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基于萘普生的 1,3,4-恶二唑衍生物作为表皮生长因子受体抑制剂：设计、合成、抗癌及计算研究

Naproxen Based 1,3,4-Oxadiazole Derivatives as EGFR Inhibitors: Design, Synthesis, Anticancer, and Computational Studies.

作者信息

Alam Mohammad Mahboob, Nazreen Syed, Almalki Abdulraheem S A, Elhenawy Ahmed A, Alsenani Nawaf I, Elbehairi Serag Eldin I, Malebari Azizah M, Alfaifi Mohammad Y, Alsharif Meshari A, Alfaifi Sulaiman Y M

机构信息

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

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

出版信息

Pharmaceuticals (Basel). 2021 Aug 28;14(9):870. doi: 10.3390/ph14090870.

DOI:10.3390/ph14090870
PMID:34577570
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8469912/
Abstract

A library of novel naproxen based 1,3,4-oxadiazole derivatives (- and -) has been synthesized and screened for cytotoxicity as EGFR inhibitors. Among the synthesized hybrids, compound2-(4-((5-(()-1-(2-methoxynaphthalen-6-yl)ethyl)-1,3,4-oxadiazol-2-ylthio)methyl)-1-1,2,3-triazol-1-yl)phenol() was the most potent compound against MCF-7 and HepG2cancer cells with IC of 2.13 and 1.63 µg/mL, respectively, and was equipotent to doxorubicin (IC 1.62 µg/mL) towards HepG2. Furthermore, compound inhibited EGFR kinase with IC 0.41 μM compared to standard drug Erlotinib (IC 0.30 μM). The active compound induces a high percentage of necrosis towards MCF-7, HePG2 and HCT 116 cells. The docking studies, DFT and MEP also supported the biological data. These results demonstrated that these synthesized naproxen hybrids have EGFR inhibition effects and can be used as leads for cancer therapy.

摘要

已合成了一系列基于萘普生的新型1,3,4-恶二唑衍生物（左旋和右旋），并作为表皮生长因子受体（EGFR）抑制剂进行了细胞毒性筛选。在合成的杂化物中，化合物2-（4-（（5-（（-）-1-（2-甲氧基萘-6-基）乙基）-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MCF-7和HepG2癌细胞最有效的化合物，其IC50分别为2.13和1.63μg/mL，并且对HepG2细胞的活性与阿霉素（IC50 1.62μg/mL）相当。此外，与标准药物厄洛替尼（IC50 0.30μM）相比，化合物对EGFR激酶的抑制IC50为0.41μM。该活性化合物对MCF-7、HePG2和HCT 116细胞诱导产生高比例的坏死。对接研究、密度泛函理论（DFT）和分子静电势（MEP）也支持了这些生物学数据。这些结果表明，这些合成的萘普生杂化物具有EGFR抑制作用，可作为癌症治疗的先导物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/ac6b78d5a400/pharmaceuticals-14-00870-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/6b339bfe5743/pharmaceuticals-14-00870-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/bae38d71917a/pharmaceuticals-14-00870-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/baa7b3ff89fe/pharmaceuticals-14-00870-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/0ef5ae135c70/pharmaceuticals-14-00870-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/a00bb2a1ee77/pharmaceuticals-14-00870-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/0299a6253319/pharmaceuticals-14-00870-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/5d96913fe3fd/pharmaceuticals-14-00870-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/8417c672aff9/pharmaceuticals-14-00870-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/bd7209ffa726/pharmaceuticals-14-00870-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/ac6b78d5a400/pharmaceuticals-14-00870-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/6b339bfe5743/pharmaceuticals-14-00870-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/bae38d71917a/pharmaceuticals-14-00870-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/baa7b3ff89fe/pharmaceuticals-14-00870-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/0ef5ae135c70/pharmaceuticals-14-00870-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/a00bb2a1ee77/pharmaceuticals-14-00870-g003a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/0299a6253319/pharmaceuticals-14-00870-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/5d96913fe3fd/pharmaceuticals-14-00870-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/8417c672aff9/pharmaceuticals-14-00870-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/bd7209ffa726/pharmaceuticals-14-00870-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0947/8469912/ac6b78d5a400/pharmaceuticals-14-00870-g008.jpg

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