Catalytic Atroposelective Synthesis of Axially Chiral Azomethine Imines and Neuroprotective Activity Evaluation

Author:

Yang Qian‐Qian1,Chen Chen1,Yao Dahong2,Liu Wei3,Liu Bo3,Zhou Jin1,Pan Dabo4,Peng Cheng1,Zhan Gu1,Han Bo1ORCID

Affiliation:

1. State Key Laboratory of Southwestern Chinese Medicine Resources Hospital of Chengdu University of Traditional Chinese Medicine School of Pharmacy Chengdu University of Traditional Chinese Medicine Chengdu 611137 Sichuan China

2. School of Pharmaceutical Sciences Shenzhen Technology University Shenzhen 518060 Guangdong China

3. Department of Biotherapy Cancer Center and State Key Laboratory of Biotherapy West China Hospital Sichuan University Chengdu 610041 Sichuan China

4. State Key Laboratory of Quality Research in Chinese Medicines Macau University of Science and Technology Macau 999078 China

Abstract

AbstractAzomethine imines, as a prominent class of 1,3‐dipolar species, hold great significance and potential in organic and medicinal chemistry. However, the reported synthesis of centrally chiral azomethine imines relies on kinetic resolution, and the construction of axially chiral azomethine imines remains unexplored. Herein, we present the synthesis of axially chiral azomethine imines through copper‐ or chiral phosphoric acid catalyzed ring‐closure reactions of N′‐(2‐alkynylbenzylidene)hydrazides, showcasing high efficiency, mild conditions, broad substrate scope, and excellent enantioselectivity. Furthermore, the biological evaluation revealed that the synthesized axially chiral azomethine imines effectively protect dorsal root ganglia (DRG) neurons by inhibiting apoptosis induced by oxaliplatin, offering a promising therapeutic approach for chemotherapy‐induced peripheral neuropathy (CIPN). Remarkably, the (S)‐ and (R)‐atropisomers displayed distinct neuroprotective activities, underscoring the significance of axial stereochemistry.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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