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咪唑并吡啶的合成：NaIO/TBHP促进的(3 + 2)环加成反应及作为抗癌剂的生物学评价

Synthesis of imidazopyridines NaIO/TBHP-promoted (3 + 2) cycloaddition and biological evaluation as anticancer agents.

作者信息

Luo Huiping, Hu Zhengyu, Shi Jihai, Lou Yongxin, Shi Zhonghua, Jin Xin, Chen Jia, Liu Xing, Huang Qiang

机构信息

School of Pharmacy, Zunyi Medical University Zunyi Guizhou 563006 China

The First Clinical Institute, Zunyi Medical University Zunyi 563006 China.

出版信息

RSC Adv. 2025 May 12;15(20):15497-15504. doi: 10.1039/d5ra01949d.

DOI:10.1039/d5ra01949d
PMID:40365224
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12067191/
Abstract

A novel and simple NaIO/TBHP-promoted (3 + 2) cycloaddition reaction of propargyl alcohols and 2-aminopyridines was discovered for the synthesis of imidazo[1,2-]pyridines. This protocol exhibits a broad substrate scope for both propargyl alcohols and 2-aminopyridines, with high functional group tolerance, leading to the formation of various C3-carbonylated imidazopyridines in moderate yields. More importantly, these synthesized compounds were evaluated for their antiproliferation activity against MOLM-13 and MV4-11 cells, indicating that 3n, 5a and 5d possessed good bioactivity. Molecular docking analysis showed the strong interaction between 5a, 5d and FLT3 kinase, which have practical values in the development of kinase inhibitors.

摘要

发现了一种新颖且简单的由碘酸钠/叔丁基过氧化氢促进的炔丙醇与2-氨基吡啶的(3 + 2)环加成反应，用于咪唑并[1,2 -]吡啶的合成。该方法对炔丙醇和2-氨基吡啶均具有广泛的底物范围，具有高官能团耐受性，能以中等产率形成各种C3-羰基化咪唑并吡啶。更重要的是，对这些合成化合物针对MOLM-13和MV4-11细胞的抗增殖活性进行了评估，表明3n、5a和5d具有良好的生物活性。分子对接分析表明5a、5d与FLT3激酶之间存在强相互作用，这在激酶抑制剂的开发中具有实际价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/d186297f9d3f/d5ra01949d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/5c68aac9f9f5/d5ra01949d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/c81d54653681/d5ra01949d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/ec80a72b0a9e/d5ra01949d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/a11f57bb679c/d5ra01949d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/e57fa994c169/d5ra01949d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/d186297f9d3f/d5ra01949d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/5c68aac9f9f5/d5ra01949d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/c81d54653681/d5ra01949d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/ec80a72b0a9e/d5ra01949d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/a11f57bb679c/d5ra01949d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/e57fa994c169/d5ra01949d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0787/12067191/d186297f9d3f/d5ra01949d-f3.jpg

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本文引用的文献

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