DNA-Compatible ortho-Phthalaldehyde (OPA)-Mediated 2-Substituted Isoindole Core Formation and Applications

被引：26

作者：

Nie, Qigui ^{[1
]}

Fang, Xianfu ^{[1
]}

Liu, Changyang ^{[1
]}

Zhang, Gong ^{[1
,2
]}

Fan, Xiaohong ^{[1
,3
]}

Li, Yangfeng ^{[1
,2
]}

Li, Yizhou ^{[1
,2
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Innovat Drug Res Ctr, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

[2] Chongqing Univ, Chem Biol Res Ctr, Sch Pharmaceut Sci, Chongqing 401331, Peoples R China

[3] Chongqing Univ, Three Gorges Hosp, Chongqing Three Gorges Cent Hosp, Pharmaceut Dept, Chongqing 404100, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 05期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

LIBRARIES; CHEMISTRY; BIOCONJUGATION; DESIGN;

D O I：

10.1021/acs.joc.1c02496

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The incorporation of the isoindole core into the DNA-encoded chemical library is highly desirable for the great potential pharmacological characters exampled by molecules like lenalidomide. Herein, we reported a DNA-compatible protocol for the OPA-mediated transformation of amines into drug-like moieties represented by isoindolinone and thio-2-isoindole, respectively. The high conversion and wide substrate-scope property of our protocol render its feasibility in the manipulation of terminal amines on oligonucleotide conjugates, including "cap-and-catch" purification, sequential synthesis during DEL construction, and on-DNA macrocyclization.

引用

页码：2551 / 2558

页数：8

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