Synthesis, characterization, oxidative degradation, antibacterial activity and acetylcholinesterase/butyrylcholinesterase inhibitory effects of some new phosphorus(V) hydrazides

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 5130-5139

  Gholivand, Khodayar ^a   Hosseini, Zahra ^a   Farshadian, Sedigheh ^a   Naderi Manesh, Hossein ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Acetylcholinesterase butyrylcholinesterase inhibitory; Antibacterial activity; Oxidative degradation; Phosphorus(V) hydrazide

Indexed keywords

2 CHLORO N,N' BIS(4 AMINOMORPHOLINE)PHOSPHORAMIDIC ACID PHENYL ESTER; 2,6 DIFLUORO N BENZOYL N',N'' BIS(4 AMINOMORPHOLINE)PHOSPHORIC TRIAMIDE; 4 CHLORO N BENZOYL N',N'' BIS(4 AMINOMORPHOLINE)PHOSPHORIC TRIAMIDE; 4 METHOXY N BENZOYL N',N'' BIS(4 AMINOMORPHOLINE)PHOSPHORIC TRIAMIDE; 5,5' DITHIOBIS(2 NITROBENZOIC ACID); ACETYLCHOLINESTERASE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; COPPER ION; HYDRAZIDE DERIVATIVE; N BENZOYL N,N' BIS(4 AMINOMORPHOLINE)PHOSPHORIC TRIAMIDE; N BENZOYL N,N' BIS(4 AMINOPIPERIDINE)PHOSPHORIC TRIAMIDE; N,N' BIS(4 AMINOMORPHOLINE)PHENYLPHOSPONIC DIAMIDE; N,N' BIS(4 AMINOMORPHOLINE)PHOSPHORAMIDIC ACID (4 METHYLPHENYL)ESTER; N,N' BIS(4 AMINOMORPHOLINE)PHOSPHORAMIDIC ACID PHENYL ESTER; N,N' BIS(4 AMINOPIPERIDINE)PHENYLPHOSPONIC DIAMIDE; N,N' BIS(4 AMINOPIPERIDINE)PHOSPHORAMIDIC ACID PHENYL ESTER; PHENYL N (4 AMINOPIPERIDINE)PHOSPHATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHOLINESTERASE INHIBITION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; IN VITRO STUDY; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; NONHUMAN; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ACETYLCHOLINESTERASE; ANTI-BACTERIAL AGENTS; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIDATION-REDUCTION; PHOSPHORUS; PHOSPHORUS COMPOUNDS; SPECTROPHOTOMETRY, INFRARED;

EID: 77957850439     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.08.025     Document Type: Article

References (52)

1. M.E.Y. Francisco, H.H. Seltzman, A.F. Gilliam, R.A. Mitchell, S.L. Rider, R.G. Pertwee, L.A. Stevenson, and B.F. Thomas J. Med. Chem. 45 2002 2708 2719
2. M.G. Vigorita, T. Previtera, C. Zappala, A. Trovato, M.T. Monforta, R. Barbara, and F. Pizzimenti Farmaco 45 2 1999 223 235
3. X. Lin, I. King, M.F. Belcourt, W. Terrence Doyle, US 7,405,317B2, 2008, pp. 1-9.
4. J. Nawrot-Modranka, E. Nawrot, and J. Graczyk Eur. J. Med. Chem. 41 2006 1301 1309
5. J. Hernandez-Lopez, H.L. Khor, A. Caminade, J. Majoral, S. Mittler, W. Knoll, and D.H. Kim Thin Solid Films 516 2008 1256 1264
6. V. Chandrasekhar, R. Azhakar, J.F. Bickley, and A. Steiner Cryst. Growth Des. 6 2006 910 914
7. M.L. Clarke, G.L. Holliday, A.M.Z. Slawin, and J.D. Woollins Inorg. Chem. Commun. 4 2001 115 118
8. M.J.P. Harger Tetrahedron Lett. 42 2001 6749 6752
9. T.E.-S. Ali Arkivoc ii 2008 71 79
10. P.J. Blower Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem. 100 2004 633 658
11. F.M. Raushel, and S.B. Hong Biochemistry 38 1999 1159 1165
12. S.D. Cohen, R.A. Williams, J.M. Killinger, and R.I. Freudenthal Toxicol. Appl. Pharmacol. 83 1985 452 459
13. M. Jokanovic, M. Maksimovic, V. Kilibarda, D. Jovanovic, and D. Savic Toxicol. Lett. 85 1996 35 39
14. C.M. Thompson, J.A. Frick, B.C. Natke, and L.K. Hansen Chem. Res. Toxicol. 2 1989 386 391
15. M.R. Farlow, and P.A. Cyrus Dement. Geriatr. Cogn. Disord 11 2000 202 211
16. N.J. Zhang, and J.E. Casida Bioorg. Med. Chem. 10 2002 1281 1290
17. K. Law, R.A. Acey, C.R. Smith, D.A. Benton, S. Soroushian, B. Eckenrod, R. Stedman, K.A. Kantardjieff, and K. Nakayama Biochem. Biophys. Res. Commun. 355 2007 371 378
18. K. Gholivand, M. Abdollahi, F. Mojahed, A. Madani Alizadehgan, and G. Dehghan J. Enzyme Inhib. Med. Chem. 4 2008 1 11
19. K. Gholivand, A. Madani Alizadehgan, F. Mojahed, G. Dehghan, A. Mohammadirad, and M. Abdollahi Z. Naturforsch. 63c 2008 241 250
20. K. Gholivand, Z. Shariatinia, K. Khajeh, and H. Naderi-Manesh J. Enzyme Inhib. Med. Chem. 21 2006 31 35
21. K. Gholivand, F. Ghaziani, R. Yaghoubi, Z. Hosseini, Z. Shariatinia, J. Enzyme Inhib. Med. Chem., in press, doi:10.3109/14756361003691860.
22. G.L. Ellman, K.D. Coutney, V.R. Andres, and M. Featherstone Biochem. Pharmacol. 7 1961 91 95
23. R.A. Copeland Enzymes, A Practical Introduction to Structure, Mechanism, and Data Analysis second ed. 2000 John Wiley-VCH New York
24. A.V. Kirsanov, and R. Makitra J. Gen. Chem. 26 1956 905 907
25. H. Tolkimth Ann. N.Y. Acad. Sci. 79 1959 189 (Dow Chem. Co., Middland, Mich.) Art. 7
26. J.C. Gould, and J.H. Bowie Edinb. Med. J. 59 1952 178 199
27. K. Gholivand, M. Pourayoubi, Z. Shariatinia, and H. Mostaanzadeh Polyhedron 24 2005 655 662
28. K. Gholivand, Z. Shariatinia, S.M. Mashhadi, F. Daeepour, N. Farshidnasab, H.R. Mahzouni, N. Taheri, S. Amiri, and S. Ansar Polyhedron 28 2009 307 321
29. M. Ramaswamy, and P. Ramaswamy New J. Chem. 27 2003 968 974
30. S.H. Li, H.G. Shi, C.H. Sun, X.T. Li, S.P. Pang, Y.Z. Yu, and X.Q. Zhao J. Chem. Crystallogr. 39 2009 13 16
31. T.M. Klaptke, P. Mayer, A. Schulz, and J.J. Weigand Propellants Explos. Pyrotech. 29 2004 325 332
32. R. Willett, H. Place, and M. Middleton J. Am. Chem. Soc. 110 1988 8639 8650
33. E.A. Trush, V.M. Amirkhanov, V.A. Ovchynnikov, V.A. Ovchynnikov, J.S. Wiatekkozlowska, K.A. Lanikina, and K.V. Domasevitch Polyhedron 22 2003 1221 1229
34. V.V. Skopenko, V.M. Amirkhanov, T.Y. Silva, I.S. Vasilchenko, E.L. Anpilov, and A.D. Garnovski Russ. Chem. Rev. 73 2004 737 752
35. O.V. Moroz, V.A. Trush, I.S. Konovalova, O.V. Shishkin, Y.S. Moroz, S. Demeshko, and V.M. Amirkhanov Polyhedron 28 2009 1331 1335
36. A. Pop, A. Rotar, C. Rat, and A. Silvestru Inorg. Chim. Acta 361 2008 255 261
37. A. Diaz, R. Cao, and A. Garcia Monatsh. Chem. 125 1994 823 825
38. D.M. Brown, and N.K. Hamer Proc. Chem. Soc. 1960 212
39. R.J. Cremlin, M.J. Frearson, and D.R. Milnes Phosphorus and Sulfur 6 1976 207
40. T.G. Back, and R.G. Kerr Can. J. Chem. 60 1982 2711 2718
41. I. Bhatnagar, and M.V. George J. Org. Chem. 33 1968 2407 2411
42. J.R. Hwu, N. Wang, and R.T. Yung J. Org. Chem. 54 1989 1070 1073
43. K. Sugiyama, T. Nakaya, and M. Imoto Die Makromol. Chem 176 2003 587 592
44. W. Thun, and W. Mcbride J. Org. Chem. 34 1969 2997 3002
45. A. Sloboda, and A. Vogel Cancer Res. 24 1964 461 469
46. T.W. Schultz, M.T.D. Cronin, J.D. Walker, and A.O. Aptula J. Mol. Struct. (Theochem) 622 2003 1 22
47. M. Karelson, V.S. Lobanov, and A.R. Katritzky Chem. Rev. 96 1996 1027 1044
48. C. Hansch, and W. Dunn J. Pharm. Sci. 61 1972 1 19
49. D. Kaplan, A. Ordentlich, D. Barak, N. Ariel, C. Kronman, B. Velan, and A. Shafferman Biochemistry 40 2001 7433 7445
50. S. Riazzo, C. Riviere, L. Piazzi, A. Bisi, S. Gobbi, M. Bartolini, V. Andrisano, F. Morroni, A. Tarozzi, J.P. Monti, and A. Rampa J. Med. Chem. 51 2008 2883 2886
51. Bruker, SMART. Bruker Molecular Analysis Research Tool, v. 5.059 1998 Bruker AXS Madison, Wisconsin, USA
52. G.M. Sheldrick Programs SHELXS97 (Crystal Structure Solution) and SHELXL97 (Crystal Structure Refinement) 1997 University of Gottingen Germany