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

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

doi:10.1021/acsomega.0c00768

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

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

Authors

Martina Durcik¹, Žan Toplak¹, Nace Zidar¹, Janez Ilaš¹, Anamarija Zega¹, Danijel Kikelj¹, Lucija Peterlin Mašič¹, Tihomir Tomašič¹

Affiliation

¹ University of Ljubljana, Faculty of Pharmacy, Aškerčeva c. 7, SI-1000 Ljubljana, Slovenia.

Abstract

Benzo[d]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[d]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.