Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Benzothiophenones and Naphthothiophenone as Anticholinesterases
Corresponding Author(s) : D.I. Jung
Asian Journal of Chemistry,
Vol. 25 No. 10 (2013): Vol 25 Issue 10
Abstract
Since AChE and BuChE belong to the same serine hydrolazes, we designed and synthesized compounds 1-6 as anticholinesterases and measured their inhibition poteucies on ChEs. 7-Methoxy-3H-benzo[c]thiophen-1-one 4, 4,6-dibromo-5,7-methoxy-3H-benzo[c]thiophe-1-one 5 and 9-methoxy-3H-naphtho-[2,3-c]thiophen-1-one 6 were synthesized by using ethyl 2-methoxy-6-methylbenzoate, ethyl 3,4-dibromo-2,4-dimethoxy-6-methylbenzoate and ethyl 1-methoxy-3-methyl-2-naphthoate.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- T.L. Rosenberry, Adv. Enzymol. Rel. Areas Mol. Biol., 43, 103 (1975).
- T. Selwood, S.R. Feaster, M.J. States, A.N. Pryor and D.M. Quinn, J. Am. Chem. Soc., 113, 10477 (1993).
- P. Davies and A.J.F. Maloney, Lancet, 2, 1403 (1976)
- L. Parnetti, U. Senin and P. Mecocci, Drugs Future, 53, 752 (1997).
- E. Giacobini, J. Pharmacol. (Japan), 74, 225 (1997).
- B.L. Finkelstein, E.A. Benner, M.C. Hendrixson, K.T. Kranis, J.J. Rauh, M.R. Sethuraman and S.F. McCann, Bioorg. Med. Chem., 10, 599 (2002).
- P. Rocca, E. Cocuzza, L. Marchiaro and F. Bogetto, Prog. Neuropsychopharmacol. Biol. Psych., 26, 369 (2002).
- S.G. Potkin, R. Anand, K. Fleming, G. Alva, D. Keator, D. Carreon, D. Messina, J.C. Wu, R. Hartman and J.H. Fallon, Int. J. Neuropsychopharmacol., 4, 223 (2001).
- J. Barsan, M. Mewies, F.S. Mathews and N.S. Scrutton, Biochemistry, 36, 1989 (1997).
- K.N. Allen and R.H. Abeles, Biochemistry, 28, 8466 (1989).
- N.H. Greig, T. Utsuki, Q.S. Yu, X. Zhu, H.W. Holloway, T.A. Perry, B.H. Lee, D.K. Ingram and D.K. Lahai, Curr. Med. Res. Opin., 17, 1 (2001).
- N.H. Greig, T. Utsuki, Q.S. Yu, X. Zhu, H.W. Holloway, T.A. Perry, B.H. Lee, D.K. Ingram and D.K. Lahai, Alzheimer's Insight, 7, 1 (2001).
- H.K. Nair, K. Lee and D.M. Quinn, J. Am. Chem. Soc., 115, 9939 (1993).
- H.K. Nair, J. Seravalli, T. Arbuckle and D.M. Quinn, Biochemistry, 33, 8566 (1994).
- K.A. Koehler and G.P. Hess, Biochemisty, 13, 5345 (1974).
- F. Herz, E. Kaplan and I.G. Luna, Experientia, 27, 1260 (1971).
- K. Hemmi, J.W. Harper and J.C. Powers, Biochemistry, 24, 1841 (1985).
- N.H. Greig, T. Utsuki, Q.Yu, X. Zhu, H.W. Holloway, T. Perry, B. Lee, D.K. Ingram and D.K. Lahiri, Curr. Med. Res. Opin., 17, 159 (2001).
- R. Bullock, Int. J. Clin. Pract., 56, 206 (2002).
References
T.L. Rosenberry, Adv. Enzymol. Rel. Areas Mol. Biol., 43, 103 (1975).
T. Selwood, S.R. Feaster, M.J. States, A.N. Pryor and D.M. Quinn, J. Am. Chem. Soc., 113, 10477 (1993).
P. Davies and A.J.F. Maloney, Lancet, 2, 1403 (1976)
L. Parnetti, U. Senin and P. Mecocci, Drugs Future, 53, 752 (1997).
E. Giacobini, J. Pharmacol. (Japan), 74, 225 (1997).
B.L. Finkelstein, E.A. Benner, M.C. Hendrixson, K.T. Kranis, J.J. Rauh, M.R. Sethuraman and S.F. McCann, Bioorg. Med. Chem., 10, 599 (2002).
P. Rocca, E. Cocuzza, L. Marchiaro and F. Bogetto, Prog. Neuropsychopharmacol. Biol. Psych., 26, 369 (2002).
S.G. Potkin, R. Anand, K. Fleming, G. Alva, D. Keator, D. Carreon, D. Messina, J.C. Wu, R. Hartman and J.H. Fallon, Int. J. Neuropsychopharmacol., 4, 223 (2001).
J. Barsan, M. Mewies, F.S. Mathews and N.S. Scrutton, Biochemistry, 36, 1989 (1997).
K.N. Allen and R.H. Abeles, Biochemistry, 28, 8466 (1989).
N.H. Greig, T. Utsuki, Q.S. Yu, X. Zhu, H.W. Holloway, T.A. Perry, B.H. Lee, D.K. Ingram and D.K. Lahai, Curr. Med. Res. Opin., 17, 1 (2001).
N.H. Greig, T. Utsuki, Q.S. Yu, X. Zhu, H.W. Holloway, T.A. Perry, B.H. Lee, D.K. Ingram and D.K. Lahai, Alzheimer's Insight, 7, 1 (2001).
H.K. Nair, K. Lee and D.M. Quinn, J. Am. Chem. Soc., 115, 9939 (1993).
H.K. Nair, J. Seravalli, T. Arbuckle and D.M. Quinn, Biochemistry, 33, 8566 (1994).
K.A. Koehler and G.P. Hess, Biochemisty, 13, 5345 (1974).
F. Herz, E. Kaplan and I.G. Luna, Experientia, 27, 1260 (1971).
K. Hemmi, J.W. Harper and J.C. Powers, Biochemistry, 24, 1841 (1985).
N.H. Greig, T. Utsuki, Q.Yu, X. Zhu, H.W. Holloway, T. Perry, B. Lee, D.K. Ingram and D.K. Lahiri, Curr. Med. Res. Opin., 17, 159 (2001).
R. Bullock, Int. J. Clin. Pract., 56, 206 (2002).