Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 18, 2009, Pages 6761-6772

  Gökhan Kelekçi, Nesrin ^a   Şimşek, Ö Özgün ^a   Ercan, Ayşe ^a   Yelekçi, Kemal ^b   Şahin, Z Sibel ^c   Işik, Şamil ^c   Uçar, Gülberk ^a   Bilgin, A Altan ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

^b KADIR HAS UNIVERSITY   (Turkey)

^c ONDOKUZ MAYIS UNIVERSITY   (Turkey)

Author keywords

Docking; Hexahydroindazole; MAO A MAO B inhibition; X ray crystallographic model

Indexed keywords

3 (2 FURYL) 2 (N ALLYLTHIOCARBAMOYL) 3,3A,4,5,6,7 HEXAHYDRO 2H INDAZOLE; 3 (2 FURYL) 2 (N PHENYLTHIOCARBAMOYL) 3,3A,4,5,6,7 HEXAHYDRO 2H INDAZOLE; 3 (2 FURYL) 2 THIOCARBAMOYL 1,3,4,5,6,7 HEXAHYDRO 1H INDAZOLE DERIVATIVE; 3 (2 THIENYL) 2 (N PHENYLTHIOCARBAMOYL) 3,3A,4,5,6,7 HEXAHYDRO 2H INDAZOLE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; HEXAHYDROINDAZOLE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVE SITE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR DOCKING; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; CATALYTIC DOMAIN; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; INDAZOLES; MITOCHONDRIA, LIVER; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PROTEIN BINDING; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 69249111386     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.07.033     Document Type: Article

References (54)

1. Mondovi, B. Structure and Function of Amine Oxidases, CRC Press, Boca Raton, FL, 1985.
2. Westlund K.N., Denney R.M., Kochersperger L.M., and Rose R.M. Science 230 (1985) 181
3. Westlund K.N., Denney R.M., Rose R.M., and Abell C.W. Neuroscience 25 (1988) 439
4. Bousquet P., Feldman J., and Schwartz J. J. Pharmacol. Exp. Ther. 230 (1984) 232
5. Grimsby J., Lan N.C., Neve R., Chen K., and Shih J.C. J. Neurochem. 55 (1990) 1166
6. Rudorfer M.V., and Potter W.Z. Drugs 37 (1989) 713
7. Pacher P., Kohegyi E., Keckemetti V., and Furst S. Curr. Med. Chem. 8 (2001) 89
8. Pacher P., Keckemetti V., and Furst S. Curr. Med. Chem. 11 (2004) 925
9. Wouters J. Curr. Med. Chem. 5 (1998) 137
10. Tetrud J.W., and Langston J.W. Neurology 39 (1989) 1483
11. Carreiras M.C., and Marco J.L. Curr. Pharm. Des. 10 (2004) 3167
12. Binda C., Newton-Vinson P., Hubálek F., Edmondson D.E., and Mattevi A. Nat. Struct. Biol. 9 (2002) 22
13. Edmondson D.E., Binda C., and Mattevi A. Neurotoxicology 25 (2004) 63
14. De Colibus L., Li M., Binda C., Lustig A., Edmondson D.E., and Mattevi A.P. Natl. Acad. Sci. U.S.A. 102 (2005) 12684
15. Binda C., Hubálek F., Li M., Edmondson D.E., and Mattevi A. FEBS Lett. 564 (2004) 225
16. Binda C., Edmondson D.E., and Mattevi A. J. Biol.Chem. 277 (2002) 23973
17. Hubálek F., Binda C., Khalil A., Li M., Mattevi A., Castagnoli N., and Edmondson D.E. J. Biol. Chem. 280 (2005) 15761
18. Tipton K.F. Biochem. J. 128 (1972) 913
19. Mc Kenna K.F., Baker G.B., and Coutta R.T.N.S. Arch. Pharmacol. 343 (1991) 478
20. Yamada N., Takahashi S., Todd K.G., Baker G.B., and Paetsch P.R. J. Pharm. Sci. 82 (1993) 934
21. Belleau B., and Moran J. J. Med. Pharm. Chem. 5 (1962) 215
22. Parmar S.S., Pandey B.R., Dwivedi C., and Harbison R.D. J. Pharm. Sci. 63 (1974) 1152
23. Manna F., Chimenti F., Bolasco A., Bizzarri B., Befani O., Pietrangeli P., Mondovi B., and Turini P. J. Enzyme Inhib. 13 (1998) 207
24. Manna F., Chimenti F., Bolasco A., Secci D., Bizzarri B., Befani O., Turini P., Mondovi B., Alcaro S., and Tafi A. Bioorg. Med. Chem. Lett. 12 (2002) 3629
25. Gökhan N., Yeşilada A., Uçar G., Erol K., and Bilgin A.A. Arch. Pharm. 336 (2003) 362
26. Chimenti F., Maccioni E., Secci D., Bolasco A., Chimenti P., Granese A., Befani O., Turini P., Alcaro S., Ortuso F., Cirilli R., La Torre F., Cardia M.C., and Distinto S. J. Med. Chem. 48 (2005) 7113
27. Gökhan Kelekçi N., Yabanoǧlu S., Küpeli E., Salgi{dotless}n Gökşen U., Özgen O., Uçar G., Yeşilada E., Kendi E., Yeşilada A., and Bilgin A.A. Bioorg. Med. Chem. 15 (2007) 5775
28. Yeşilada A., Gökhan N., Özer I., Vural K., and Erol K. Farmaco 51 (1996) 775
29. Uçar G., Gökhan N., Yeşilada A., Yabanoǧlu S., and Bilgin A.A. Hacettepe Univ., J. Faculty Pharm. 25 (2005) 23
30. Yabanoǧlu S., Uçar G., Gökhan N., Salgi{dotless}n U., Yeşilada A., and Bilgin A.A. J. Neural. Transm. 114 (2007) 769
31. Gökhan-Kelekçi N., Koyunoǧlu S., Yabanoǧlu S., Yelekçi K., Özgen O., Uçar G., Erol K., Kendi E., and Yeşilada A. Bioorg. Med. Chem. 17 (2009) 675
32. Hassner A., and Michelson M.J. J. Org. Chem. 27 (1962) 298
33. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354
34. Youdim M.B.H., Edmondson D., and Tipton K.F. Nat. Rev. Neurosci. 7 (2006) 295
35. Fierro A., Osorio-Olivares M., Cassels B.K., Edmondson D.E., Sepulveda-Boza S., and Reyes-Parada M. Biiorg. Med. Chem. 15 (2007) 5198
36. Walton H.M. J. Org. Chem. 22 (1957) 1161
37. Sheldrick, G. M. shelxs97 and shelxl97, Program for Crystal Structure Solution, University of Göttingen: Germany, 1997.
38. Farrugia L. J. Appl. Crystallogr. 30 (1997) 565
39. Spek A.L. PLATON-A Multipurpose Crystallographic Tool (2005), Utrecht, Utrecht University, The Netherlands
40. Holt A., Sharman D.F., Baker G.B., and Pelcic M.M. Anal. Biochem. 244 (1997) 384
41. Bradford M.M. Anal. Biochem. 72 (1976) 248
42. Binda C., Hubalek F., Li M., Herzig Y., Sterling J., Edmondson D.E., and Mattevi A. J. Med. Chem. 47 (2004) 1767
43. Son S.Y., Ma J., Kondou Y., Yoshimura M., Yamashita E., and Tsukihara T. Proc. Natl. Acad. Sci. 105 (2008) 5739
44. Phillips J.C., Braun R., Wang W., Gumbart J., Tajkhorshid E., Villa E., Chipot C., Skeel R.D., Kale L., and Schulten K. J. Comput. Chem. 26 (2005) 1781
45. Feller S.E., Zhang Y.H., Pastor R.W., and Brooks B.R. J. Chem. Phys. 103 (1995) 4613
46. Humphrey W., Dalke A., and DalkeSchulten K. J. Mol. Graph. 14 (1996) 33
47. MacKerell Jr. A.D., Bashford D., Bellott M., Dunbrack Jr. R.L., Evanseck J., Field M.J., Fischer S., Gao J., Guo H., Ha S., et al. FASEB J. 6 (1992) A143
48. MacKerell Jr. A.D., Bashford D., Bellott M., Dunbrack Jr. R.L., Evanseck J., Field M.J., Fischer S., Gao J., Guo H., Ha S., et al. J. Phys. Chem. 102 (1998) 3586
49. Jorgensen W.L., Chandrasekhar J., Madura J.D., Impey R.W., and Klein M.L. J. Chem. Phys. 79 (1983) 926
50. Michel F., and Saner P. J. Mol. Graph. Model. 17 (1999) 57
51. Gasteiger J., and Marsili M. Tetrahedron 36 (1980) 3219
52. Wavefunction, Inc. 18401 von Karman Avenue, Suite 370, Spartan'02, Irvine, CA 92612, USA.
53. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A. J. Comput. Chem. 19 (1998) 1639
54. Huey R., Morris G.M., Olson A.J., and Goodsell D.S. J. Comput. Chem. 28 (2007) 1145