Synthesis and antibacterial activity of levofloxacin derivatives with certain bulky residues on piperazine ring

European Journal of Medicinal Chemistry

Volumn 42, Issue 7, 2007, Pages 985-992

  Foroumadi, Alireza ^a   Emami, Saeed ^b   Mansouri, Shahla ^c   Javidnia, Azita ^a   Saeid Adeli, Nosratollah ^c   Shirazi, Farshad H ^d   Shafiee, Abbas ^a  

^a Tehran University of Medical Science   (Iran)

^b MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

In vitro antibacterial activity; Levofloxacin derivatives; Quinolones

Indexed keywords

10 [4 (2 (2,4 DICHLOROPHENYL) 2 HYDROXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 (4 BROMOPHENYL) 2 HYDROXYIMINOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 (4 CHLOROPHENYL) 2 HYDROXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 (4 FLUOROPHENYL) 2 HYDROXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 (4 METHOXYPHENYL) 2 HYDROXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 (4 METHYLPHENYL) 2 HYDROXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 PHENYL 2 HYDROXYIMINOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 PHENYL 2 OXOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 (2 PHENYL 2 PHENYLMETHOXYIMINOETHYL)PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 [2 (2,4 DICHLOROPHENYL) 2 OXOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 [2 (4 BROMOPHENYL) 2 OXOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 [2 (4 CHLOROPHENYL) 2 OXOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 [2 (4 FLUOROPHENYL) 2 OXOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; 10 [4 [2 (4 METHOXYPHENYL) 2 OXOETHYL]PIPERAZIN 1 YL] 9 FLUORO 3 METHYL 7 OXO 2,3 DIHYDRO 7H PYRIDO[1,2,3 DE][1,4]BENZOXAZINE 6 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CIPROFLOXACIN; CISPLATIN; ENOXACIN; ETOPOSIDE; LEVOFLOXACIN; NORFLOXACIN; OFLOXACIN; PIPERAZINE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HUMAN; HUMAN CELL; STREPTOCOCCUS INFECTION;

ANTI-BACTERIAL AGENTS; MOLECULAR STRUCTURE; OFLOXACIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34250160897     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.12.034     Document Type: Article

References (19)

1. Coleman K. Drug Discov. Today Ther. Strateg. 1 (2004) 455-460
2. Johnson A.P., Livermore D.M., and Tillotson G.S. J. Hosp. Infec. 49 Suppl. A (2001) S3-S11
3. Emami S., Shafiee A., and Foroumadi A. Mini Rev. Med. Chem. 6 (2006) 375-386
4. Lescher G.Y., Froelich E.J., Gruett M.D., Bailey J.H., and Brundage R.P. J. Med. Pharm. Chem. 91 (1962) 1063-1065
5. Hooper D.C. Drugs 58 Suppl. 2 (1999) 6-10
6. Atarashi S., Yokohama S., Yamazaki K.-I., Sakano K.-I., and Imamura M. Chem. Pharm. Bull. 35 (1987) 1896-1902
7. Mitscher L.A., Sharma P.N., Chu D.T.W., Shen L.L., and Pernet A.G. J. Med. Chem. 30 (1987) 2283-2286
8. Morrissey I., Hoshino K., Sato K., Yoshida A., Hayakawa I., Bures M.G., and Shen L.L. Antimicrob. Agents Chemother. 40 (1996) 1775-1784
9. Coyle E.A., Kaatz G.W., and Rybak M.J. Antimicrob. Agents Chemother. 45 (2001) 1654-1659
10. Foroumadi A., Emami S., Davood A., Moshafi M.H., Sharifian A., Tabatabaiee M., Tarhimi Farimani H., Sepehri G., and Shafiee A. Pharm. Sci. 3 (1997) 559-563
11. Foroumadi A., Soltani F., Emami S., and Davood A. Boll. Chim. Farm. 141 (2002) 247-249
12. Mirzaei M., and Foroumadi A. Pharm. Pharmacol. Commun. 6 (2000) 351-354
13. Foroumadi A., Emami S., Mehni M., Moshafi M.H., and Shafiee A. Bioorg. Med. Chem. Lett. 15 (2005) 4536-4539
14. Foroumadi A., Oboudiat M., Emami S., Karimollah A., Saghaee L., Moshafi M.H., and Shafiee A. Bioorg. Med. Chem. 14 (2006) 3421-3427
15. Foroumadi A., Ghodsi S., Emami S., Najjari S., Samadi N., Faramarzi M.A., Beikmohammadi L., Shirazi F.H., and Shafiee A. Bioorg. Med. Chem. Lett. 16 (2006) 3499-3503
16. Baron E.J., and Finegold S.M. Bailey and Scott's Diagnostic Microbiology. eighth ed. (1990), C.V. Mosby, St Louis pp. 184-188
17. Sissi C., and Palumbo M. Curr. Med. Chem. Anti-Cancer Agents 3 (2003) 439-450
18. Mosmann T. J. Immunol. Methods 65 (1983) 55-63
19. Anderson V.E., and Osheroff N. Curr. Pharm. Design 7 (2001) 339-353