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微波辅助短时间清洁合成 1,3-二酮作为杂环合成中的构建块:新型二氢吡啶、4H-吡喃、二氢嘧啶嗪、嘧啶和吡唑衍生物的简便合成及抗菌评价。

Microwave assisted the short time clean synthesis of 1,3-diketones as building blocks in heterocyclic synthesis: a facile synthesis and antimicrobial evaluation of new dihydropyridine, 4H-pyrane, dihydropyridazine, pyrimidine and pyrazole derivatives.

机构信息

Department of Chemistry, Faculty of Science, Arish University, Arish, 45511, Egypt.

出版信息

Mol Divers. 2022 Apr;26(2):741-755. doi: 10.1007/s11030-020-10152-9. Epub 2021 Jan 5.

DOI:10.1007/s11030-020-10152-9
PMID:33398634
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9064864/
Abstract

The compounds bearing naphthalene moiety can be used as medical preparations because of their wide spectrum of biological activity and low toxicity. In this study, a new series of azoles or azines were synthesized from the reaction of the key intermediate 1-(1-hydroxynaphthalen-2-yl)-3-phenylpropane-1,3-dione 3 with a variety of electrophilic and nucleophilic reagents under a variety of mild conditions. The chemical structures of these compounds were confirmed by various spectroscopic methods such as (IR, H-NMR, C-NMR, mass spectra and elemental analyses). The prepared compounds were screened in vitro for their anti-microbial activity against some species of Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeuroginosa). Anti-fungal activities of the compounds were tested against yeast and mycelial fungi,Candida albicans and Aspergillus flavus. The antimicrobial activity of this series was showed either weak or moderate activities.

摘要

含萘环部分的化合物由于具有广泛的生物活性和低毒性,可作为药物制剂。在这项研究中,通过关键中间体 1-(1-羟基-2-萘基)-3-苯基-1,3-丙二酮 3 与各种亲电和亲核试剂在多种温和条件下反应,合成了一系列新的唑类或嗪类化合物。这些化合物的化学结构通过各种光谱方法(如(IR、H-NMR、C-NMR、质谱和元素分析)得到确认。合成的化合物在体外进行了抗微生物活性筛选,以测试它们对一些革兰氏阳性菌(金黄色葡萄球菌和枯草芽孢杆菌)和革兰氏阴性菌(大肠杆菌和铜绿假单胞菌)的抑制作用。化合物的抗真菌活性也对酵母和丝状真菌(白色念珠菌和黄曲霉)进行了测试。该系列化合物的抗菌活性表现出较弱或中等的活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/46f0ed7d7729/11030_2020_10152_Sch9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/3c60d2f47243/11030_2020_10152_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/b339cd118d2b/11030_2020_10152_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/0f94bfb311a1/11030_2020_10152_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/ce7721c12b8c/11030_2020_10152_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/f7ff82b06403/11030_2020_10152_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/49e66c613a58/11030_2020_10152_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/61d2c0ef85b1/11030_2020_10152_Sch7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/41664b8c5890/11030_2020_10152_Sch8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/46f0ed7d7729/11030_2020_10152_Sch9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/3c60d2f47243/11030_2020_10152_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/b339cd118d2b/11030_2020_10152_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/0f94bfb311a1/11030_2020_10152_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/ce7721c12b8c/11030_2020_10152_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/f7ff82b06403/11030_2020_10152_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/49e66c613a58/11030_2020_10152_Sch6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/61d2c0ef85b1/11030_2020_10152_Sch7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/41664b8c5890/11030_2020_10152_Sch8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5d9f/9064864/46f0ed7d7729/11030_2020_10152_Sch9_HTML.jpg

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