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Synthesis and in vitro antibacterial activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives.
Bioorg Med Chem Lett. 2011 Feb 01; 21(3):928-31.BM

Abstract

We report herein the design and synthesis of novel 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives based on the structures of new fluoroquinolones IMB and DZH. The antibacterial activity of these newly synthesized compounds was also evaluated and compared with gemifloxacin, ciprofloxacin, and levofloxacin. Results revealed that all of the target compounds 10-27 have good potency in inhibiting the growth of Staphylococcus aureus including MSSA (MIC: 0.125-8 μg/mL), Staphylococcus epidermidis including MRSE (MIC: 0.25-16 μg/mL), Streptococcus pneumoniae (MIC: 0.125-4 μg/mL), and Escherichia coli (MIC: 0.25-0.5 μg/mL). In particular, some compounds showed useful activity against several fluoroquinolone-resistant strains, and the most active compound 15 was found to be 16-128, 2-32, and 4-8-fold more potent than the three reference drugs against fluoroquinolone-resistant MSSA, MRSA, and MRSE.

Authors+Show Affiliations

Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, PR China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21232952

Citation

Zhang, Yibin, et al. "Synthesis and in Vitro Antibacterial Activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone Derivatives." Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 3, 2011, pp. 928-31.
Zhang Y, Li G, Liu M, et al. Synthesis and in vitro antibacterial activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives. Bioorg Med Chem Lett. 2011;21(3):928-31.
Zhang, Y., Li, G., Liu, M., You, X., Feng, L., Lv, K., Cao, J., & Guo, H. (2011). Synthesis and in vitro antibacterial activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives. Bioorganic & Medicinal Chemistry Letters, 21(3), 928-31. https://doi.org/10.1016/j.bmcl.2010.12.073
Zhang Y, et al. Synthesis and in Vitro Antibacterial Activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone Derivatives. Bioorg Med Chem Lett. 2011 Feb 1;21(3):928-31. PubMed PMID: 21232952.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and in vitro antibacterial activity of 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives. AU - Zhang,Yibin, AU - Li,Guoqing, AU - Liu,Mingliang, AU - You,Xuefu, AU - Feng,Lianshun, AU - Lv,Kai, AU - Cao,Jue, AU - Guo,Huiyuan, Y1 - 2010/12/19/ PY - 2010/10/19/received PY - 2010/12/14/revised PY - 2010/12/15/accepted PY - 2011/1/15/entrez PY - 2011/1/15/pubmed PY - 2011/5/3/medline SP - 928 EP - 31 JF - Bioorganic & medicinal chemistry letters JO - Bioorg. Med. Chem. Lett. VL - 21 IS - 3 N2 - We report herein the design and synthesis of novel 7-(3-alkoxyimino-5-amino/methylaminopiperidin-1-yl)fluoroquinolone derivatives based on the structures of new fluoroquinolones IMB and DZH. The antibacterial activity of these newly synthesized compounds was also evaluated and compared with gemifloxacin, ciprofloxacin, and levofloxacin. Results revealed that all of the target compounds 10-27 have good potency in inhibiting the growth of Staphylococcus aureus including MSSA (MIC: 0.125-8 μg/mL), Staphylococcus epidermidis including MRSE (MIC: 0.25-16 μg/mL), Streptococcus pneumoniae (MIC: 0.125-4 μg/mL), and Escherichia coli (MIC: 0.25-0.5 μg/mL). In particular, some compounds showed useful activity against several fluoroquinolone-resistant strains, and the most active compound 15 was found to be 16-128, 2-32, and 4-8-fold more potent than the three reference drugs against fluoroquinolone-resistant MSSA, MRSA, and MRSE. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/21232952/Synthesis_and_in_vitro_antibacterial_activity_of_7__3_alkoxyimino_5_amino/methylaminopiperidin_1_yl_fluoroquinolone_derivatives_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(10)01837-8 DB - PRIME DP - Unbound Medicine ER -