Synthesis of novel phosphorothioates and phosphorodithioates and their differential inhibition of cholinesterases

Bioorganic Chemistry

Volumn 37, Issue 4, 2009, Pages 101-105

  Kaboudin, Babak ^a   Emadi, Saeed ^a   Hadizadeh, Atefeh ^a  

^a INSTITUTE FOR ADVANCED STUDIES IN BASIC SCIENCES IASBS   (Iran)

Author keywords

Anticholinesterase; Enzyme inhibitors; Phosphorodithioates; Phosphorothioates

Indexed keywords

[2 (1,3 DIOXO 1,3 DIHIDRO ISOINDOL 2 YL) ETHYL]O,O' DIETHYLPHOSPHOROTHIOATE; [6 (DIETHOXY THIOPHOSPHORYLSULFANYLMETHYL)PYRIDIN 2YLMETHYL]O,O'DIETHYLPHOSPHOROTHIOATE; ACETYLCHOLINESTERASE; ANTIINFECTIVE AGENT; CHOLINESTERASE; PHOSPHOROTHIOIC ACID DERIVATIVE; PYRIDIN 2 YLMETHYL O,O' DIETHYL PHOSPHOROTHIOATE; PYRIDIN 2 YLMETHYL O,O' DIETHYLPHOSPHORODITHIOATE; PYRIDIN 4 YLMETHYL O,O' DIETHYL PHOSPHOROTHIOATE; PYRIDIN 4 YLMETHYL O,O' DIETHYLPHOSPHORODITHIOATE; QUINOLIN 2 YLMETHYL O,O' DIETHYL PHOSPHOROTHIOATE; QUINOLIN 2 YLMETHYL O,O' DIETHYLPHOSPHORODITHIOATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHOBICITY; IC 50; PRIORITY JOURNAL;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; INSECTICIDES; ORGANOTHIOPHOSPHORUS COMPOUNDS; PHOSPHATES;

EID: 67650095584     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2009.05.002     Document Type: Article

References (38)

1. Hilderbrand R.L. The Role of Phosphonates in Living Systems (1982), CRC Press, Boca Raton, Fl
2. Kaboudin B. Phosphorus Sulfur Silicon Relat. Elem. 177 (2002) 1749
3. Fest C., and Schmidt K.-J. The Chemistry of Organophosphorus Pesticides (1982), Springer-Verlag, Berlin-Heidelberg-New York
4. Crooke S.T., and Bennett C.F. Annu. Rev. Pharmacol. Toxicol. 36 (1996) 107
5. Elzagheid M.I., Mattila K., Oivanen M., Jones B.C.N.M., Cosstick R., and Lonnberg H. Eur. J. Org. Chem. (2000) 1987
6. Kaboudin B., Emadi S., and Norouzi H. Phosphorus Sulfur Silicon Relat. Elem. 179 (2004) 585
7. Enz A., Amstutz R., Boddeke H., Gmelin G., and Malanowski J. Prog. Brain Res. 98 (1993) 431
8. Millard C.B., and Broomfield C.A. J. Neurochem. 64 (1995) 1909
9. Lindner A., Schalke B., and Toyka K.V. J. Neurol. 244 (1997) 515
10. Sussman J.L., Harel M., Frolow F., Oefner C., and Goldman A. Science 253 (1991) 872
11. Uhlman E., and Peyman A. Chem. Rev. 90 (1990) 543
12. Stein C.A., and Cheng Y.C. Science 261 (1993) 1004
13. M. Yoshido, T. Maeda, H. Sugiyama, Japanese Patent 1541 (C1.16 C 92), 1967
14. Yoshido M., Maeda T., and Sugiyama H. Chem. Abstr. 66 (1967) 115455
15. Kabachnik M.I., Abduvakhabov A.A., Agabekova I.I., and Brestkin A.P. Russ. Chem. Rev. 39 (1970) 485
16. Casida J.E., and Quistad G.B. Chem. Res. Toxicol. 17 (2004) 983
17. Buratti F.M., Leoni C., and Testai E. J. Consum. Protect. Food Safety 2 (2007) 37
18. Kaboudin B., and Farjadian F. Beilstein J. Org. Chem. 2 (2006) 4
19. Kaboudin B., and Norouzi H. Tetrahedron Lett. 45 (2004) 1283
20. Kaboudin B. Tetrahedron Lett. 43 (2002) 8713
21. Ellman G.L., Countney K.D., Andres V., and Featherstone R.M. Biochem. Phamacol. 7 (1961) 88
22. Maxwell D.M., and Brecht K.M. Chem. Res. Toxicol. 5 (1992) 66
23. Vellom D.C., Radić Z., Li Y., Pickering N.A., Camp S., and Taylor P. Biochemistry 32 (1993) 12
24. Masson P., Froment M.T., Bartels C.F., and Lockridge O. Eur. J. Biochem. 235 (1996) 36
25. Nicolet Y., Lockridge O., Masson P., Fontecilla-Camps J.C., and Nachon F. J. Biol. Chem. 278 (2003) 41141
26. Kaplan D., Ordentlich A., Barak D., Ariel N., Kronman C., Velan B., and Shafferman A. Biochemistry 40 (2001) 7433
27. Harel M., Sussman J.L., Krejci E., Bon S., Chanal P., Massoulie J., and Silman I. Proc. Natl. Acad. Sci. USA 89 (1992) 10827
28. Cyger M., Schrag J.D., Sussman J.L., Harel M., Silman I., Gentry M.K., and Doctor B.P. Protein Sci. 2 (1993) 366
29. Friboulet A., Rieger F., Goudou D., Amitai G., and Taylor P. Biochemistry 29 (1990) 914
30. Szegletes T., Mallender W.D., and Rosenberry T.L. Biochemistry 37 (1998) 4206
31. Szegletes T., Mallender W.D., Thomas P.J., and Rosenberry T.L. Biochemistry 38 (1999) 122
32. Mallender W.D., Szegletes T., and Rosenberry T.L. J. Biol. Chem. 274 (1999) 8491
33. Bourne Y., Taylor P., Radić Z., and Marchot P. EMBO J. 22 (2003) 1
34. Branduardi D., Gervasio F.L., Cavalli A., Recanatini M., and Parrinello M. J. Am. Chem. Soc. 127 (2005) 9147
35. Colletier J.P., Fournier D., Greenblatt H.M., Stojan J., Sussman J.L., Zaccai G., Silman I., and Weik M. EMBO J. 25 (2006) 2746
36. Quinn D.M. Chem. Rev. 87 (1987) 955
37. Taylor P. J. Biol. Chem. 266 (1991) 4025
38. Sussman J.L., Harel M., Frolow F., Oefner C., Goldman A., Toker L., and Silman I. Science 253 (1991) 872