Synthesis of benzo[3,4]azepino[1,2-b]isoquinolin-9-ones from 3-arylisoquinolines via ring closing metathesis and evaluation of topoisomerase i inhibitory activity, cytotoxicity and docking study

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5311-5320

  Van, Hue Thi My ^a,e   Khadka, Daulat Bikram ^a   Yang, Su Hui ^a   Le, Thanh Nguyen ^a,f   Cho, Suk Hee ^a   Zhao, Chao ^a   Lee, Ik Soo ^a   Kwon, Youngjoo ^b   Lee, Kyung Tae ^c   Kim, Yong Chul ^d   Cho, Won Jea ^a  

^a Chonnam National University   (South Korea)

^b Ewha Womans University   (South Korea)

^c Kyung Hee University   (South Korea)

^d Gwangju Institute of Science and Technology (GIST)   (South Korea)

^e HANOI UNIVERSITY OF PHARMACY   (Viet Nam)

^f GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Viet Nam)

Author keywords

3 Arylisoquinoline; Benzo 3,4 azepino 1,2 b isoquinolinone; Chemical shift difference; Docking study; Ring closing metathesis; Topoisomerase I

Indexed keywords

2 (2 ALLYL 1 OXO 1,2 DIHYDROISOQUINOLIN 3 YL) 4,5 DIMETHOXYBENZALDEHYDE; 2 (2 ALLYL 1 OXO 1,2 DIHYDROISOQUINOLIN 3 YL) 5 METHOXYBENZALDEHYDE; 2 ALLYL 3 (2 HYDROXYMETHYL 4 METHOXYPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (2 HYDROXYMETHYL 4,5 DIMETHOXYPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (4 METHOXY 2 METHOXYMETHOXYMETHYLPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (4 METHOXY 2 VINYLPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (4,5 DIMETHOXY 2 METHOXYMETHOXYMETHYLPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (4,5 DIMETHOXY 2 VINYLPHENYL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (6 HYDROXYMETHYLBENZO[1,3]DIOXOL 5 YL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 (6 HYDROXYMETHYLBENZO[1,3]DIOXOL 5 YL) 7,8 DIMETHOXYISOQUINOLIN 1(2H) ONE; 2 ALLYL 3 (6 VINYLBENZO[1,3]DIOXOL 5 YL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 3 [6 [(METHOXYMETHOXY)METHYL]BENZO[D][1,3]DIOXOL 5 YL]ISOQUINOLIN 1(2H) ONE; 2 ALLYL 7,8 DIMETHOXY 3 (6 METHOXYMETHOXYMETHYLBENZO[1,3]DIOXOL 5 YL) 2H ISOQUINOLIN 1 ONE; 2 ALLYL 7,8 DIMETHOXY 3 (6 VINYLBENZO[1,3]DIOXOL 5 YL) 2H ISOQUINOLIN 1 ONE; 3 (4 METHOXY 2 METHOXYMETHOXYMETHYLPHENYL) 2H ISOQUINOLIN 1 ONE; 3 (4,5 DIMETHOXY 2 METHOXYMETHOXYMETHYLPHENYL) 2H ISOQUINOLIN 1 ONE; 3 [5 [(METHOXYMETHOXY)METHYL]BENZO[D][1,3]DIOXOL 6 YL]ISOQUINOLIN 1(2H) ONE; 3 ARYLISOQUINOLINE DERIVATIVE; 3 METHOXY 7H BENZO[3,4]AZEPINO[1,2 B]ISOQUINOLIN 9 ONE; 4 METHOXY 2 METHOXYMETHOXYMETHYLBENZONITRILE; 4,5 DIMETHOXY 2 METHOXYMETHOXYMETHYLBENZONITRILE; 6 (2 ALLYL 1,2 DIHYDRO 1 OXOISOQUINOLIN 3 YL)BENZO[D][1,3]DIOXOLE 5 CARBALDEHYDE; 6 (2 ALLYL 1,2 DIHYDRO 7,8 DIMETHOXY 1 OXOISOQUINOLIN 3 YL)BENZO[D][1,3]DIOXOLE 5 CARBALDEHYDE; 6 METHOXYMETHOXYMETHYLBENZO[1,3]DIOXOLE 5 CARBONITRILE; 7,8 DIMETHOXY 3 (6 METHOXYMETHOXYMETHYLBENZO[1,3]DIOXOL 5 YL) 2H ISOQUINOLIN 1 ONE; BENZO[3,4]AZEPINO[1,2 B]ISOQUINOLIN 9 ONE DERIVATIVE; CAMPTOTHECIN; DNA TOPOISOMERASE; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTROPY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGEN BOND; MOLECULAR DOCKING; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BENZAZEPINES; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLIZATION; DNA TOPOISOMERASES, TYPE I; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE I INHIBITORS;

EID: 80052558216     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.08.006     Document Type: Article

References (48)

1. G. Damia, and M. D'Incalci Eur. J. Cancer 45 2009 2768
2. J.R. Pollard, and M. Mortimore J. Med. Chem. 52 2009 2629
3. A. Hassner, B. Amit, V. Marks, and H.E. Gottlieb J. Org. Chem. 68 2003 6853
4. M. Qadir, J. Cobb, P.W. Sheldrake, N. Whittall, A.J. White, K.K. Hii, P.N. Horton, and M.B. Hursthouse J. Org. Chem. 70 2005 1545
5. H. Tabata, H. Suzuki, K. Akiba, H. Takahashi, and H. Natsugari J. Org. Chem. 75 2010 5984
6. H.T. Van, Q.M. Le, K.Y. Lee, E.S. Lee, Y. Kwon, T.S. Kim, T.N. Le, S.H. Lee, and W.J. Cho Bioorg. Med. Chem. Lett. 17 2007 5763
7. W.J. Cho, Q.M. Le, H.T. My Van, K. Youl Lee, B.Y. Kang, E.S. Lee, S.K. Lee, and Y. Kwon Bioorg. Med. Chem. Lett. 17 2007 3531
8. H.T. Van, and W.J. Cho Bioorg. Med. Chem. Lett. 19 2009 2551
9. S.H. Lee, H.T. Van, S.H. Yang, K.T. Lee, Y. Kwon, and W.J. Cho Bioorg. Med. Chem. Lett. 19 2009 2444
10. T.N. Le, S.G. Gang, and W.J. Cho J. Org. Chem. 69 2004 2768
11. D.B. Khadka, and W.J. Cho Bioorg. Med. Chem. 19 2011 724
12. A. Morrell, M.S. Placzek, J.D. Steffen, S. Antony, K. Agama, Y. Pommier, and M. Cushman J. Med. Chem. 50 2007 2040
13. X. Xiao, S. Antony, Y. Pommier, and M. Cushman J. Med. Chem. 48 2005 3231
14. M. Cushman, M. Jayaraman, J.A. Vroman, A.K. Fukunaga, B.M. Fox, G. Kohlhagen, D. Strumberg, and Y. Pommier J. Med. Chem. 43 2000 3688
15. J.C. Wang Annu. Rev. Biochem. 65 1996 635
16. J.J. Champoux Annu. Rev. Biochem. 70 2001 369
17. J.C. Wang Nat. Rev. Mol. Cell Biol. 3 2002 430
18. N. Merabet, J. Dumond, B. Collinet, L. Van Baelinghem, N. Boggetto, S. Ongeri, F. Ressad, M. Reboud-Ravaux, and S. Sicsic J. Med. Chem. 47 2004 6392
19. H.T. Van, S.H. Yang, D.B. Khadka, Y.C. Kim, and W.J. Cho Tetrahedron 65 2009 10142
20. B. Alcaide, P. Almendros, and A. Luna Chem. Rev. 109 2009 3817
21. L. Vieille-Petit, X. Luan, M. Gatti, S. Blumentritt, A. Linden, H. Clavier, S.P. Nolan, and R. Dorta Chem. Commun. (Camb.) 2009 3783
22. G.C. Rudolf, A. Hamilton, A.G. Orpen, and G.R. Owen Chem. Commun. (Camb.) 2009 553
23. D. Benitez, E. Tkatchouk, and W.A. Goddard III Chem. Commun. (Camb.) 2008 6194
24. M.T. Mwangi, M.D. Schulz, and N.B. Bowden Org. Lett. 11 2009 33
25. J.H. Sohn, K.H. Kim, H.Y. Lee, Z.S. No, and H. Ihee J. Am. Chem. Soc. 130 2008 16506
26. V. Polshettiwar, and R.S. Varma J. Org. Chem. 73 2008 7417
27. D. Rix, F. Caijo, I. Laurent, F. Boeda, H. Clavier, S.P. Nolan, and M. Mauduit J. Org. Chem. 73 2008 4225
28. K. Vehlow, D. Wang, M.R. Buchmeiser, and S. Blechert Angew. Chem., Int. Ed. Engl. 47 2008 2615
29. S. Brass, H.D. Gerber, S. Dorr, and W.E. Diederich Tetrahedron 62 2006 1777
30. L. Delhaye, A. Merschaert, K. Diker, and I.N. Houpis Synthesis 2006 1437
31. D. Rix, F. Caijo, I. Laurent, L. Gulajski, K. Grela, and M. Mauduit Chem. Commun. (Camb.) 2007 3771
32. S.W. Chen, J.H. Kim, C.E. Song, and S.G. Lee Org. Lett. 9 2007 3845
33. C.E. Webster J. Am. Chem. Soc. 129 2007 7490
34. T.H. Le, S.G. Gang, and W.J. Cho Tetrahedron Lett. 45 2004 2763
35. T.N. Le, and W.J. Cho Chem. Pharm. Bull. (Tokyo) 53 2005 118
36. T.N. Le, and W.J. Cho Chem. Pharm. Bull. (Tokyo) 54 2006 476
37. T.N. Le, and W.J. Cho Bull. Korean Chem. Soc. 27 2006 2093
38. T.N. Le, and W.J. Cho Bull. Korean Chem. Soc. 28 2007 763
39. N. Le Thanh, H.T. Van, S.H. Lee, H.J. Choi, K.Y. Lee, B.Y. Kang, and W.J. Cho Arch. Pharm. Res. 31 2008 6
40. T.N. Le, and W.J. Cho Chem. Pharm. Bull. (Tokyo) 56 2008 1026
41. W.J. Cho, S.Y. Min, T.N. Le, and T.S. Kim Bioorg. Med. Chem. Lett. 13 2003 4451
42. G.J. Karabatsos, and G.C. Sonnichsen J. Am. Chem. Soc. 89 1967 5067
43. R.J. Abraham, M. Mobli, and R.J. Smith Magn. Reson. Chem. 41 2003 26
44. L.V. Rubinstein, R.H. Shoemaker, K.D. Paull, R.M. Simon, S. Tosini, P. Skehan, D.A. Scudiero, A. Monks, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1113
45. A. Basnet, P. Thapa, R. Karki, H. Choi, J.H. Choi, M. Yun, B.S. Jeong, Y. Jahng, Y. Na, W.J. Cho, Y. Kwon, C.S. Lee, and E.S. Lee Bioorg. Med. Chem. Lett. 20 2010 42
46. M. Facompre, C. Tardy, C. Bal-Mahieu, P. Colson, C. Perez, I. Manzanares, C. Cuevas, and C. Bailly Cancer Res. 63 2003 7392
47. W.J. Cho, M.J. Park, T. Imanishi, and B.H. Chung Chem. Pharm. Bull. (Tokyo) 47 1999 900
48. S.H. Cheon, J.S. Park, B.H. Chung, B.G. Choi, W.J. Cho, S.U. Choi, and C.O. Lee Arch. Pharm. Res. 21 1998 193