Direct synthesis of the arylboronic acid analogues of phenylglycine via microwave-assisted four-component Ugi reaction

被引：13

作者：

Lian, Ru-Ching ^{[1
]}

Lin, Meng-Hsuan ^{[1
]}

Liao, Pin-Hsuan ^{[1
]}

Fu, Jia-Jie ^{[1
]}

Wu, Meng-Ju ^{[1
]}

Wu, Yang-Chang ^{[2
,3
,4
]}

Chang, Fang-Rong ^{[5
,6
]}

Wu, Chin-Chung ^{[5
]}

Pan, Po-Shen ^{[1
]}

机构：

[1] Tamkang Univ, Dept Chem, New Taipei City 25137, Taiwan

[2] China Med Univ, Sch Pharm, Coll Pharm, Taichung 404, Taiwan

[3] China Med Univ, Chinese Med Res & Dev Ctr, Taichung 404, Taiwan

[4] Kaohsiung Med Univ Hosp, Ctr Canc, Kaohsiung 807, Taiwan

[5] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 807, Taiwan

[6] Kaohsiung Med Univ Hosp, Ctr Canc, Kaohsiung 807, Taiwan

来源：

TETRAHEDRON | 2014年 / 70卷 / 09期

关键词：

Boronic acids; Ugi-4CR; Multicomponent reaction; Microwave-assisted synthesis; Acid/base extraction; PROTEASOME INHIBITOR PS-341; TRANSITION-STATE ANALOG; STRUCTURE-BASED DESIGN; FACTOR-KAPPA-B; 3-NITROBENZENEBORONIC ACID; MULTICOMPONENT REACTIONS; THROMBIN INHIBITORS; BENIGN CATALYST; BORONIC ACIDS; CHYMOTRYPSIN;

D O I：

10.1016/j.tet.2014.01.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A four-component Ugi reaction (Ugi-4CR) utilizing formylphenyl boronic acids under mild condition was developed for the synthesis of arylboronic acid analogs. The reactions were performed in methanol and accelerated by microwave irradiation, which makes this strategy suitable for constructing boronic-containing chemical libraries. Two of the synthesized analogs were found to have cytotoxic activity against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1800 / 1804

页数：5

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