Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 13, 2014, Pages 3537-3543

  Güney, Murat ^a,b   Coşkun, Ahmet ^c   Topal, Fevzi ^b,d   Daştan, Arif ^b   Gülçin, Ilhami ^b,e   Supuran, Claudiu T ^f  

^a AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

^b ATATÜRK UNIVERSITY   (Turkey)

^c NECMETTIN ERBAKAN UNIVERSITY   (Turkey)

^d GUMUSHANE UNIVERSITY   (Turkey)

^e KING SAUD UNIVERSITY   (Saudi Arabia)

^f UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Benzocycloheptatriene; Benzotropone; Carbonic anhydrase inhibition; Nitrile substituted drugs; Oxidation; Rearrangement

Indexed keywords

5 OXO 5H BENZOCYCLOHEPTENE 6 CARBONITRILE; 5 OXO 5H BENZOCYCLOHEPTENE 7 CARBONITRILE; 5H BENZOCYCLOHEPTENE 7 CARBONITRILE; 7 OXO 7H BENZOCYCLOHEPTENE 6 CARBONITRILE; 9 OXO 9H BENZOCYCLOHEPTENE 6 CARBONITRILE; 9H BENZOCYCLOHEPTENE 6 CARBONITRILE; ACETAZOLAMIDE; BENZOTROPONE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CHROMIUM DERIVATIVE; CHROMIUM TRIOXIDE; CYANOBENZOCYCLOHEPTATRIENE DERIVATIVE; ENZYME INHIBITOR; ISOENZYME; UNCLASSIFIED DRUG; CARBONATE DEHYDRATASE INHIBITOR; TROPOLONE; TROPONE;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOOXIDATION; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; ISOENZYMES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; STRUCTURE-ACTIVITY RELATIONSHIP; TROPOLONE;

EID: 84901938556     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.04.007     Document Type: Article

References (91)

1. M.J.S. Dewar Nature 155 1945 50
2. M. Ohkita, K. Sano, T. Suzuki, and T. Tsuji Tetrahedron Lett. 42 2001 7295
3. S. Takahashi, T. Kamiya, K. Saeki, T. Nezu, S. Takeuchi, R. Takasawa, S. Sunaga, A. Yoshimori, S. Ebizuka, T. Abe, and S. Tanuma Bioorg. Med. Chem. 18 2010 8112
4. F. Pietra Acc. Chem. Res. 12 1979 132
5. F. Pietra Chem. Rev. 73 1973 293
6. A. Coşkun, M. Güney, A. Daştan, and M. Balci Tetrahedron 63 2007 4944
7. M.G. Banwell Aust. J. Chem. 44 1991 1
8. A. Najda-Bernatowicz, M. Krawczyk, A. Stankiewicz-Drogon, M. Bretner, and A.M. Boguszewska-Chachulska Bioorg. Med. Chem. 18 2010 5129
9. W. Li, H. Li, and Z. Li Tetrahedron Lett. 51 2010 5448
10. U. Albrecht, T.H.V. Nguyen, and P. Langer J. Org. Chem. 69 2004 3417
11. M. Gill, and W. Steglich Prog. Chem. Org. Nat. Prod. 51 1987 216
12. M. Levy, M. Spino, and S.E. Read Pharmacotherapy 11 1991 196
13. H.J.C. Yeh, M. Chrzanowska, and A. Brossi FEBS Lett. 229 1988 82
14. Q. Shi, K. Chen, A. Brossi, P. Verdier-Pinard, E. Hamel, A.T. McPhail, and K.H. Lee Helv. Chim. Acta 81 1998 1023
15. Q. Shi, P. Verdier-Pinard, A. Brossi, E. Hamel, A.T. McPhail, and K.H. Lee J. Med. Chem. 40 1997 961
16. O. Boye, and A. Brossi A. Brossi, The Alkaloids Vol. 41 1983 Academic Press New York 125
17. M.G. Banwell, M.A. Fam, R.W. Gable, and E. Hamel J. Chem. Soc., Chem. Commun. 21 1994 2647
18. N. Arpin, J. Fauvre-Bovin, and W. Steglich Phytochemistry 13 1974 1949
19. G. Baisch, B. Wagner, and R. Öhrlein Tetrahedron 66 2010 3742
20. W. Dürckheimer, and E.F. Paulus Angew. Chem. 97 1985 219 Angew. Chem., Int. Ed. Engl. 1985, 24, 224
21. F.F. Fleming, L.H. Yao, P.C. Ravikumar, L. Funk, and B.C. Shook J. Med. Chem. 53 2010 7902
22. P.F. Ranken, B.J. Harty, L. Kapicak, and M.A. Battiste Synth. Commun. 3 1973 311
23. S.D. Saraf Synthesis 5 1971 264
24. M. Sato, T. Tanaka, J. Tsunetsugu, and S. Ebine Bull. Chem. Soc. Jpn. 48 1975 2395
25. M. Ohkita, S. Nishida, and T. Tsuji J. Am. Chem. Soc. 121 1999 4589
26. G.D. Ewing, and L.A. Paquette J. Org. Chem. 40 1975 2965
27. L. Kerschensteiner, F. Löbermann, W. Steglich, and D. Trauner Tetrahedron 67 2011 1536
28. K.C. Srivastava, and S. Dev Tetrahedron 28 1972 1083
29. A. Dastan, Y.K. YIldIz, C. Kazaz, and M. Balci Turk. J. Chem. 26 2002 143
30. A. Dastan, N. Saracoglu, and M. Balci Eur. J. Org. Chem. 2001 3519
31. M. Oda, and Y. Kitahara Tetrahedron Lett. 38 1969 3295
32. T. Asao, M. Yagihara, and Y. Kitahara Bull. Chem. Soc. Jpn. 51 1978 2131
33. A. Daştan, and M. Balci Tetrahedron 62 2006 4003
34. M. Güney, A. Daştan, and M. Balci Helv. Chim. Acta 88 2005 830
35. D. Shahwar, M.A. Raza, and T. Khan Turk. J. Chem. 36 2012 257
36. O. Güzel-Akdemir, A. Akdemir, P. Pan, A.B. Vermelho, S. Seppo Parkkila, A. Scozzafava, C. Capasso, and C.T. Supuran J. Med. Chem. 56 2013 5773
37. I. Gülçin, Ş. Beydemir, and M.E. Büyü kokuroǧlu Biol. Pharm. Bull. 27 2004 613
38. Ş. Beydemir, and I. Gülçin J. Enzyme Inhib. Med. Chem. 19 2004 193
39. C.T. Supuran Future Med. Chem. 3 2011 1165
40. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
41. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone Chem. Rev. 112 2012 4421
42. K.K. Sethi, S.M. Verma, M. Tanç, F. Carta, and C.T. Supuran Bioorg. Med. Chem. 21 2013 5168
43. M. Aggarwal, and R. McKenna Expert Opin. Ther. Pat. 22 2012 903
44. A. AkIncIoǧlu, Y. Akbaba, H. Göçer, S. Göksu, I. Gülçin, and C.T. Supuran Bioorg. Med. Chem. 21 2013 379
45. A. AkIncIoǧlu, M. Nar, I. Gülçin, and S. Göksu Arch. Pharm. 347 2014 68
46. H. Göçer, A. AkIncIoǧlu, N. ÖztaşkIn, S. Göksu, and I. Gülçin Arch. Pharm. 346 2013 783
47. K. Aksu, M. Nar, M. Tanç, D. Vullo, I. Gülçin, S. Göksu, F. Tümer, and C.T. Supuran Bioorg. Med. Chem. 21 2013 2925
48. Y. Akbaba, A. AkIncIoǧlu, H. Göçer, S. Göksu, I. Gülçin, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 29 2014 35
49. C.T. Supuran Curr. Pharm. Des. 14 2008 641
50. F. Mincione, A. Scozzafava, and C.T. Supuran C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 139 154
51. A. Thiry, J.M. Dogne, B. Masereel, and C.T. Supuran Curr. Top. Med. Chem. 7 2007 855
52. G. De Simone, A. Di Fiore, and C.T. Supuran Curr. Pharm. Des. 14 2008 655
53. L. Dubois, N.G. Lieuwes, A. Maresca, A. Thiry, C.T. Supuran, A. Scozzafava, B.G. Wouters, and P. Lambin Radiother. Oncol. 92 2009 423
54. J.K. Ahlskog, C.E. Dumelin, S. Trüssel, J. Marlind, and D. Neri Bioorg. Med. Chem. Lett. 19 2009 4851
55. F. Buller, M. Steiner, K. Frey, D. Mircsof, J. Scheuermann, M. Kalisch, P. Bühlmann, C.T. Supuran, and D. Neri Chem. Biol. 6 2011 336
56. A. Menzek, A. Altundas, and D. Gultekin J. Chem. Res. Synop. 11 2003 752
57. R.M. Balenkenship, K.A. Burdett, and J.S. Swenton J. Org. Chem. 39 1974 2300
58. C. Mayor, and W.M. Jones Tetrahedron Lett. 44 1977 3855
59. J.S. Swenton, K.A. Burdett, D.M. Madigan, and P.D. Rosso J. Org. Chem. 40 1975 1280
60. A. Dastan, Y.K. YIldIz, and M. BalcI Synth. Commun. 31 2001 3807
61. M. Güney, Z.C. Çelik, A. Daştan, and M. Balci Can. J. Chem. 83 2005 227
62. M. Balci Chem. Rev. 81 1981 91
63. M. Çelik, N. Akbulut, and M. Balci Helv. Chim. Acta 83 2000 3131
64. M. Balci, and B. Atasoy Tetrahedron Lett. 25 1984 4033
65. B. Atasoy, and M. Balci Tetrahedron 42 1986 1461
66. M.E. Şengül, Z. Ceylan, and M. Balci Tetrahedron 53 1997 10401
67. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
68. W.S. Sly, and P.Y. Hu Annu. Rev. Biochem. 64 1995 375
69. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
70. C.T. Supuran Carbonic Anhydrases: Catalytic Mechanism, Distribution and Physiological Roles C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase-Its Inhibitors and Activators 2004 CRC Boca Raton FL, USA 1 24
71. R. Ulus, I. Yesildag, M. Tanç, M. Bülbül, M. Kaya, and C.T. Supuran Bioorg. Med. Chem. 21 2013 5799
72. S.B. Sarikaya, I. Gülçin, and C.T. Supuran Chem. Biol. Drug Des. 75 2010 515
73. T.A. Çoban, Ş. Beydemir, I. Gülçin, and D. Ekinci Biol. Pharm. Bull. 30 2007 2257
74. Ş. ArasHisar, O. Hisar, Ş. Beydemir, I. Gülçin, and T. YanIk Acta Vet. Hung. 52 2004 413
75. D.K. Laemmli Nature 227 1970 680
76. I. Gülçin, Ö.I. Küfrevioǧlu, and M. Oktay J. Enzyme Inhib. Med. Chem. 20 2005 297
77. O. Hisar, Ş. Beydemir, I. Gülçin, Ö.I. Küfrevioǧlu, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 20 2005 35
78. Ş. Beydemir, I. Gülçin, O. Hisar, Ö.I. Küfrevioǧlu, and T. YanIk J. Appl. Anim. Res. 28 2005 65
79. T.A. Çoban, Ş. Beydemir, I. Gülçin, and D. Ekinci J. Enzyme Inhib. Med. Chem. 23 2008 266
80. J.A. Verpoorte, S. Mehta, and J.T. Edsall J. Biol. Chem. 242 1967 4221
81. M. Şentürk, I. Gülçin, A. Daştan, Ö.I. Küfrevioǧlu, and C.T. Supuran Bioorg. Med. Chem. 17 2009 3207
82. T.A. Coban, S. Beydemir, I. Gücin, D. Ekinci, A. Innocenti, D. Vullo, and C.T. Supuran Bioorg. Med. Chem. 17 2009 5791
83. M.M. Bradford Anal. Biochem. 72 1976 248
84. E. Köksal, and I. Gülçin Protein Peptide Lett. 15 2008 320
85. M. Şentürk, I. Gülçin, M. Çiftci, and Ö.I. Küfrevioǧlu Biol. Pharm. Bull. 31 2008 2036
86. D.P. Iga, R. Schmidt, S. Iga, C.L. Hotoleanu, F. Duica, A. Nicolescu, and S.S. Gitman Turk. J. Chem. 37 2013 299
87. H. Lineweaver, and D. Burk Am. Chem. Soc. 56 1934 658
88. Y. Çetinkaya, H. Göçer, A. Menzek, and I. Gülçin Arch. Pharm. 345 2012 323
89. A. Innocenti, I. Gülçin, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 5050
90. S.B. Öztürk SarIkaya, F. Topal, M. Şentürk, I. Gülçin, and C.T. Supuran Bioorg. Med. Chem. Lett. 21 2011 4259
91. H.T. BalaydIn, M. Senturk, S. Goksu, and A. Menzek Eur. J. Med. Chem. 54 2012 423