Functional Switch between Pharmacophore and Directing Group and Their Application in Drug Discovery and Development via C-H Activation and Functionalization

doi:10.6023/cjoc201803002

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2465-2490.DOI: 10.6023/cjoc201803002 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

Reviews

药效基团和C—H活化导向基团功能转换在药物研发中的应用

任青云^a,b, 聂飚^a, 张英俊^a,b, 张霁^a,b

a 广东东阳光集团药业研究院东莞 523871;
b 抗感染新药研发国家重点实验室东莞 523871

收稿日期:2018-03-02 修回日期:2018-05-04 发布日期:2018-06-06
通讯作者: 张霁,E-mail:zhangji@hecpharm.com E-mail:zhangji@hecpharm.com
基金资助:
广东省引进创新科研团队计划（No.201301Y0105381261）、抗感染新药研发国家重点实验室（No.2015DQ780357）及国家重大新药创制（No.2018ZX09201002）资助项目.

Functional Switch between Pharmacophore and Directing Group and Their Application in Drug Discovery and Development via C-H Activation and Functionalization

Ren Qingyun^a,b, Nie Biao^a, Zhang Yingjun^a,b, Zhang Ji^a,b

a HEC Pharm Group, HEC R & D Center, Dongguan 523871;
b The State Key Laboratory of Anti-Infective Drug Development, Dongguan 523871

Received:2018-03-02 Revised:2018-05-04 Published:2018-06-06
Contact: 10.6023/cjoc201803002 E-mail:zhangji@hecpharm.com
Supported by:
Project supported by the Introduction of Innovative R&D Team Program of Guangdong Province (No. 201301Y0105381261), the State Key Laboratory of Anti-Infective Drug Development (No. 2015DQ780357) and the National Major Scientific and Technological Special Project for "Significant New Drugs Development" (No. 2018ZX09201002).

The functional switch of a C—H activation directing group to a pharmacophore is introduced and analyzed, and the value of the pharmacophore and the application of C—H activation are exemplified. It is concluded that many pharmacophores, such as N-containing heteroaromatic, nitrile, carboxylic acid, amide and sulfonamide groups, are ideal directing groups for C—H activation enabling the subsequent stages of drug synthesis, and showing that there is a correlation between a directing group and a pharmacophore. The late-stage functionalization will greatly simplify and effectively improve the possibility of discovering new drugs and potentially shortening the overall synthesis. The latest breakthroughs of C—H activation and application in the drug discovery process are reviewed as case studies, providing several industrial examples of using a pharmacophore as directing group for drug synthesis. It is believed that this development will promote a more rapid and green drug synthesis.

Key words: pharmacophore, directing group, C—H activation and functionalization, functional switch between pharmacophore and directing group

Cite this article

Ren Qingyun, Nie Biao, Zhang Yingjun, Zhang Ji. Functional Switch between Pharmacophore and Directing Group and Their Application in Drug Discovery and Development via C-H Activation and Functionalization[J]. Chin. J. Org. Chem., 2018, 38(10): 2465-2490.

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药效基团和C—H活化导向基团功能转换在药物研发中的应用

Functional Switch between Pharmacophore and Directing Group and Their Application in Drug Discovery and Development via C-H Activation and Functionalization

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