A Practical Transition Metal-Free Synthesis of Highly Substituted Thiophenes Containing a Benzoxazole Moiety and Their Antimicrobial Activity

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-12-19 DOI:10.1134/S1070428024100105
A. Hfaiedh, I. Smari, H. Marzouki, Ch. Youssef, H. Ben Ammar
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Abstract

Two new series of 3-(pyrrol-1-yl)thiophene derivatives 3a3c and 3-amino-4-(1,3-benzoxazol-2-yl)-5-(substituted-amino)thiophene derivatives 5a5f were synthesized in 75–85% and up to 91% yields, respectively, from readily available and simple substrates. Substrates 2a–2c underwent an amino group change into a pyrrole unit on heating in acetic acid. This protocol has been proven effective by a scaled-up reaction and synthetic transformation. The functional group tolerance and substrate scope of this approach were both approved. It was also possible to prepare substituted thiophenes in a single process. The synthesized thiophene derivatives were tested for their antibacterial effects. The results showed that the presence of a ketone group on the thiophene unit was more efficient compared to the ester group. Compounds 2c, 5b, and 5c showed higher antibacterial activity against both Gram-positive and Gram-negative bacteria. Particularly, compound 5b exhibited the highest antibacterial activity with a MIC value of 0.0625 mg/mL against Staphylococcus aureus, Escherichia coli, and Candida albicans and with a MIC value of 0.125 mg/mL for Bacillus subtilis, Salmonella enterica, and Pseudomonas aeruginosa.

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含苯并恶唑高取代噻吩的无过渡金属合成及其抑菌活性
本文利用易获得的和简单的底物合成了两个新的3-(吡咯-1-基)噻吩衍生物3a-3c和3-氨基-4-(1,3-苯并恶唑-2-基)-5-(取代氨基)噻吩衍生物5a-5f,产率分别为75-85%和高达91%。底物2a-2c在乙酸中加热时发生氨基转变为吡咯单元。通过放大反应和合成转化,证明了该方案的有效性。该方法的功能基耐受性和底物范围均得到认可。也有可能在单一工艺中制备取代噻吩。对合成的噻吩衍生物进行了抗菌性能测试。结果表明,与酯基相比,噻吩单元上存在酮基的效率更高。化合物2c、5b和5c对革兰氏阳性菌和革兰氏阴性菌均有较高的抑菌活性。其中,化合物5b对金黄色葡萄球菌、大肠杆菌和白色念珠菌的MIC值为0.0625 mg/mL,对枯草芽孢杆菌、肠炎沙门氏菌和铜绿假单胞菌的MIC值为0.125 mg/mL,抗菌活性最高。
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来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
期刊介绍: Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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