Synthesis of 2-amino-9 H-chromeno[2,3- d]thiazol-9-ones with anti-inflammatory activity via cascade reactions of 2-amino-3 iodochromones with amines and carbon disulfide

Jiangtao Tan; Yifan He; Yu Lin; Yuanchen Zhong; Shijun He; Jianping Zuo; Chunhao Yang

doi:10.1039/d3ra07209f

Synthesis of 2-amino-9 H-chromeno[2,3- d]thiazol-9-ones with anti-inflammatory activity via cascade reactions of 2-amino-3 iodochromones with amines and carbon disulfide

RSC Adv. 2024 Jan 19;14(5):3158-3162. doi: 10.1039/d3ra07209f. eCollection 2024 Jan 17.

Authors

Jiangtao Tan^{1

2}, Yifan He^{1

2}, Yu Lin¹, Yuanchen Zhong¹, Shijun He^{1

3}, Jianping Zuo^{1

2}, Chunhao Yang^{1

2}

Affiliations

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia, Medica, Chinese Academy of Sciences 555 Zuchongzhi Road Shanghai 201203 China heshijun@shutcm.edu.cn chyang@simm.ac.cn.
² School of Pharmacy, University of Chinese Academy of Sciences No. 19A YuquanRoad Beijing 100049 China.
³ Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine Shanghai 201203 China.

Abstract

A simple and efficient synthetic approach to 2-amino-9H-chromeno[2,3-d]thiazol-9-ones via copper-promoted cascade reactions was developed. The reaction employed easily available 2-amino-3-iodochromones and amines as substrates and the targeting tricyclic compounds could be obtained with moderate to good yields. Even more important, several synthesized compounds exhibited potent anti-inflammatory activities, which suggested that this protocol may provide valuable hits for drug development in the future.