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在通往新型4-苯胺基喹唑啉类潜在抗癌药物的过程中4-氯喹唑啉的高效芳基化反应

Efficient -arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents.

作者信息

Nishimura Rodolfo H V, Dos Santos Thiago, Murie Valter E, Furtado Luciana C, Costa-Lotufo Leticia V, Clososki Giuliano C

机构信息

Núcleo de Pesquisas em Produtos Naturais e Sintéticos, Departamento de Ciências BioMoleculares, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café s/n, Ribeirão Preto-SP 14040-903, Brazil.

Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto-SP, Universidade de São Paulo, Av. dos Bandeirantes 3900, Ribeirão Preto-SP 14090-901, Brazil.

出版信息

Beilstein J Org Chem. 2021 Dec 22;17:2968-2975. doi: 10.3762/bjoc.17.206. eCollection 2021.

DOI:10.3762/bjoc.17.206
PMID:35003373
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8712970/
Abstract

Microwave-mediated -arylation of 4-chloroquinazolines in THF/HO rapidly and efficiently afforded a library of novel 6-halo-2-phenyl-substituted 4-anilinoquinazolines. The methodology was compatible with numerous , , and -substituted -methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties.

摘要

在四氢呋喃/水体系中，微波介导的4-氯喹唑啉的芳基化反应能够快速、高效地构建一系列新型的6-卤代-2-苯基取代的4-苯胺基喹唑啉文库。该方法适用于多种邻位、间位和对位取代的甲基苯胺以及取代苯胺，能以良好的产率得到相应的4-苯胺基喹唑啉。对合成化合物针对肿瘤细胞（HCT-116和T98G）进行的初步筛选显示出有前景的抗增殖特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/cc151ce39961/Beilstein_J_Org_Chem-17-2968-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/f5448f1dd50c/Beilstein_J_Org_Chem-17-2968-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/3ecb5295739d/Beilstein_J_Org_Chem-17-2968-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/12e6c2f9aad0/Beilstein_J_Org_Chem-17-2968-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/d2eb8212c912/Beilstein_J_Org_Chem-17-2968-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/f751553d0860/Beilstein_J_Org_Chem-17-2968-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/cc151ce39961/Beilstein_J_Org_Chem-17-2968-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/f5448f1dd50c/Beilstein_J_Org_Chem-17-2968-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/3ecb5295739d/Beilstein_J_Org_Chem-17-2968-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/12e6c2f9aad0/Beilstein_J_Org_Chem-17-2968-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/d2eb8212c912/Beilstein_J_Org_Chem-17-2968-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/f751553d0860/Beilstein_J_Org_Chem-17-2968-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/946e/8712970/cc151ce39961/Beilstein_J_Org_Chem-17-2968-g007.jpg

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本文引用的文献

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Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents.使用混合锂-镁试剂合成 7-氯喹啉衍生物。
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Selective Metalation and Functionalization of Fluorinated Nitriles Using 2,2,6,6-Tetramethylpiperidyl Bases.使用 2,2,6,6-四甲基哌啶碱对氟化腈进行选择性金属化和功能化。
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Potential of substituted quinazolines to interact with multiple targets in the treatment of cancer.
取代喹唑啉类化合物在癌症治疗中与多个靶点相互作用的潜力。
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Therapeutic progression of quinazolines as targeted chemotherapeutic agents.喹唑啉类作为靶向化疗药物的治疗进展。
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Novel promising 4-anilinoquinazoline-based derivatives as multi-target RTKs inhibitors: Design, molecular docking, synthesis, and antitumor activities in vitro and vivo.新型有前景的 4-苯胺基喹唑啉类衍生物作为多靶点 RTKs 抑制剂的设计、分子对接、合成及体外和体内抗肿瘤活性。
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Design, synthesis and biological evaluation of novel 4-anilinoquinazoline derivatives as hypoxia-selective EGFR and VEGFR-2 dual inhibitors.新型 4-苯胺喹唑啉衍生物的设计、合成及作为低氧选择性 EGFR 和 VEGFR-2 双重抑制剂的生物评价。
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