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作为抗癌剂的大环手性特罗格碱苯并吩嗪候选物的合成与表征

Synthesis and Characterization of Macrocyclic Chiral Tröger's Base Phenhomazine Candidates as Anticancer Agent.

作者信息

Ibrahim Alhussein A, Ali Korany A, Hafez Naglaa A Abdel, Elsayed Mohamed A, Mohamed Khalid M H, Hosni Hanaa M, Amr Abd El-Galil E, Elsayed Elsayed A

机构信息

Applied Organic Chemistry Department, National Research Centre, Giza, Egypt.

Pharmacognosy Department, National Research Centre, Giza, Egypt.

出版信息

Front Chem. 2021 Jan 28;8:633065. doi: 10.3389/fchem.2020.633065. eCollection 2020.

DOI:10.3389/fchem.2020.633065
PMID:33748073
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7976657/
Abstract

1,4,7,10-Tetraoxa10trögerophane was synthesized from its corresponding precursors. Heating of with p-nitrophenoxide afforded bis(p-nitrophenyl)ether , which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether . Treatment of with paraformaldehyde and triflouroacetic anhydride gave trögerophane . Reaction of with trifluroacetic anhydride afforded phenhomazine derivative , which was treated with potassium carbonate to afford tetrahydrophenhomazine . Finally, reaction of with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds and , respectively. The synthesized trögerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa10trögerophane had a promising selectivity towards colon cancer cell line with an IC of 92.7 µg/ml.

摘要

1,4,7,10-四氧杂10曲格列酮烷由其相应的前体合成。将其与对硝基苯氧基加热得到双(对硝基苯基)醚，双(对硝基苯基)醚再用肼水处理得到双(对氨基苯基)醚。用多聚甲醛和三氟乙酸酐处理双(对氨基苯基)醚得到曲格列酮烷。双(对氨基苯基)醚与三氟乙酸酐反应得到吩恶嗪衍生物，吩恶嗪衍生物用碳酸钾处理得到四氢吩恶嗪。最后，在三乙胺存在下，双(对氨基苯基)醚与苯甲酰氯、溴乙酸或溴乙酸乙酯回流反应，分别得到相应的大环化合物。对合成的曲格列酮烷、前体及其新合成的吩恶嗪衍生物进行了抗癌活性筛选。结果表明，1,4,7,10-四氧杂10曲格列酮烷对结肠癌细胞系具有良好的选择性，IC50为92.7 µg/ml。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/2d2bfb3d3a74/fchem-08-633065-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/ed02e33c40d0/fchem-08-633065-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/f7e9826f6fa9/fchem-08-633065-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/5acf3e8f327c/fchem-08-633065-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/2d2bfb3d3a74/fchem-08-633065-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/ed02e33c40d0/fchem-08-633065-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/f7e9826f6fa9/fchem-08-633065-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/5acf3e8f327c/fchem-08-633065-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74a5/7976657/2d2bfb3d3a74/fchem-08-633065-g002.jpg

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