Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: A chemical model for possible biologically relevant properties of molybdenum-containing enzymes

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 11, 2012, Pages 3676-3681

  Litvić, Mladen ^a   Regović, Maja ^a   Šmic, Karolina ^a   Lovrić, Marija ^a,b   Filipan Litvić, Mirela ^a  

^a BELUPO Pharmaceuticals   (Croatia)

^b Galapagos Research Center Ltd   (Croatia)

Author keywords

1,4 Dihydropyridines; Aromatization; Dealkylation; Molybdenum oxytetrachloride; Molybdenum pentachloride

Indexed keywords

1,4 DIHYDROPYRIDINE; ACETONITRILE; ALDEHYDE OXIDASE; DICHLOROMETHANE; ESTER DERIVATIVE; MOLYBDENUM; PYRIDINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; VANADIUM; XANTHINE OXIDASE;

AROMATIZATION; ARTICLE; CHEMICAL MODEL; CONTROLLED STUDY; DRUG METABOLISM; LIVER; RESPIRATORY CHAIN; ROOM TEMPERATURE;

ALDEHYDE OXIDASE; CHLORIDES; DIHYDROPYRIDINES; ESTERS; MODELS, CHEMICAL; MOLYBDENUM; XANTHINE OXIDASE;

EID: 84861197093     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.043     Document Type: Article

References (112)

1. G. Schwarz, R.R. Mendel, and M.W. Ribbe Nature 460 2009 839
2. C. Kisker, H. Schindelin, and D.C. Rees Annu. Rev. Biochem. 66 1997 233
3. R.R. Mendel Planta 203 1997 399
4. R. Hille Essays Biochem. 34 1999 125
5. R.R. Mendel J. Exp. Bot. 58 2007 2289
6. R.R. Mendel, and R. Hänsch J. Exp. Bot. 53 2002 1689
7. W.H. Campbell Plant Physiol. 111 1996 355
8. R. Hille Chem. Rev. 96 1996 2757
9. R.R. Mendel, A.G. Smith, A. Marquet, and M.J. Warren Nat. Prod. Rep. 24 2007 963
10. J.L. Johnson, B.E. Hainline, K.V. Rajagopalan, and B.H. Arison J. Biol. Chem. 259 1984 5414
11. H. Bortels Arch. Mikrobiol. 1 1930 333
12. E.C. De Renzo, E. Kaleita, P.G. Heytler, J.J. Oleson, B.L. Hutchins, and J.H. Williams Arch. Biochem. Biophys. 45 1953 247
13. E.I. Stiefel J. Chem. Soc., Dalton Trans. 1 1997 3915
14. J.L. Johnson, B.E. Hainline, and K.V. Rajagopalan J. Biol. Chem. 259 1984 5414
15. C.G. Young, and A.G. Wedd Chem. Commun. 1997 1251
16. S. Gutteridge, S.J. Tanner, and R.C. Bray Biochem. J. 175 1978 869
17. M.P. Coughlan J. Inherit. Metab. 6 1983 70
18. S. Kitamura, K. Sugihara, and S. Ohta Drug Metab. Pharmacokinet. 21 2006 83
19. B.A. Appignani, E.M. Kaye, and S.M. Wolpert AJNR 17 1996 317
20. A. Roth, C. Nogus, J.P. Monnet, H. Ogier, and J.M. Sandubray Virchows Arch. [A] 405 1985 379
21. G. Schwarz, J.A. Santamaria-Araujo, S. Wolf, H.-J. Lee, I.M. Adham, H.-J. Gröne, H. Schwegler, J.O. Sass, T. Otte, P. Hänzelmann, R.R. Mendel, W. Engel, and J. Reiss Hum. Mol. Gen. 13 2004 1249
22. R.W. Klecker, R.L. Cysyk, and J.M. Collins Bioorg. Med. Chem. 14 2006 62
23. C. Gu, R. Collins, D.D. Holsworth, G.S. Walker, and R.L. Voorman Drug Metab. Dispos. 34 2006 2044
24. R.A. Torres, K.R. Korzekwa, D.R. McMasters, C.M. Fandozzi, and J.P. Jones J. Med. Chem. 50 2007 4642
25. K. Kawashima, K. Hosoi, T. Naruke, T. Shiba, M. Kitamura, and T. Watabe Drug Metab. Dispos. 27 1999 422
26. A. Parkinson Biotransformation of Xenobiotics, in Casarett and Doull's Toxicology: The Basic Science of Poison 6th ed. 2001 McGraw-Hill New York p 133
27. Y. Ashikawa, Z. Fujimoto, H. Noguchi, H. Habe, T. Omori, H. Yamane, and H. Nojiri Structure 14 2006 1779
28. I.A. Schepetkin, N.V. Cherdyntseva, and V.T. Kagiya Patophysiology 8 2001 119
29. M. Terao, M. Kurosaki, M.M. Barzago, E. Varasano, A. Boldetti, A. Bastone, M. Fratelli, and E. Garattini J. Biol. Chem. 281 2006 19748
30. K. Itoh, A. Masubuchi, T. Sasaki, M. Adachi, N. Watanabe, K. Nagata, Y. Yamazoe, M. Hiratsuka, M. Mizugaki, and Y. Tanaka Drug Metab. Dispos. 35 2007 734
31. W.M. Atkins, and S.G. Sligar J. Biol. Chem. 263 1988 18842
32. J.-A. Stevenson, A.C.G. Westlake, C. Whittock, and L.-L. Wong J. Am. Chem. Soc. 118 1996 12846
33. A.E. Rettie, and M.B. Fisher T.F. Wolf, Handbook of Drug Metabolism 1999 Marcel Dekker New York 131
34. G. Grün, and A. Fleckenstein Arzneimittelforschung (Drug Res.) 22 1972 334
35. F. Bossert, H. Meyer, and E. Wehinger Angew. Chem. 93 1981 755
36. R.A. Janis, and D.J. Triggle J. Med. Chem. 26 1983 775
37. B. Berkels, R. Roesen, S. Dhein, U. Fricke, and W. Klaus Cardiovasc. Drug Rev. 17 1999 179
38. T. Tsuruo, H. Iida, M. Nojiri, S. Tsukagoshi, and Y. Sakurai Cancer Res. 43 1983 2905
39. R.W. Chapman, G. Danko, and M.I. Siegels Pharmacology 29 1984 282
40. W.J. Malaise, and P.C.F. Mathias Diabetologia 28 1985 153
41. A. Krauze, S. Germane, O. Eberlins, I. Sturms, V. Klusa, and G. Duburs Eur. J. Med. Chem. 34 1999 301
42. R. Peri, S. Padmanabhan, S. Singh, A. Rutledge, and D.J. Triggle J. Med. Chem. 43 2000 2906
43. X. Zhou, L. Zhang, E. Tseng, E. Scott-Ramsay, J.J. Schentag, R.A. Coburn, and M.E. Morris Drug Metab. Dispos. 33 2005 321
44. R.H. Böcker, and F.P. Guengerich J. Med. Chem. 28 1986 1596
45. S. Kudo, H. Okumura, G. Miyamoto, and T. Ishizaki Drug Metab. Dispos. 27 1999 303
46. H.R. Memarian, M. Abdoli-Senejani, and S. Tangestaninejad J. Iran Chem. Soc. 3 2006 285
47. J.J. Vanden Eynde, R. D'Ozario, and Y. Van Haverbeke Tetrahedron 50 1994 2479
48. B. Karami, M. Montazerozohori, M.H. Habibi, and M.A. Zolfigol Heterocycl. Commun. 11 2006 513
49. J.J. Vanden Eynde, F. Delfosse, A. Mayence, and Y. Van Haverbeke Tetrahedron 51 1995 6511
50. M.C. Bagley, and M.C. Lubinu Synthesis 2006 1283
51. M. Litvić, I. Cepanec, M. Filipan, K. Kos, A. Bartolinč ić, V. Drušković, M.M. Tibi, and V. Vinković Heterocycles 65 2005 23
52. M. Filipan-Litvić, M. Litvić, I. Cepanec, and V. Vinković ARKIVOC xi 2008 96
53. M. Filipan-Litvić, M. Litvić, and V. Vinković Tetrahedron 64 2008 10912
54. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, H.R. Memarian, and I. Mohammadpoor-Baltork Synth. Commun. 30 2000 2945
55. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, I. Mohammadpoor-Baltork, and H.R. Memarian Synth. Commun. 30 2000 3919
56. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, I. Mohammadpoor-Baltork, and H.R. Memarian Synth. Commun. 30 2000 551
57. R.S. Varma, and D. Kumar J. Chem. Soc., Perkin Trans. 1 1999 1755
58. S.P. Chavan, S.W. Dantale, U.R. Kalkote, V.S. Jyothirmai, and R.K. Kharul Synth. Commun. 28 1998 2789
59. L. Chai, Y. Zhao, Q. Sheng, and Z.-Q. Liu Tetrahedron Lett. 2006 9283
60. S.P. Panchgalle, S.M. Choudhary, S.P. Chavan, and U.R. Kalkote J. Chem. Res. (S) 2004 550
61. S.H. Mashraqui, and M.A. Karnik Tetrahedron Lett. 39 1998 4896
62. A. Kamal, M. Ahmad, N. Mohd, and A.M. Hamid Bull. Chem. Soc. Jpn. 37 1964 610
63. N. Nakamichi, Y. Kawashita, and M. Hayashi Org. Lett. 4 2002 3955
64. R.E. Misner Diss. Abstr. 29B 1969 2817
65. M. Filipan-Litvić, M. Litvić, and V. Vinković Tetrahedron 64 2008 5649
66. M. Filipan-Litvić, M. Litvić, and V. Vinković Bioorg. Med. Chem. 16 2008 9276
67. T. Itoh, K. Nagata, Y. Matsuya, M. Miyazaki, and A. Ohsawa J. Org. Chem. 62 1997 3582
68. X.Q. Zhu, B.J. Zhao, and J.P. Cheng J. Org. Chem. 65 2000 8158
69. M.A. Zolfigol, M.H. Zebarjadian, M.M. Sadegh, I. Mohammadpoor-Baltork, H.R. Memarian, and M. Shamsipur Synth. Commun. 31 2001 929
70. K.J. Ko, and J.Y. Kim Tetrahedron Lett. 40 1999 3207
71. M. Nasr-Esfahani, M. Moghadam, S. Tangestaninejad, and V. Mirkhani Bioorg. Med. Chem. Lett. 15 2005 3276
72. M. Moghadam, M. Nasr-Esfahani, S. Tangestaninejad, and V. Mirkhani Bioorg. Med. Chem. Lett. 16 2006 2026
73. B. Karami, M. Montazerozohori, and M. Nasr-Esfahani Heterocycles 65 2005 2181
74. M. Nasr-Esfahani, M. Moghdam, and G. Valipour J. Iran Chem. Soc. 5 2008 244
75. B. Khadilkar, H. Jaisinghani, and A. Khare Ind. J. Chem. 37B 1998 817
76. K.Y. Ko, and J.Y. Park Bull. Korean Chem. Soc. 16 1995 200
77. M.M. Sadeghi, I. Mohammadpoor-Baltork, H.R. Memarian, and S. Sobhani Synth. Commun. 30 2000 1661
78. M.A. Zolfigol, P. Salehi, A. Ghorbani-Choghamarani, M. Safaiee, and M. Shahamirian Synth. Commun. 37 2007 1817
79. S.-H. Jin, J.-Y. Jin, and Y.-I. Kim Macromol. Res. 11 2003 501
80. H. Firouzabadi, A. Jamalian, and B. Karimi Bull. Chem. Soc. Jpn. 75 2002 1761
81. N.M. Boshta, M. Bomkamp, G. Schnakenburg, and S.R. Waldvogel Chem. Eur. J. 16 2010 3459
82. S.R. Waldvogel, E. Aits, C. Holst, and R. Fröhlich Chem. Commun. 2002 1278
83. B. Kramer, A. Averhoff, and S.R. Waldvogel Angew. Chem. Int. Ed. 41 2002 2981
84. S.R. Waldvogel Synlett 2002 622
85. D. Mirk, O. Kataeva, R. Fröhlich, and S.R. Waldvogel Synthesis 2003 2410
86. B. Kramer, R. Fröhlich, K. Bergander, and S.R. Waldvogel Synthesis 2003 91
87. B. Kramer, and S.R. Waldvogel Angew. Chem., Int. Ed. 43 2004 2446
88. D. Mirk, B. Wibbeling, R. Fröhlich, and S.R. Waldvogel Synlett 2004 1970
89. M. Bomkamp, A. Artiukhov, O. Kataeva, and S.R. Waldvogel Synthesis 2007 1107
90. A. Spurg, G. Schnakenburg, and S.R. Waldvogel Chem. Eur. J. 15 2009 13313
91. F.A. Cotton, and G. Wilkinson Advanced Inorganic Chemistry 5th ed. 1988 John Wiley & Sons, Inc. New York
92. T. Saito J. Chem. Soc., Dalton Trans. 1 1999 97
93. A.P. Krapcho ARKIVOC ii 2007 1
94. T.A. Krenitsky, S.M. Neil, G.M. Elion, and G.H. Hitchings Arch. Biochem. Biophys. 150 1972 585
95. L. Maia, R.O. Duarte, A. Ponces-Freire, J.J.G. Moura, and L. Mira J. Biol. Inorg. Chem. 12 2007 777
96. K. Yoshisue, H. Masuda, E. Matsushima, K. Ikeda, S. Nagayama, and Y. Kawaguchi Drug Metab. Dispos. 28 2000 1162
97. H.W. Davies, S.G. Britt, and L.R. Pohl Chem. Biol. Interact. 58 1986 345
98. P.R. Ortiz de Montellano, H.S. Beilan, and K.L. Kunze J. Biol. Chem. 256 1981 6708
99. F.P. Guengerich, and R.H. Böcker J. Biol. Chem. 263 1988 8168
100. C.H. Kennedy, and R.P. Mason J. Biol. Chem. 265 1990 11425
101. H. Aliyan, R. Fazaeli, A.R. Momeni, A.R. Massah, H.J. Naghash, and F. Khosravi Heterocycles 71 2007 2027
102. J.F. Alfaro, and J.P. Jones J. Org. Chem. 73 2008 9469
103. N. Benson, J.A. Farrar, A.G. McEwan, and A.J. Tomson FEBS 307 1992 169
104. K. Okamoto, K. Matsumoto, B.T. Eger, E.F. Pai, and T. Nishino PNAS 101 2004 7931
105. N.P. L'vov, A.N. Nosikov, and A.N. Antipov Biochemistry (Moscow) 67 2002 196
106. B. Loev, M.M. Goodman, K.M. Snader, R. Tedeschi, and E. Macko J. Med. Chem. 17 1974 956
107. H. Meyer, F. Bossert, and H. Horstmann Liebigs Ann. Chem. 1977 1888
108. A.P. Phillips J. Am. Chem. Soc. 72 1950 2780
109. M. Litvić, I. Cepanec, and V. Vinković Heterocycl. Commun. 9 2003 385
110. M. Litvić, M. Filipan, I. Pogorelić, and I. Cepanec Green Chem. 7 2005 771
111. H.R. Memarian, I. Mohammadpoor-Baltork, and M. Javahery J. Chin. Chem. Soc. 53 2006 511
112. B. Zeynizadeh, K.A. Dilmaghani, and A. Roozijoy J. Chin. Chem. Soc. 52 2005 1001