Synthesis of new penicillin derivatives as drug-like molecules for biological screening

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Synthesis of new penicillin derivatives as drug-like molecules for biological screening

Chun-Jing Liu , Dinah Dutta , Lester Mitscher

Citation: Chun-Jing Liu, Dinah Dutta, Lester Mitscher. Synthesis of new penicillin derivatives as drug-like molecules for biological screening[J]. Chinese Chemical Letters, 2015, 26(1): 113-117. doi: 10.1016/j.cclet.2014.09.008 shu

shu

Synthesis of new penicillin derivatives as drug-like molecules for biological screening

通讯作者: Chun-Jing Liu,

摘要: Chemical modification of penicillin β-lactam ring was made. Six thiazolidine amides were produced through N4-C7 β-lactam ring opening of penicillin V methyl ester with various aliphatic, aromatic, and heterocyclic primary amines. Five 8-hydroxypenillic acid derivatives with side chains of methyl, propyl, benzyl, and diethylaminoethyl groups were yielded via β-lactam ring rearrangement from 6-aminopenicillanic acid (6-APA). Parallel synthetic methods were used for the alkylation of 8-hydroxypenillic acid and β-lactam ring opening of penicillin V methyl ester. The biological activities of the compounds were evaluated.

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English

Synthesis of new penicillin derivatives as drug-like molecules for biological screening

1.
a Higuchi Biosciences Center, The University of Kansas, Lawrence KS66045, USA;
2.
b Department of Medicinal Chemistry, The University of Kansas, Lawrence KS66045, USA

Corresponding author: Chun-Jing Liu,

Received Date: 22 May 2014
Available Online: 16 September 2014

Abstract: Chemical modification of penicillin β-lactam ring was made. Six thiazolidine amides were produced through N4-C7 β-lactam ring opening of penicillin V methyl ester with various aliphatic, aromatic, and heterocyclic primary amines. Five 8-hydroxypenillic acid derivatives with side chains of methyl, propyl, benzyl, and diethylaminoethyl groups were yielded via β-lactam ring rearrangement from 6-aminopenicillanic acid (6-APA). Parallel synthetic methods were used for the alkylation of 8-hydroxypenillic acid and β-lactam ring opening of penicillin V methyl ester. The biological activities of the compounds were evaluated.

Key words:

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