Conformationally constrained analogs of n-substituted piperazinylquinolones: Synthesis and antibacterial activity of n-(2,3-dihydro-4-hydroxyimino-4h-1-benzopyran-3-yl)-piperazinylquinolones

Archiv der Pharmazie

Volumn 342, Issue 7, 2009, Pages 405-411

  Emami, Saeed ^a,b   Foroumadi, Alireza ^c,d   Samadi, Nasrin ^c   Faramarzi, Mohammad A ^c   Rajabalian, Saeed ^d  

^a MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

2,3 Dihydro 4H 1 benzopyran; Antibacterial activity; Conformationally constrained analogs; Quinolones

Indexed keywords

1 CYCLOPROPYL 1,4 DIHYDRO 6 FLUORO 7 [4 (4 HYDROXYIMINO 2,3 DIHYDRO 4H 1 BENZOPYRAN 3 YL)PIPERAZIN 1 YL] 4 OXO 3 QUINOLINE CARBOXYLIC ACID; 1,4 DIHYDRO 1 ETHYL 6 FLUORO 7 [4 (4 HYDROXYIMINO 2,3 DIHYDRO 4H 1 BENZOPYRAN 3 YL)PIPERAZIN 1 YL] 4 OXO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; 1,4 DIHYDRO 1 ETHYL 6 FLUORO 7 [4 (4 HYDROXYIMINO 2,3 DIHYDRO 4H 1 BENZOPYRAN 3 YL)PIPERAZIN 1 YL] 4 OXO 3 QUINOLINE CARBOXYLIC ACID; 2,3 DIHYDRO 9 FLUORO 3 METHYL 10 [4 (4 HYDROXYIMINO 2,3 DIHYDRO 4H 1 BENZOPYRAN 3 YL)PIPERAZIN 1 YL] 7 OXO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; CIPROFLOXACIN; ENOXACIN; LEVOFLOXACIN; NORFLOXACIN; QUINOLINE DERIVED ANTIINFECTIVE AGENT; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTI-BACTERIAL AGENTS; CELL DEATH; DRUG DESIGN; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NIH 3T3 CELLS; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67650096788     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200800182     Document Type: Article

References (28)

1. G. H. Talbot, J. Bradley, J. E. Jr. Edwards, D. Gilbert, et al., Clin. Infect. Dis. 2006, 42, 657-668.
2. U. Theuretzbacher, J. H. Toney, Curr. Opin. Investig. Drugs 2006, 7, 158-166.
3. L. A. Mitscher, Chem. Rev. 2005, 105, 559-592.
4. M. V. N. de Souza, Mini Rev. Med. Chem. 2005, 5, 1009-1017.
5. D. C. Hooper, Clin. Infect. Dis. 2001, 32 (Suppl. 1), S9-S15.
6. J. S. Bakkan, Scand. J. Infect. Dis. 2004, 36, 85-92.
7. F. Baquero, J. Antimicrob. Chemother. 1997, 39, 1-6.
8. Y. C. Yee, C. A. Thornsberry, Antimicrob. Infect. Dis. Newslett. 1995, 14, 1-18.
9. T.-F. Ge, P. Y. P. Law, H. Y. Wong, Y.-Y. Ho, Eur. J. Pharmacol. 2007, 573, 70-74.
10. A. Graul, X. Rabasseda, J. Castaner, Drugs Future 1999, 24, 1324.
11. J. Kang, L. Wang, X.-L. Chen, D. J. Triggle, D. Rampe, Mol. Pharmacol. 2001, 59, 122-126.
12. R. C., Jr. Owens, Drugs 2004, 64, 1091-1124.
13. A. Bryskier, J. F. Chantot, Drugs 1995, 49 (Suppl. 2), 16-28.
14. P. C. Appelbaum, P. A. Hunter, Int. J. Antimicrob. Agents 2000, 16, 5-15.
15. S. Emami, A. Shafiee, A. Foroumadi, Mini Rev. Med. Chem. 2006, 6, 375-386.
16. S. Emami, A. Foroumadi, M. A. Faramarzi, N. Samadi, Arch. Pharm. Chem. Life Sci. 2008, 341, 42-48.
17. A. Foroumadi, S. Emami, A. Davood, M. H. Moshafi, et al., Pharmaceutical Sciences 1997, 3, 559-563.
18. A. Foroumadi, S. Ghodsi, S. Emami, S. Najjari, et al., Bioorg. Med. Chem. Lett. 2006, 16, 3499-3503.
19. A. Foroumadi, S. Emami, S. Mansouri, A. Javidnia, N. Saeid-Adeli, F. H. Shirazi, A. Shafiee, Eur. J. Med. Chem. 2007, 42, 985-992.
20. A. Foroumadi, N. Mohammadhosseini, S. Emami, B. Letafat, et al., Arch. Pharm. Chem. Life Sci. 2007, 340, 47-52.
21. B. Letafat, S. Emami, N. Mohammadhosseini, M. A. Faramarzi, et al., Chem. Pharm. Bull. 2007, 55, 894-898.
22. S. Emami, M. Falahati, A. Banifatemi, K. Moshiri, A. Shafiee, Arch. Pharm. Pharm. Med. Chem. 2002, 335, 318-324.
23. S. Emami, A. Shafiee, Tetrahedron 2005, 61, 2649-2654.
24. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution. Clinical Microbiology and Infection, Eucast Definitive Document E. Def 3.1, (2000) 6, pp. 509-515.
25. T. Mosmann, J. Immunol. Methods 1983, 65, 55-63.
26. S. Rajabalian, A. Foroumadi, A. Shafiee, S. Emami, J. Pharm. Pharmaceut. Sci. 2007, 10, 153-158.
27. V. Pliska in Lipophilicity in Drug Action and Toxicology, (Eds.: V. Pliska, B. Testa, H. van der Waterbeemd), Wiley-VCH, Weinheim, 1996, pp. 1-6.
28. A. Foroumadi, S. Mansouri, S. Emami, J. Mirzaei, et al., Arch. Pharm. Chem. Life Sci. 2006, 339, 621-624.