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作为抗癌和抗菌剂的1,2,3-三唑连接百里酚-1,3,4-恶二唑衍生物的合成与生物学评价

Synthesis and Biological Evaluation of 1,2,3-Triazole Tethered Thymol-1,3,4-Oxadiazole Derivatives as Anticancer and Antimicrobial Agents.

作者信息

Almalki Abdulraheem S A, Nazreen Syed, Malebari Azizah M, Ali Nada M, Elhenawy Ahmed A, Alghamdi Abdullah A A, Ahmad Abrar, Alfaifi Sulaiman Y M, Alsharif Meshari A, Alam Mohammad Mahboob

机构信息

Department of Chemistry, Faculty of Science, Taif University, Taif 21974, Saudi Arabia.

Department of Chemistry, Faculty of Science, Albaha University, Albaha 65731, Saudi Arabia.

出版信息

Pharmaceuticals (Basel). 2021 Aug 28;14(9):866. doi: 10.3390/ph14090866.

DOI:10.3390/ph14090866
PMID:34577567
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8468421/
Abstract

A library of 1,2,3-triazole-incorporated thymol-1,3,4-oxadiazole derivatives (-) hasbeen synthesized and tested for anticancer and antimicrobial activities. Compounds , , , , and exhibited significant antiproliferative activity. Among these active derivatives, compound 2-(4-((5-((2-isopropyl-5-methylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1-1,2,3-triazol-1-yl)phenol () was the best compound against all three tested cell lines, MCF-7 (IC 1.1 μM), HCT-116 (IC 2.6 μM), and HepG2 (IC 1.4 μM). Compound was found to be better than the standard drugs, doxorubicin and 5-fluorouracil. These compounds showed anticancer activity through thymidylate synthase inhibition as they displayed significant TS inhibitory activity with IC in the range 1.95-4.24 μM, whereas the standard drug, Pemetrexed, showed IC 7.26 μM. The antimicrobial results showed that some of the compounds (, , , , and ) exhibited good inhibition on () and (). The molecular docking and simulation studies supported the anticancer and antimicrobial data. It can be concluded that the synthesized 1,2,3-triazole tethered thymol-1,3,4-oxadiazole conjugates have both antiproliferative and antimicrobial potential.

摘要

已合成了一个包含1,2,3 - 三唑的百里酚 - 1,3,4 - 恶二唑衍生物库（-），并对其进行了抗癌和抗菌活性测试。化合物 、 、 、 和 表现出显著的抗增殖活性。在这些活性衍生物中，化合物2 - （4 - （（5 - （（2 - 异丙基 - 5 - 甲基苯氧基）甲基）-1,3,4 - 恶二唑 - 2 - 基硫代）甲基）-1H - 1,2,3 - 三唑 - 1 - 基）苯酚（）是针对所有三种测试细胞系MCF - 7（IC₅₀ 1.1 μM）、HCT - 116（IC₅₀ 2.6 μM）和HepG2（IC₅₀ 1.4 μM）的最佳化合物。发现化合物 优于标准药物阿霉素和5 - 氟尿嘧啶。这些化合物通过抑制胸苷酸合成酶表现出抗癌活性，因为它们显示出显著的TS抑制活性，IC₅₀在1.95 - 4.24 μM范围内，而标准药物培美曲塞的IC₅₀为7.26 μM。抗菌结果表明，一些化合物（ 、 、 、 和 ）对金黄色葡萄球菌（）和大肠杆菌（）表现出良好的抑制作用。分子对接和模拟研究支持了抗癌和抗菌数据。可以得出结论，合成的1,2,3 - 三唑连接的百里酚 - 1,3,4 - 恶二唑共轭物具有抗增殖和抗菌潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/4005b8899c4b/pharmaceuticals-14-00866-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/d11589c4ccd9/pharmaceuticals-14-00866-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/0e74de256813/pharmaceuticals-14-00866-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/62fe65467935/pharmaceuticals-14-00866-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/174d8abc54c2/pharmaceuticals-14-00866-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/5e75b653a865/pharmaceuticals-14-00866-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/4005b8899c4b/pharmaceuticals-14-00866-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/d11589c4ccd9/pharmaceuticals-14-00866-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/0e74de256813/pharmaceuticals-14-00866-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/62fe65467935/pharmaceuticals-14-00866-g002a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/174d8abc54c2/pharmaceuticals-14-00866-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/5e75b653a865/pharmaceuticals-14-00866-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ff9/8468421/4005b8899c4b/pharmaceuticals-14-00866-g005.jpg

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