Synthesis of naphthyridone derivatives containing 8-alkoxyimino-1,6- dizaspiro[3.4]octane scaffolds

Tetrahedron

Volumn 67, Issue 43, 2011, Pages 8264-8270

  Feng, Lian Shun ^a   Liu, Ming Liang ^a   Wang, Shuo ^a   Chai, Yun ^a   Lv, Kai ^a   Shan, Guang Zhi ^a   Cao, Jue ^a   Li, Su Jie ^a   Guo, Hui Yuan ^a  

^a INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

8 Alkoxyimino 1,6 dizaspiro 3.4 octane scaffolds; Naphthyridone derivatives; Synthesis

Indexed keywords

1 (PYRIDIN 3 YL) 6 FLUORO 7 (1 METHYL 8 (METHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1 (PYRIDIN 3 YL) 6 FLUORO 7(1 METHYL 8 (ETHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7(8 (ETHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7(8 (METHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 7(8 (METHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1 ETHYL 6 FLUORO 7(8 (METHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1(2,4 DIFLUOROPHENYL) 6 FLUORO 7 (8 (ETHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1(2,4 DIFLUOROPHENYL) 6 FLUORO 7(8 (METHOXYIMINO) 1,6 DIAZOSPIRO [3 4] OCT 6 YL) 4 OXO 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 8 ALKOXYIMINO 1,6 DIZASPIRO [3 4] OCTANE; CARBAMIC ACID ESTER; CARBOXYLIC ACID DERIVATIVE; MOLECULAR SCAFFOLD; NAPHTHYRIDINE DERIVATIVE; NAPHTHYRIDONE DERIVATIVE; POTASSIUM CARBONATE; TERT BUTYL 3 CYANO 4 OXOPYRROLIDINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; ZABOFLOXACIN;

ARTICLE; CHEMICAL STRUCTURE; METHYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 80053051312     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.08.089     Document Type: Article

References (27)

1. G.Y. Lesher, E.J. Froelich, M.D. Gruett, J.H. Bailey, and R.P. Brungaje J. Med. Pharm. Chem. 5 1962 1063 1068
2. D.C. Hooper, and E. Rubinstein Quinolone Antimicrobial Agents 3rd ed. 2003 ASM Washington DC
3. A.M. Emmerson, and A.M. Jones J. Antimicrob. Chemother. 51 2003 13 20
4. C. Mugnaini, S. Pasquini, and F. Corelli Curr. Med. Chem. 16 2009 1746 1767
5. K. Kaur, M. Jain, R.P. Reddy, and R. Jain Eur. J. Med. Chem. 45 2010 3245 3264
6. A. Bryskier, and J.F. Chantot Drugs 49 1995 16 28
7. H. Koga, A. Itoh, S. Murayama, S. Suzue, and T. Irikura J. Med. Chem. 23 1980 1358 1363
8. J.M. Domagala J. Antimicrob. Chemother. 33 1994 685 706
9. Z. Dang, Y.S. Yang, R.Y. Ji, and S.H. Zhang Bioorg. Med. Chem. Lett. 17 2007 4523 4526
10. W.R. Pitt, D.M. Parry, D.G. Perry, and C.R. Groom J. Med. Chem. 52 2009 2952 2963
11. R.R.R. Taylor, H.C. Twin, W.W. Wen, R.J. Mallot, A.J. Lough, S.D. Gray-Owen, and R.A. Batey Tetrahedron 66 2010 3370 3377
12. C.V. Kavitha, S.L. Gaonkar, J.N.N.S. Chandra, C.T. Sadashiva, and K.S. Rangappa Bioorg. Med. Chem. 15 2007 7391 7398
13. D. Milatovic, F.J. Schmitz, S. Brisse, J. Verhoef, and A.C. Fluit Antimicrob. Agents Chemother. 44 2000 1102 1107
14. C. Clark, K. Smith, L. Ednie, T. Bogdanovich, B. Dewasse, P. McGhee, and P.C. Appelbaum Antimicrob. Agents Chemother. 52 2008 77 84
15. R.N. Jones, T.R. Fritsche, and H.S. Sader Antimicrob. Agents Chemother. 52 2008 3763 3775
16. M.P. Gleeson J. Med. Chem. 51 2008 817 834
17. R.N. Jones, D.J. Biedenbach, P.G. Ambrose, and M.A. Wikler Diagn. Microbiol. Infect. Dis. 62 2008 110 112
18. C.Y. Hong, Y.K. Kim, J.H. Chang, S.H. Kim, H. Choi, D.H. Nam, Y.Z. Kim, and J.H. Kwak J. Med. Chem. 40 1997 3584 3593
19. M.L. Liu, L.Y. Sun, Y.G. Wei, and H.Y. Guo Chin. J. Pharm. 34 2003 157 158
20. Q. Guo, L.S. Feng, M.L. Liu, Y.B. Zhang, Y. Chai, K. Lv, H.Y. Guo, and L.Y. Han Eur. J. Med. Chem. 45 2010 5498 5506
21. Y. Chai, M.L. Liu, B. Wang, Q. Guo, L.S. Feng, Y.B. Zhang, J. Cao, and H.Y. Guo Bioorg. Med. Chem. Lett. 20 2010 5195 5198
22. Y.B. Zhang, M.L. Liu, L.S. Feng, X.F. You, Q. Guo, and H.Y. Guo Arch. Pharm. Chem. Life Sci. 343 2010 143 151
23. Y.B. Zhang, J.X. Wang, M.L. Liu, B. Wang, Y. Chai, S.J. Li, and H.Y. Guo Eur. J. Med. Chem. 46 2011 2421 2426
24. D. Ben-Ishai, and A. Berger J. Org. Chem. 17 1952 1564 1570
25. G.A. Olah, S.C. Narang, B.G.B. Gupta, and E. Malhotra Synthesis 1 1979 61 62
26. T.L. Ho, and C.M. Wong Synth. Commun. 5 1975 305 307
27. Y.B. Zhang, G.Q. Li, M.L. Liu, X.F. You, L.S. Feng, K. Lv, J. Cao, and H.Y. Guo Bioorg. Med. Chem. Lett. 21 2011 928 931