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高效合成羟基取代的2-氨基苯并噻唑-6-羧酸衍生物作为药物发现中的新型结构单元

Efficient Synthesis of Hydroxy-Substituted 2-Aminobenzo[]thiazole-6-carboxylic Acid Derivatives as New Building Blocks in Drug Discovery.

作者信息

Durcik Martina, Toplak Žan, Zidar Nace, Ilaš Janez, Zega Anamarija, Kikelj Danijel, Mašič Lucija Peterlin, Tomašič Tihomir

机构信息

University of Ljubljana, Faculty of Pharmacy, Aškerčeva c. 7, SI-1000 Ljubljana, Slovenia.

出版信息

ACS Omega. 2020 Mar 31;5(14):8305-8311. doi: 10.1021/acsomega.0c00768. eCollection 2020 Apr 14.

DOI:10.1021/acsomega.0c00768
PMID:32309742
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7161044/
Abstract

Benzo[]thiazole is widely used in synthetic and medicinal chemistry, and it is a component of many compounds and drugs that have several different bioactivities. Herein, we describe an elegant pathway for synthesis of methyl 4- and 5-hydroxy-2-amino-benzo[]thiazole-6-carboxylates as building blocks that can be substituted at four different positions on the bicycle and thus offer the possibility to thoroughly explore the chemical space around the molecule studied as a ligand for the chosen target. A series of 12 new compounds was prepared using the described methods and Williamson ether synthesis.

摘要

苯并噻唑广泛应用于合成化学和药物化学领域，它是许多具有多种不同生物活性的化合物和药物的组成部分。在此，我们描述了一种简洁的合成途径，用于制备4-和5-羟基-2-氨基苯并噻唑-6-羧酸甲酯，作为可以在双环上四个不同位置进行取代的结构单元，从而为深入探索所研究分子作为所选靶点配体周围的化学空间提供了可能性。使用所述方法和威廉姆森醚合成法制备了一系列12种新化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/8cfea214ac97/ao0c00768_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/c2778cb41a5c/ao0c00768_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/3cb52faf4c39/ao0c00768_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/7a0b9d297c46/ao0c00768_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/ba7fc8a06bd3/ao0c00768_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/667ab3286f28/ao0c00768_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/5b8270463dcf/ao0c00768_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/8cfea214ac97/ao0c00768_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/c2778cb41a5c/ao0c00768_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/3cb52faf4c39/ao0c00768_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/7a0b9d297c46/ao0c00768_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/ba7fc8a06bd3/ao0c00768_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/667ab3286f28/ao0c00768_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/5b8270463dcf/ao0c00768_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55ba/7161044/8cfea214ac97/ao0c00768_0007.jpg

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