Synthesis of some chalcones derivatives series and their antituberculosis activity

IF 2 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Pure and Applied Chemistry Pub Date : 2024-01-24 DOI:10.1515/pac-2023-1127

Noviany Noviany, Hasnah Osman, Suriyati Mohamad, Sutopo Hadi, Heri Satria, Buhani Buhani

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引用次数: 0

Abstract

Chalcone is an important biosynthetic precursor, due to the diverse pharmacological activities. The aim of this current study was to synthesize 14 new chalcone derivatives compounds by incorporating p-alkoxyacetophenones with substituted benzaldehydes. Two new series of chalcone derivatives have been synthesized using the alkylation and the base catalysed Claisen-Schmidt condensation. All the synthesized compounds were fully characterized by IR, 1D NMR (1H and 13C NMR) and 2D NMR (COSY, HMQC, HMBC) as well as mass spectrometry analysis. All the synthesized compounds were assayed in vitro for their antituberculosis activities against Mycobacterium tuberculosis strain. Among them, compounds (E)-1-[4-(heptoxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5a), (E)-1-[4-(octyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5b) and (E)-1-[4-(decyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5d) showed good activities with the lowest MIC value of 12.5 μg/mL.

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一些查耳酮衍生物系列的合成及其抗结核活性

查尔酮是一种重要的生物合成前体，具有多种药理活性。本研究的目的是通过将对烷氧基苯乙酮与取代的苯甲醛结合，合成 14 种新的查尔酮衍生物化合物。通过烷基化和碱催化的克莱森-施密特缩合，合成了两个新系列的查尔酮衍生物。通过红外光谱、一维核磁共振（1H 和 13C NMR）、二维核磁共振（COSY、HMQC、HMBC）以及质谱分析，对所有合成化合物进行了全面鉴定。所有合成的化合物都在体外对结核分枝杆菌菌株进行了抗结核活性检测。其中，化合物 (E)-1-[4-(heptoxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5a)、(E)-1-[4-(octyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5b) 和 (E)-1-[4-(decyloxy)phenyl]-3-(2-hydroxy-5-bromophenyl)prop-2-en-1-one (5d) 显示出良好的活性，最低 MIC 值为 12。5 μg/mL。

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来源期刊

Pure and Applied Chemistry 化学-化学综合

CiteScore

4.00

自引率

0.00%

发文量

审稿时长

3-8 weeks

期刊介绍： Pure and Applied Chemistry is the official monthly Journal of IUPAC, with responsibility for publishing works arising from those international scientific events and projects that are sponsored and undertaken by the Union. The policy is to publish highly topical and credible works at the forefront of all aspects of pure and applied chemistry, and the attendant goal is to promote widespread acceptance of the Journal as an authoritative and indispensable holding in academic and institutional libraries.