, 194-206 (2005).
3. Shen Q., Peng Q., Shao J., Liu X. Huang Z., Pu X., Ma L., Li Y. M., Chan A. S., Gu L. Q., Eur. J. Med. Chem., 20, 1307-1315 (2005).
4. Ridrugyez-Franco M. I., Fernandez-Bachiller M. I., Perez C., Castro A., Martinez A., Bioorg. Med. Chem., 13, 6795-6802 (2005).
5. Greig N. H., Utsuki T., Yu Q., Zhu X., Holloway H. W., Perry T., Lee B., Ingram D. K., Lahiri D. K., Curr. Med. Res. Opin., 17, 159-165 (2001).
6. Giacobini E., Spiegel R., Enz A., Veroff A. E., Cutler N. R., J. Neural Trans., 109, 1053-1065 (2002).
7. Savini L., Gaeta A., Fattorusso C., Catalanotti B., Campiani G., Chiasserini L., Pellerano C., Novellino E., Mckissic D., Saxena A., J. Med. Chem., 46, 1-4 (2003).
8. Bolognesi M. L., Andrisano V., Bartolini M., Banzi R., Carlo Melchiorre C., J. Med. Chem., 48, 24-27 (2005).
9. Allen N. H. P., Burns A., J. Psychopharmacol., 9, 43-56 (1995).
10. Francis P. T., Palmer A. M., Snap M., Wilcock G. K., J. Neurol. Neurosurg. Psychiatry, 66, 137-147 (1999).
11. Ibach B., Haen E., Curr. Pharm. Des., 10, 231-251 (2004).
12. Galisteo M., Rissel M., Sergent O., Chevanne M., Cillard J., Guilouzo A., Lagadic-Gossmann D., J. Pharmacol. Exp. Ther., 294, 160-167 (2000).
13. Tang W., Eisenbrand G., "Chinese Drugs of Plant Origin. Chemistry, Pharmacology, and Use in Traditional and Modern Medicine," Springer Verlag, Berlin, 1992, pp. 545-547.
14. Hayashi J., Sekine T., Deguchi S., Lin Q., Horie S., Tsuchiya S., Yano S., Watanabe K., Ikegami F., Phytochemistry, 59, 513-519 (2002).
15. Wen H., Lin C. L., Que L., Peng W. L., Wang Z. H., Song H. C., Eur. J. Med. Chem., 43, 166-173 (2008).
16. Wen H., Zhou Y. Y., Lin C. L., Song H. C., Bioorg. Med. Chem. Lett., 17, 2123-2125 (2007).
17. Jia P., Sheng R., Zhang J., Fang L., He Q. J., Yang B., Hu Y. Z., Eur. J. Med. Chem., 44, 772-784 (2009).
18. Zhou X., Wang X. B., Wang T., Kong L. Y., Bioorg. Med. Chem., 16, 8011-8021 (2008).
19. Tang H., Wei Y. B., Zhang C., Ning F. X., Qiao W., Huang S. L., Ma L., Huang Z. S., Gu L. Q., Eur. J. Med. Chem., 44, 2523-2532 (2009).
20. Tang H., Ning F. X., Wei Y. B., Huang S. L., Huang Z. S., Chan A. S. C., Gu L.Q., Bioorg. Med. Chem. Lett., 17, 3765-3768 (2007).
21. Markmee S., Ruchirawat S., Prachyawarakorn V., Ingkaninan K., Khorana N., Bioorg. Med. Chem. Lett., 16, 2170-2172 (2006).
22. Ellman G. L., Courtney D. K., Andres V., Featherstone R. M., Biochem. Pharmacol., 7, 88-92 (1961).
23. Massoulie J., Bon S., Silman I., Prog. Brain Res., 98, 139-146 (1993).
24. Piazzi L., Belluti F., Bisi A., Gobbi S., Rampa A., Bioorg. Med. Chem., 15, 575-585 (2007).
25. Abdel-Magid A., Carson K., Harris B., J. Org. Chem., 61, 3849-3862 (1996).
26. Pang Y. P., Quiram P., Jelacic T., Hong F., Brimijoin S., J. Biol. Chem., 271, 23646-23649 (1996).