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Semisynthesis of CRV431.

Feng-Xia Li¹, Qing-Zhou Zhang¹, Shi-Jun Li²

¹State Key Laboratory of Chemical Oncogenomics and Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

Organic Letters

|April 12, 2021

Summary

CRV431, a non-immune-suppressive cyclophilin inhibitor, shows promise for treating nonalcoholic steatohepatitis (NASH), liver fibrosis, and cancer. A new four-step chemical semisynthesis makes this potential therapeutic more accessible.

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Area of Science:

Medicinal Chemistry
Organic Synthesis
Hepatology

Background:

Nonalcoholic steatohepatitis (NASH) is a progressive liver disease with significant unmet medical needs.
CRV431 is a novel, non-immune-suppressive cyclophilin inhibitor with demonstrated potential in treating NASH, liver fibrosis, and reducing cancer incidence.
Existing synthetic routes may limit the accessibility of CRV431 for further clinical development.

Purpose of the Study:

To develop a concise and efficient chemical semisynthesis of the therapeutic candidate CRV431.
To establish a scalable synthetic route from a readily available starting material.

Main Methods:

A four-step semisynthesis of CRV431 was designed starting from commercially available cyclosporine.
Key transformations included flow-chemistry-based methylenation, intermolecular ring-closing metathesis, and Rh-catalyzed diastereoselective hydrogenation.

Main Results:

A concise four-step semisynthesis of CRV431 was successfully achieved.
The synthetic route utilizes key modern organic chemistry techniques, including flow chemistry and metal catalysis.
This streamlined synthesis enhances the accessibility of CRV431 for further research and clinical application.

Conclusions:

The developed semisynthesis provides an efficient and accessible route to CRV431.
This advancement supports the further clinical investigation of CRV431 as a potential treatment for NASH, liver fibrosis, and associated cancers.