Molecules 2014, 19(5), 6822-6837; doi:10.3390/molecules19056822
Article

Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate

1,2,†, 2,†, 2, 3, 4, 1 and 1,* email
Received: 14 April 2014; in revised form: 20 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
(This article belongs to the Section Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: A series of amino acid and dipeptide prodrugs of IMB-070593, a fluoroquinolone candidate discovered in our lab, were synthesized and evaluated for their water solubility and then antibacterial activity. Our results reveal that four amino acid prodrugs 4a,b,e,f and two dipeptide prodrugs 4k,l have much greater solubility (>85 mg/mL) than IMB-070593 mesylate (22.5 mg/mL). Compounds 4a and 4k show good in vivo efficacy against MSSA 12-1 (p.o./i.v., 5.32–7.68 mg/kg) and S. pneumoniae12-10 (p.o., 18.39–23.13 mg/kg) which is 1.19–1.50 fold more active than the parent drug.
Keywords: IMB-070593; prodrugs; synthesis; water solubility; antibacterial activity
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MDPI and ACS Style

Zhang, T.; Wu, J.; Chen, S.; Liu, K.; Lin, Y.; Guo, H.; Liu, M. Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate. Molecules 2014, 19, 6822-6837.

AMA Style

Zhang T, Wu J, Chen S, Liu K, Lin Y, Guo H, Liu M. Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate. Molecules. 2014; 19(5):6822-6837.

Chicago/Turabian Style

Zhang, Tingting; Wu, Jinwei; Chen, Shihong; Liu, Kaixiang; Lin, Yabin; Guo, Huiyuan; Liu, Mingliang. 2014. "Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate." Molecules 19, no. 5: 6822-6837.

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