Long-acting anticholinesterases for myasthenia gravis: Synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 13, 2010, Pages 4687-4693

  Yu, Qian Sheng ^a   Holloway, Harold W ^a   Luo, Weiming ^b   Lahiri, Debomoy K ^c   Brossi, Arnold ^d   Greig, Nigel H ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

^b MEDSTAR RESEARCH INSTITUTE   (United States)

^c INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

( ) Cymserine; ( ) Phenserine; Congenital myasthenic syndromes; Myasthenia gravis; N Phenylcarbamate analogues of ( ) physostigmine; Neostigmine; Pyridostigmine

Indexed keywords

ACETYLCHOLINESTERASE; CARBAMIC ACID DERIVATIVE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; LEVO PHENETHYLCYMSERINE; LEVO PHYSOSTIGMINE; LONG ACTING DRUG; METHYLAMMONIUM; N (1) METHYLAMMONIUM BROMIDE OF LEVO CYMSERINE; N (1) METHYLAMMONIUM BROMIDE OF LEVO PHENETHYLCYMSERINE; N (1) METHYLAMMONIUM BROMIDE OF LEVO PHENSERINE; N (1) METHYLAMMONIUM BROMIDE OF LEVO PHYSOSTIGMINE; N (1) METHYLAMMONIUM BROMIDE OF LEVO TOLSERINE; N PHENYLCARBAMATE OF 3 DIMETHYLAMINOPHENOL; N PHENYLCARBAMATE OF 3 HYDROXY 1 METHYLPYRIDINIUM BROMIDE; N PHENYLCARBAMATE OF 3 HYDROXYPYRIDINE; N PHENYLCARBAMATE OF 3 PHENOL 1 TRIMETHYLAMMONIUM METHYLSULFATE; NEOSTIGMINE METHYL SULFATE; PHENSERINE; PHYSOSTIGMINE; PYRIDOSTIGMINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MYASTHENIA GRAVIS; NONHUMAN; RAT;

ACETYLCHOLINESTERASE; ANIMALS; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; HUMANS; MICE; MYASTHENIA GRAVIS; NEOSTIGMINE; PHENYLCARBAMATES; PHYSOSTIGMINE; PYRIDOSTIGMINE BROMIDE;

RODENTIA;

EID: 77954218797     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.022     Document Type: Article

References (42)

1. Aeschliman, J.A. US Patent 1905990, 1933.
2. Urban, R. US Patent 2572579, 1951.
3. Howland, R. D.; Mycek, M. J.; Harvey, R. A.; Champe, P. C.; Mycek, M. J. In Pharmacology, 3rd ed.; Lippincott's Illustrated Reviews, 2008, p 51.
4. R. Gold, and C. Schneider-Gold Neurotherapeutics 5 2008 535
5. Z. Argov Curr. Opin. Neurol. 22 2009 493
6. M. Polonovski Bull. Soc. Chim. Fr. 19 1916 47 summarized in Beilstein E 1954, II, 23:333
7. N.H. Greig, X.-F. Pei, T.T. Soncrant, D.K. Ingram, and A. Brossi Med. Res. Rev. 15 1995 3
8. N.H. Greig, K. Sambamurti, Q.S. Yu, A. Brossi, G.B. Bruinsma, and D.K. Lahiri Curr. Alzheimer Res. 2 2005 281
9. J. Klein Expert Opin. Invest. Drugs 16 2007 1087
10. F. Varin, J. Couture, and H. Gao J. Chromatogr., B 723 1999 319
11. M. Broggini, C. Benvenuti, V. Botta, A. Fossati, and M. Valenti Methods Find Exp. Clin. Pharmacol. 13 1991 193
12. S.M. Aquilonius, and P. Hartvig Clin. Pharmacokinet. 11 1986 236
13. M. Brzostowska, X.-S. He, N.H. Greig, and A. Brossi Med. Chem. Res. 2 1992 238
14. X. Pei, Q.S. Yu, H.W. Holloway, A. Brossi, and N.H. Greig Med. Chem. Res. 9 1999 50
15. G.L. Ellman, K.D. Courtney, V. Andres Jr., and R.M. Feather-stone Biochem. Pharmacol. 7 1961 88
16. Q. Yu, H.W. Holloway, J.L. Flippen-Anderson, B. Hoffman, A. Brossi, and N.H. Greig J. Med. Chem. 44 2001 4062
17. A. McGrogan, S. Sneddon, and C.S. de Vries Neuroepidemiology 34 2010 171
18. B.M. Conti-Fine, M. Mikani, and H.J. Kaminski J. Clin. Invest. 116 2006 2843
19. T. Palmer S.L. Goodman, The Pharmacological Basis of Therapeutics 9th ed. 1996 Mcgraw-Hill Tx 173
20. S. Darvesh, D. Hopkins, and C. Geula Nat. Rev. Neurosci. 4 2003 131
21. H. Soreq, and H. Zakut Human Cholinesterases and Anticholinesterases 1993 Academic Press New York, NY
22. H. Soreq, and S. Seidman Nat. Rev. Neurosci. 2 2001 294
23. Q. Yu, H.W. Holloway, T. Utsuki, A. Brossi, and N.H. Greig J. Med. Chem. 42 1999 1855
24. Greig, N. H.; Yu, Q. S.; Brossi, A.; Matin, E.; Lahiri, D. K.; Darvesh, S. In Medicinal Chemistry of Alzheimeŕs Disease, Martinez, A., Ed.; Transworld Research Network, Research Signpost, Kerala, India, 2008, pp 79-109.
25. L. Savini, A. Gaeta, C. Fattorusso, B. Catalanotti, G. Campiani, L. Chiasserini, C. Pellerano, E. Novellino, D. McKissic, and A. Saxena J. Med. Chem. 46 2003 1
26. S. Darvesh, K.V. Darvesh, R.S. McDonald, D. Mataija, R. Walsh, S. Mothana, O. Lockridge, and E. Martin J. Med. Chem. 51 2008 4200
27. J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Science 253 1991 872
28. M. Harel, J.L. Sussman, E. Krejci, S. Bon, P. Chanal, J. Massoulie, and I. Silman Proc. Natl. Acad. Sci. U.S.A. 89 1992 10827
29. N. Zacharias, and D.A. Dougherty Trends Pharmacol. Sci. 23 2002 281
30. D. Gao, and C.G. Zhan J. Phys. Chem. B 109 2005 23070
31. A. Saxena, A.M. Redman, X. Jiang, O. Lockridge, and B.P. Doctor Biochemistry 36 1997 14642
32. Q.S. Yu, N.H. Greig, H.W. Holloway, F. Flippen-Anderson, and A. Brossi Med. Chem. Res. 10 2000 186
33. S. Asthana, N.H. Greig, L. Hegedus, H.H. Holloway, K.C. Raffaele, M.B. Schapiro, and T.T. Soncrant Clin. Pharmacol. Ther. 58 1995 299
34. M. Marta, F. Gatta, and M. Pomponi Biochim. Biophys. Acta 1120 1992 262
35. M. Brufani, C. Castellano, and M. Marta Pharmacol., Biochem. Behav. 26 1987 625
36. M.A. Kamal, N.H. Greig, A.S. Alhomida, and A.A. Al-Jafari Biochem. Pharmacol. 60 2000 561
37. M.A. Kamal, P. Klein, Q.S. Yu, D. Tweedie, Y. Li, H.W. Holloway, and N.H. Greig J. Alzheimers Dis. 10 2006 43
38. T. Mant, W.M. Troetel, and B.P. Imbimbo J. Clin. Pharmacol. 38 1998 610
39. N.H. Greig, J. Ruckle, P. Comer, L. Brownell, H.W. Holloway, D.R. Flanagan Jr., C.J. Canfield, and R.G. Burford Curr. Alzheimer Res. 2 2005 483
40. R.H. Paul, R.A. Cohen, J.M. Gilchrist, M.S. Aloia, and J.M. Goldstein J. Neurol Sci. 179 2000 59
41. E.J. Sitek, M.M. Biliska, D. Wieczorek, and W.M. Nyka Neurol. Sci. 30 2009 9
42. W. Luo, Q.S. Yu, M. Zhan, D. Parrish, J.R. Deschamps, S.S. Kulkarrni, H.W. Holloway, G.M. Alley, D.K. Lahiri, A. Brossi, and N.H. Greig J. Med. Chem. 48 2005 986