Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

DARU, Journal of Pharmaceutical Sciences

Volumn 20, Issue 1, 2012, Pages

  Mohammadhosseini, Negar ^a,b   Alipanahi, Zahra ^a   Alipour, Eskandar ^a   Emami, Saeed ^c   Faramarzi, Mohammad Ali ^b   Samadi, Nasrin ^b   Khoshnevis, Nika ^b   Shafiee, Abbass ^b   Foroumadi, Alireza ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Antibacterial activity; Levofloxacin; Oximes; Quinolones; Thiophene derivatives

Indexed keywords

10 [4 [2 (5 BROMOTHIOPHEN 2 YL) 2 OXOETHYL)PIPERAZIN 1 YL) 9 FLUORO 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 10 [4 [2 (5 CHLOROTHIOPHEN 2 YL) 2 (METHOXYIMINO)ETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 10 [4 [2 (5 CHLOROTHIOPHEN 2 YL) 2 OXOETHYL)PIPERAZIN 1 YL) 9 FLUORO 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 10 [4 [2 (BENZYLOXYIMINO) 2 (5 CHLOROTHIOPHEN 2 YL)ETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO [2, 3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 10 [4 [2 (BENZYLOXYIMINO) 2 (THIOPHEN 2 YL)ETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 9 FLUORO 10 [4 [2 (BENZYLOXYIMINO) 2 (THIOPHEN 3 YL)ETHYL]PIPERAZIN 1 YL] 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 9 FLUORO 10 [4 [2 (HYDROXYIMINO) 2 (THIOPHEN 2 YL)ETHYL]PIPERAZIN 1 YL] 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 9 FLUORO 10 [4 [2 (HYDROXYIMINO) 2 (THIOPHEN 3 YL)ETHYL]PIPERAZIN 1 YL] 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 9 FLUORO 10 [4 [2 (METHOXYIMINO) 2 (THIOPHEN 2 YL)ETHYL]PIPERAZIN 1 YL] 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; 9 FLUORO 10 [4 [2 (METHOXYIMINO) 2 (THIOPHEN 3 YL)ETHYL]PIPERAZIN 1 YL] 3 METHYL 7 OXO 3,7 DIHYDRO 2H [1,4]OXAZINO[2,3,4 IJ]QUINOLINE 6 CARBOXYLIC ACID; ANTIBIOTIC AGENT; CIPROFLOXACIN; LEVOFLOXACIN; NORFLOXACIN; OFLOXACIN; OXIME DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84870429571     PISSN: 15608115     EISSN: 20082231     Source Type: Journal    
DOI: 10.1186/2008-2231-20-16     Document Type: Article

References (18)

1. Synthesis, characterization, antibacterial activity, and interaction with DNA of the vanadyl-enrofloxacin complex. Efthimiadou EK, Katsaros N, Karaliota A, Psomas G, Bioorg Med Chem Lett 2007 17 1238 1242 10.1016/j.bmcl.2006.12.032 17196389
2. Structural features of new quinolones and relationship to antibacterial activity against Gram-positive bacteria. Emami S, Shafiee A, Foroumadi A, Mini Rev Med Chem 2006 6 375 386 10.2174/138955706776361493 16613574
3. Adverse reactions to fluoroquinolones. An overview on mechanistic aspects. Sarro AD, Sarro GD, Curr Med Chem 2001 8 371 384 10.2174/ 0929867013373435 11172695
4. Type II topoisomerases as targets for quinolone antibacterials. Anderson VE, Osheroff N, Curr Pharm Des 2001 7 339 355
5. Synthesis, antibacterial, and cytotoxic evaluation of certain 7-substituted norfloxacin derivatives. Fang KC, Chen YL, Sheu JY, Wang TC, Tzeng CC, J Med Chem 2000 43 3809 3812 10.1021/jm000153x 11020298
6. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases. Pandeya SN, Sriram DV, Nath G, DeClercq E, Eur J Med Chem 2000 35 249 255 10.1016/S0223-5234(00)00125-2 10758286 (Pubitemid 30165688)
7. Structure-activity and structure-side-effect relationships for the quinolone antibacterials. Domagala MJ, Antimicrob Chemother 1994 33 685 706 10.1093/jac/33.4.685
8. Synthesis and biological testing of non-fluorinated analogues of levofloxacin. Jeffrey LJ, Almstead JK, Gallagher CP, Hu XE, Kim NK, Taylor CJ, Twinem TL, Cynthia D, Bioorg Med Chem Lett 2003 13 2373 2375 10.1016/S0960-894X(03)00399-8 12824037 (Pubitemid 36724985)
9. Bactericidal activity of levofloxacin and ciprofloxacin on clinical isolates of different phenotypes of Pseudomonas aeruginosa. Segatore B, Setacci D, Perilli M, Franceschini N, Marchetti F, Amicosante G, Int J Antimicrob Agents 2000 13 223 226 10.1016/S0924-8579(99)00119-3 10724029
10. Synthesis and antibacterial activity of new 7-piperazinylquinolones containing a functionalized 2-(furan-3-yl)ethyl moiety. Foroumadi A, Mohammadhosseini N, Emami S, Letafat B, Faramarzi MA, Samadi N, Shafiee A, Arch Pharm 2007 340 47 52 10.1002/ardp.200600169 (Pubitemid 46154835)
11. Synthesis and antibacterial activity of new N-(phenethyl)piperazine moiety. Foroumadi A, Ghodsi S, Emami S, Najjari S, Samadi N, Faramarzi MA, Beikmohammadi L, Shirazi FH, Shafiee A, Bioorg Med Chem Lett 2006 16 3499 3503 10.1016/j.bmcl.2006.03.103 16644219 (Pubitemid 43777121)
12. Synthesis and antibacterial activity of new N-[2-(thiophen-3-yl)ethyl] piperazinyl quinolones. Letafat B, Emami S, Mohammadhoseini N, Faramarzi MA, Samadi N, Shafiee A, Foroumadi A, Chem Pharm Bull 2007 55 894 898 10.1248/cpb.55.894 17541188 (Pubitemid 46890089)
13. Synthesis and antibacterial activity of quinolone-based compounds containing a coumarin moiety. Emami S, Foroumadi A, Faramarzi MA, Samadi N, Arch Pharm 2008 341 42 48 10.1002/ardp.200700090 (Pubitemid 351211812)
14. Synthesis and in-vitro antibacterial activity of N-piperazinyl quinolone derivatives with 5-chloro-2-thienyl group. Shafiee A, Haddad Zahmatkesh M, Mohammadhosseini N, Khalafy J, Emami S, Moshafi MH, Sorkhi M, Foroumadi A, Daru 2008 16 189 195
15. Synthesis and antibacterial activity of levofloxacin derivatives with certain bulky residues on piperazine ring. Foroumadi A, Emami S, Mansouri S, Javidnia A, Saeid-Adeli N, Shirazi FH, Shafiee A, Eur J Med Chem 2007 42 985 992 10.1016/j.ejmech.2006.12.034 17316916 (Pubitemid 46907340)
16. Synthesis and in-vitro antibacterial activities of N-substituted piperazinyl quinolones. Foroumadi A, Emami S, Davood A, Moshafi MH, Sharifian A, Tabatabaiee M, Tarhimi Farimani H, Sepehri G, Shafiee A, Arch Pharm 1997 3 559 563 (Pubitemid 28067718)
17. Synthesis and antibacterial activities of optically active ofloxacin and its fluoromethyl derivative. Atarashi S, Yokohama S, Yamazaki KI, Sakano KI, Imamura M, Chem Pharm Bull 1987 35 1896 1902 10.1248/cpb.35.1896 3664798
18. Baron EJ, Finegold SM, Bailey Scotts Diagnostic Microbiology The C. V. Mosby Company, St. Louis 11 2002 235 236 22931315