N-(1,3-Diaryl-3-oxopropyl)amides as a new template for xanthine oxidase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5569-5576

  Nepali, Kunal ^a   Agarwal, Amit ^b   Sapra, Sameer ^a   Mittal, Vineet ^a   Kumar, Raj ^a   Banerjee, Uttam C ^b   Gupta, Manish K ^a   Satti, Naresh K ^c   Suri, Om P ^a   Dhar, Kanaya L ^a  

^a Laboratory for Drug Design and Synthesis   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^c CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

Author keywords

Molecular docking; N (1,3 Diaryl 3 oxopropyl)amides; Non purine xanthine oxidase inhibitors; Xanthine oxidase

Indexed keywords

ALLOPURINOL; AMIDE; N ( 1 ANTHRACEN 9 YL 3 OXO 3 PHENYLPROPYL)ACETAMIDE; N (1 NAPHTHALEN 2 YL 3 OXO 3 PHENYLPROPYL)ACETAMIDE; N (1,3 DIARYL 3 OXOPROPYL)AMIDE; N (3 OXO 1,3 DIARYLPROPYL)ACETAMIDE; N (3 OXO 1,3 DIPHENYLPROPYL)ACETAMIDE; N (3 OXO 1,3 DIPHENYLPROPYL)BENZAMIDE; N [1 (2 NITROPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (2 OXO 2 PHENYLETHYL) 3 PHENYLALLYL]ACETAMIDE; N [1 (2,3,4 TRIMETHOXYPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (2,5 DIMETHOXYPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (3 BROMOPHENYL) 3 NAPHTHALEN 1 YL 3 OXOPROPYL]ACETAMIDE; N [1 (3 BROMOPHENYL) 3 NAPHTHALEN 2 YL 3 OXOPROPYL]ACETAMIDE; N [1 (3 BROMOPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (3 NITROPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (3,4,5 TRIMETHOXYPHENYL) 3 OXO 3 PHENYLPROPYL]ACETAMIDE; N [1 (4 METHOXYPHENYL) 3 (4 NITROPHENYL) 3 OXOPROPYL]ACETAMIDE; N [1 [2 (3 ACETYLAMINOPHENYL) 2 OXOETHYL] 3 PHENYLALLYL]ACETAMIDE; N [3 (3 ACETYLAMINOPHENYL) 1 (2,5 DIMETHOXYPHENYL) 3 OXOPROPYL]ACETAMIDE; N [3 (3 ACETYLAMINOPHENYL) 1 (3 NITROPHENYL) 3 OXOPROPYL]ACETAMIDE; N [3 (3 ACETYLAMINOPHENYL) 1 (4 CHLOROPHENYL) 3 OXOPROPYL]ACETAMIDE; N [3 (4 CHLOROPHENYL) 3 OXO 1 PHENYLPROPYL]ACETAMIDE; N [3 (4 NITROPHENYL) 3 OXO 1 PHENYLPROPYL]ACETAMIDE; N [3 FURAN 2 YL 1 (3 NITROPHENYL) 3 OXOPROPYL]ACETAMIDE; N [3 NAPHTHALEN 1 YL 1 (3 NITROPHENYL) 3 OXOPROPYL]ACETAMIDE; OTERACIL POTASSIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERURICEMIC ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; DRUG POTENTIATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYPERURICEMIA; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOLECULAR DOCKING; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MALE; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINE OXIDASE;

MUS;

EID: 80052583320     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.07.039     Document Type: Article

References (67)

1. A.L. Stockert, S.S. Shinde, R.F. Anderson, and R. Hille J. Am. Chem. Soc. 124 2002 14554
2. F. Borges, E. Fernandes, and F. Roleira Curr. Med. Chem. 9 2002 195
3. R. Hille Eur. J. Inorg. Chem. 2006 1913
4. P. Pacher, A. Nivorozhkin, and C. Szab Pharmacol. Rev. 58 2006 87
5. G.B. Elion, S. Callahan, H. Nathan, S. Bieber, R.W. Rundles, and G.H. Hitching Biochem. Pharmacol. 12 1963 85
6. H. Tamta, R. Thilagavathi, A.K. Chakraborti, and A.K. Mukhopadhyay J. Enzyme Inhib. Med. Chem. 20 2005 317
7. R. Kumar, S. Darpan Sharma, and R. Singh Expert Opin. Ther. Pat. 2011 10.1517/13543776.2011.577417
8. G. Biagi, I. Giorgi, F. Pacchini, O. Livi, and V. Scartoni IL Pharmaco. 51 2001 809
9. D.E. Brien, R.H. Springer, T.N.A. Albert, K. Senga, J.P. Miller, and D.G. Streeter J. Heterocycl. Chem. 22 1985 601
10. K. Oettl, and G. Reibneggar Biochim. Biophys. Acta 1430 1999 387
11. J.J. Baldwin, P.A. Kasinger, F.C. Novello, J.M. Sprague, and D.E. Duggan J. Med. Chem. 18 1975 895 900
12. J.J. Baldwin, P.K. Lumma, F.C. Novello, G.S. Ponticello, J.M. Sprague, and D.E. Duggan J. Med. Chem. 20 1977 1189
13. Y. Osada, M. Tsuchimoto, H. Fukushima, K. Takahashi, S. Kondo, M. Hasegawa, and K. Komoriya Eur. J. Pharmacol. 241 1993 183
14. K. Okamoto, B.T. Eger, T. Nishino, S. Kondo, E.F. Pai, and T. Nishino J. Biol. Chem. 278 2003 1848
15. P. Cos, L. Ying, M. Calomme, J.P. Hu, K. Cimanga, B.V. Poel, L. Pieters, A.J. Vlietincka, and D.V. Berghe J. Nat. Prod. 61 1998 71
16. D.E. Van Hoorn, R.J. Xijveidt, P.A. Van Leeuwen, Z. Hofman, L. Rabet, D.B. De Bont, and K. Van Norren Eur. J. Pharmacol. 451 2002 111
17. K. Okamoto, K. Matsumoto, R. Hille, B.T. Eger, E.F. Pai, and T. Nishino Proc. Natl. Acad. Sci. U.S.A. 101 2004 7931
18. L. Shen, and H.F. Ji Bioorg. Med. Chem. Lett. 19 2009 5990
19. K. Nepali, G. Singh, A. Turan, A. Agarwal, S. Sapra, R. Kumar, U.C. Banerjee, N.K. Satti, M.K. Gupta, O.P. Suri, and K.L. Dhar Bioorg. Med. Chem. 19 2011 1950 1958
20. J.R. Casimir, C. Turetta, L. Ettouati, and J. Paris Tetrahedron Lett. 36 1995 4797
21. A.G. Godfrey, D.A. Brooks, L.A. Hay, M. Peters, J.R. McCarthy, and D. Mitchell J. Org. Chem. 68 2003 2623
22. U. Dahn, H. Hagenmaier, H. Hohne, W.A. Konig, G. Wolf, and H. Zahner Arch. Microbiol. 107 1976 143
23. A.K. Tiwari, R.M. Kumbhare, S.B. Agawane, A.Z. Ali, and K.V. Kumar Bioorg. Med. Chem. Lett. 18 2008 4130
24. P. Dallemagne, S. Rault, M. Severicourt, K.M. Hassan, and M. Robba Tetrahedron Lett. 27 1986 2607
25. Y. Inubushi, T. Kikuchi, T. Ibuka, K. Tanaka, I. Saji, and K. Tokane J. Chem. Soc., Chem. Commun. 1972 1252
26. M.R. Paleo, D. Dominguez, and L. Castedo Tetrahedron Lett. 34 1993 2369
27. H.D. Dakin, and R. West J. Biol. Chem. 78 1928 745
28. H.D. Dakin, and R. West J. Biol. Chem. 78 1928 91
29. H.D. Dakin, and R. West J. Biol. Chem. 78 1928 757
30. Lewis acids: B. Bhatia, M.M. Reddy, and J. Iqbal J. Chem. Soc., Chem. Commun. 1994 713
31. D. Bahulayan, S.K. Das, and J. Iqbal J. Org. Chem. 68 2003 5735
32. R. Ghosh, S. Maity, and A. Chakraborty Synlett 2005 115
33. R. Ghosh, S. Maity, and A. Chakraborty Tetrahedron 62 2006 4059
34. E. Rafiee, F. Shahbazi, M. Joshaghani, and F. Tork J. Mol. Catal. A: Chem. 242 2005 129 134
35. G. Pandey, R.P. Singh, A. Garg, and V.K. Singh Tetrahedron Lett. 46 2005 2137
36. A. Khan, T. Parvin, and L.H. Choudhury Tetrahedron 63 2007 5593
37. M.T. Maghsoodlou, A. Hassankhani, H.R. Shaterian, S.M. Khorasani, and E. Mosaddegh Tetrahedron Lett. 48 2007 1729
38. L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri, and V. Kumari J. Mol. Catal. A: Chem. 264 2007 22
39. B. Das, and K.R. Reddy Helv. Chim. Acta 89 2006 3109
40. A.T. Khan, L.H. Choudhury, T. Parvin, and M. Asif-Ali Tetrahedron Lett. 47 2006 8137
41. E.N. Prabhakaran, and J. Iqbal J. Org. Chem. 64 1999 3339
42. T.A. Salama, S.S. Elmorsy, A.G.M. Khalil, and M.A. Ismail Tetrahedron Lett. 48 2007 6199
43. J.S. Yadav, B.V.S. Reddy, K.S. Shankar, and K. Premalatha Org. Commun. 4 2008 76
44. H. Mao, J. Wan, and Y. Pan Tetrahedron 65 2009 1026
45. Protic/Brnsted acids: B. Das, K.R. Reddy, Y. Srinivas, and R.A. Kumar Can. J. Chem. 85 2007 479
46. H.R. Shaterian, H. Yarahmadi, and M. Ghashang ARKIVOC xvi 2007 298 313
47. T. Yakaiah, B.V.P. Lingaiah, V.G. Reddy, B. Narsaiah, and P.S. Rao ARKIVOC xiii 2007 227
48. M.M. Heravi, L. Ranjbar, F. Derikvand, and F.F. Bamoharramb J. Mol. Catal. A: Chem. 276 2007 226
49. T. Yakaiah, G.V. Reddy, B.P.V. Lingaiah, B. Narsaiah, and P.S. Rao Synth. Commun. 35 2005 1307
50. H.R. Shaterian, A. Hosseinian, and M. Ghashang Synth. Commun. 38 2008 3766
51. A.R. Momeni, and M. Sadeghi Appl. Catal., Gen. 357 2009 100
52. M.A. Pasa, V.P. Jayashankara, and N. Ramachandraswamy Synth. Commun. 37 2007 1551
53. A. Hassankhani, M.T. Maghsoodlou, S.M. Habibi-Khorassani, H. Hosseini-mahdiabad, and G. Marandi ARKIVOC ii 2008 134
54. S.K. Garg, R. Kumar, and A.K. Chakraborti Synlett 2005 1370
55. R. Kumar, R. Thilagavathi, R. Gulhane, and A.K. Chakraborti J. Mol. Catal. A: Chem. 250 2006 227
56. B. Shivani Pujala, and A.K. Chakraborti J. Org. Chem. 72 2007 3713
57. R. Dalpozzo, G. Bartoli, L. Sambri, and P. Melchiorre Chem. Rev. 110 2010 3501
58. J. Escribano, F. Gracia-Canovas, and F. Gracia-Carmona Biochem. J. 1254 1988 829
59. Y. Takano, K. Hase-Aoki, H. Horiuchi, L. Zhao, Y. Kasahara, S. Kondo, and M.A. Becker Life Sci. 76 2005 1835
60. L. Kuraka, T. Kalnovicova, B. Lia, and P. Turanil Clin. Chem. 42 1996 756
61. S. Watanabe, Y. Kimura, K. Shindo, and T. Fukui J. Health Sci. 52 2006 738
62. GOLD, evaluation version 4.0.1. Cambridge Crystallographic Data Centre: Cambridge, U.K. 2009.
63. C. Enroth, B.T. Eger, K. Okamoto, T. Nishino, and E.F. Pai Proc. Natl. Acad. Sci. U.S.A. 97 2000 10723
64. S.K. Burley, and G.A. Petsko Science 229 1985 23
65. It may be mentioned that perchlorates are potentially explosive when heated in the presence of combustible substances at high temperature; J.C. Schumacher, Perchlorates - Their Properties, Manufacture and Uses; ACS Monograph Series, Reinhold: New York, 1960. However the reaction conditions reported in the present paper do not involve the harsh conditions such as heating.
66. ChemDraw Ultra 6.0 and Chem3D Ultra, Cambridge Soft Corporation, Cambridge, USA.
67. See Supplementary data.