A convergent construction of 1,4-dihydropyridine scaffold containing indole fragment

Tetrahedron

Volumn 67, Issue 30, 2011, Pages 5469-5476

  Chen, Tao ^a   Xu, Xiao Ping ^a   Liu, Hai Feng ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Hexahydroquinoline dihydropyridine derivatives; Indole; Multi component reaction; One pot

Indexed keywords

1,4 DIHYDROPYRIDINE; ALDEHYDE DERIVATIVE; AMMONIUM ACETATE; BENZOQUINONE DERIVATIVE; INDOL 3 YL 1,4 DIHYDROPYRIDINE DERIVATIVE; INDOL 3 YL 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79959328976     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.065     Document Type: Article

References (76)

1. T. Godfraid, R. Miller, and M. Wibo Pharmacol. Rev. 38 1986 321
2. P.P. Mager, R.A. Coburn, A.J. Solo, D.J. Triggle, and H. Rothe Drug Des. Discovery 8 1992 273
3. R. Mannhold, B. Jablonka, W. Voigdt, K. Schoenafinger, and K. Schravan Eur. J. Med. Chem. 27 1992 229
4. D.J. Triggle, D.D. Langs, and R.A. Janis Med. Res. Rev. 9 1989 123
5. O. Aruoma, C. Smith, R. Cecchini, P. Evans, and B. Halliwell Biochem. Pharmacol. 1991 42
6. A. Hilgeroth Mini-Rev. Med. Chem. 2 2002 235
7. M. Kawase, A. Shah, H. Gaveriya, N. Motohashi, H. Sakagami, A. Varga, and J. Molnar Bioorg. Med. Chem. 10 2002 1051
8. R.A. Janis, and D.J. Triggle J. Med. Chem. 26 1983 775
9. B. Loev, M.M. Goodman, K.M. Snader, R. Tedeschi, and E. Macko J. Med. Chem. 17 1974 956
10. U. Rose, and M. Dräger J. Med. Chem. 35 1992 2238
11. A. Kumar, S. Sharma, V.D. Tripathi, R.A. Maurya, S.P. Srivastava, G. Bhatia, A.K. Tamrakar, and A.K. Srivastava Bioorg. Med. Chem. 18 2010 4138
12. K.K. Pasunooti, C. Nixon Jensen, H. Chai, M.L. Leow, D.-W. Zhang, and X.-W. Liu J. Comb. Chem. 12 2010 577
13. C.-S. Yao, C.-H. Wang, B. Jiang, and S.-J. Tu J. Comb. Chem. 12 2010 472
14. A. Heydari, S. Khaksar, M. Tajbakhsh, and H.R. Bijanzadeh J. Fluorine Chem. 130 2009 609
15. C.G. Evans, and J.E. Gestwicki Org. Lett. 11 2009 2957
16. W.K. Su, J. Li, and J.J. Li Aust. J. Chem. 61 2008 860
17. B. Buelbuel, G.S. Oztuerk, M. Vural, R. Simsek, Y. Sarioglu, A. Linden, M. Ulgen, and C. Safak Eur. J. Med. Chem. 44 2009 2052
18. R.A. Mekheimer, A.A. Hameed, and K.U. Sadek Green Chem. 10 2008 592
19. S.-J. Tu, S. Yan, X.-D. Cao, S.-S. Wu, X.-H. Zhang, W.-J. Hao, Z.-G. Han, and F. Shi J. Organomet. Chem. 694 2009 91
20. S.B. Sapkal, K.F. Shelke, B.B. Shingate, and M.S. Shingare Tetrahedron Lett. 50 2009 1754
21. A. Kumar, and R.A. Maurya Synlett 6 2008 883
22. S. Kumar, P. Sharma, K.K. Kapoor, and M.S. Hundal Tetrahedron 64 2008 536
23. A. Kumar, and R.A. Maurya Tetrahedron 63 2007 1946
24. J.C. Legeay, J.Y. Goujon, J.J. Vanden Eynde, L. Toupet, and J.P. Bazureau J. Comb. Chem. 8 2006 829
25. S.K. Ko, and C.-F. Yao Tetrahedron 62 2006 7293
26. L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian, and C.-T. Qian Tetrahedron 61 2005 1539
27. S.-J. Ji, Z.-Q. Jiang, J. Lu, and T.-P. Loh Synlett 2004 831
28. G.-W. Wang, and C.B. Miao Green Chem. 8 2006 1080
29. C.-S. Jia, Z. Zhang, S.-J. Tu, and G.-W. Wang Org. Biomol. Chem. 4 2006 104
30. Z.B. Huang, Y. Hu, Y. Zhou, and D.Q. Shi; ACS Comb. Sci. 13 2011 45
31. X.-S. Wang, M.-M. Zhang, Z.-S. Zeng, D.-Q. Shi, S.-J. Tu, X.-Y. Wei, and Z.-M. Zong Tetrahedron Lett. 46 2005 7169
32. X.-S. Wang, M.-M. Zhang, H. Jiang, C.-S. Yao, and S.-J. Tu Tetrahedron 63 2007 4439
33. M. Dabiri, M. Bahramnejad, and M. Baghbanzadeh Tetrahedron 65 2009 9443
34. S.-J. Tu, S.S. Wu, S. Yan, W.J. Hao, X.H. Zhang, X.D. Cao, Z.G. Han, B. Jiang, F. Shi, M. Xia, and J.F. Zhou J. Comb. Chem. 11 2009 239
35. For recent examples see:
36. P.R. Kym, M.E. Kort, M.J. Coghlan, J.L. Moore, R. Tang, J.D. Ratajczyk, D.P. Larson, S.W. Elmore, J.K. Pratt, M.A. Stashko, H.D. Falls, C.W. Lin, M. Nakane, L. Miller, C.M. Tyree, J.N. Miner, P.B. Jacobson, D.M. Wilcox, P. Nguyen, and B.C. Lane J. Med. Chem. 46 2003 1016
37. H. Heitsch Curr. Med. Chem. 9 2002 913
38. A. Nayyar, A. Malde, R. Jain, and E. Coutinho Bioorg. Med. Chem. 14 2006 847
39. P. Narender, U. Srinivas, M. Ravinder, B.A. Rao, C. Ramesh, K. Harakishore, B. Gangadasu, U.S.N. Murthy, and V.J. Rao Bioorg. Med. Chem. 14 2006 4600
40. N. Muruganantham, R. Sivakumar, N. Anbalagan, V. Gunasekaran, and J.T. Leonard Biol. Pharm. Bull. 27 2004 1683
41. A. Tsotinis, M. Vlachou, S. Zouroudis, A. Jeney, F. Timar, D.E. Thurston, and C. Roussakis Lett. Drug Des. Discovery 2 2005 189
42. A.A. Joshi, and C.L. Viswanathan Bioorg. Med. Chem. Lett. 16 2006 2613
43. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045
44. W.N. Xiong, C.G. Yang, and B. Jiang Bioorg. Med. Chem. 9 2001 1773
45. R.J. Sundberg The Chemistry of Indoles 1996 Academic New York, NY
46. A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio J. Nat. Prod. 63 2000 447
47. B. Bao, Q. Sun, X. Yao, J. Hong, C.O. Lee, C.J. Sim, K.S. Im, and J.H. Jung J. Nat. Prod. 68 2005 711
48. E.B. Skibo, C. Xing, and R.T. Dorr J. Med. Chem. 44 2001 3545
49. L. Gupta, A. Talwar, N.S. Palne, S. Gupta, and P.M.S. Chauhan Bioorg. Med. Chem. Lett. 17 2007 4075
50. K. Kaniwa, M.A. Arai, X. Li, and M. Ishibashi Bioorg. Med. Chem. Lett. 17 2007 4254
51. S. Sakemi, and H.H. Sun J. Org. Chem. 56 1991 4304
52. I. Kawasaki, M. Yamashita, and S. Ohta Chem. Pharm. Bull. 44 1996 1831
53. T. Kouko, K. Matsumura, and T. Kawasaki Tetrahedron 61 2005 2309
54. K. Higuchi, R. Takei, T. Kouko, and T. Kawasaki Synthesis 2007 669
55. B. Jiang, C.-G. Yang, W.-N. Xiong, and J. Wang Bioorg. Med. Chem. 9 2001 1149
56. M. Gompel, M. Leost, E.B.K. Joffé, L. Puricelli, L.H. Franco, J. Palermo, and L. Meijer Bioorg. Med. Chem. Lett. 14 2004 1703
57. P.A. Wender, S.T. Handy, and D.L. Wright Chem. Ind. 1997 765
58. B.M. Trost Angew. Chem., Int. Ed. Engl. 34 1995 259
59. L. Weber, K. Illgen, and M. Almstetter Synlett 1999 366
60. H. Bienaymé, C. Hulme, G. Oddon, and P. Schmitt Chem. - Eur. J. 6 2000 3321
61. N.K. Terrett Combinatorial Chemistry 1998 Oxford University New York, NY
62. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. Engl. 32 1993 131
63. A. Domling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
64. S.-J. Ji, and S.-Y. Wang Synlett 2003 2074
65. S.-J. Ji, S.-Y. Wang, Y. Zhang, and T.-P. Loh Tetrahedron 60 2004 2051
66. D.-G. Gu, S.-J. Ji, Z.-Q. Jiang, M.-F. Zhou, and T.-P. Loh Synlett 2005 959
67. S.-Y. Wang, and S.-J. Ji Tetrahedron 62 2006 1527
68. C. Sun, S.-J. Ji, and Y. Liu Tetrahedron Lett. 48 2007 8987
69. S.-Y. Wang, and S.-J. Ji Synlett 2007 2222
70. S.-L. Zhu, S.-J. Ji, and Y. Zhang Tetrahedron 63 2007 9365
71. S.-L. Zhu, S.-J. Ji, X.-M. Su, C. Sun, and Y. Liu Tetrahedron Lett. 49 2008 1777
72. S.-L. Zhu, S.-J. Ji, K. Zhao, and Y. Liu Tetrahedron Lett. 49 2008 2578
73. K. Zhao, X.-P. Xu, S.-L. Zhu, D.-Q. Shi, Y. Zhang, and S.-J. Ji Synthesis 2009 2697
74. K. Zhao, S.-L. Zhu, D.-Q. Shi, Y. Zhang, X.-P. Xu, and S.-J. Ji Synthesis 2010 1793
75. T. Chen, X.-P. Xu, and S.-J. Ji J. Comb. Chem. 12 2010 659
76. C.W. Mosher, H.Y. Wu, A.N. Fujiwara, and E.M. Acton J. Med. Chem. 25 1982 18