Transforming theophylline-7-acetic acid into novel beta-lactam derivatives via an unstable ketene containing imidazole moiety and assessing their antibacterial efficacy

IF 2.2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of the Iranian Chemical Society Pub Date : 2024-12-11 DOI:10.1007/s13738-024-03146-z

Parvaneh Agharezaei, Mohammad Reza Islami, Kazem Saidi, Payam Khazaeli

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Abstract

New β-lactams was synthesized by reacting theophylline-7-acetic acid with various Schiff bases in dry CH₂Cl₂ under a nitrogen atmosphere, utilizing the Mukaiyama reagent. The resulting β-lactams featured the theophylline moiety situated at the one position of the four-membered β-lactam ring. This approach represents a formal [2 + 2] cycloaddition of an imine to a novel ketene containing a theophyllinyl group. Remarkably, this chemoselective reaction exclusively yielded the cis-isomer of the β-lactam compound as the sole product. Subsequently, the newly synthesized compounds were evaluated for their antibacterial properties. The findings revealed that compounds 5f and 5g exhibited noteworthy antibacterial effects among the tested β-lactams. Specifically, compound 5f demonstrated activity against Staphylococcus aureus PTCC 2923, while compound 5g displayed activity against both Gram-negative bacteria and Staphylococcus epidermidis PTCC 1435.

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来源期刊

Journal of the Iranian Chemical Society 化学-化学综合

CiteScore

4.40

自引率

8.30%

发文量

230

审稿时长

5.6 months

期刊介绍： JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.