Enantioselective 1,4-addition of kojic acid derivatives to β-nitroolefins catalyzed by a cinchonine derived sugar thiourea

被引：21

作者：

Reddy, B. V. Subba ^{[1
]}

Reddy, S. Madhusudana ^{[1
]}

Swain, Manisha ^{[1
]}

Dudem, Srikanth ^{[2
]}

Kalivendi, Shasi V. ^{[2
]}

Reddy, C. Suresh ^{[3
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500607, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Ctr Chem Biol, Hyderabad 500607, Andhra Pradesh, India

[3] Sri Venkateswra Univ, Dept Chem, Tirupati, Andhra Pradesh, India

来源：

RSC ADVANCES | 2014年 / 4卷 / 18期

关键词：

MICHAEL ADDITION; CONJUGATE ADDITION; TUMOR PROMOTERS; CHALCONES; DESIGN; AMIDE;

D O I：

10.1039/c3ra47423b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective Michael addition reaction of kojic acid derivatives to beta-nitroolefins has been accomplished using a cinchonine derived sugar thiourea. The reaction provides the corresponding Michael adducts in excellent yields with a high degree of enantioselectivity (up to 99% ee) in short reaction time with low catalyst loading. The Michael adducts are found to exhibit promising cytotoxicity against various cancer cell lines.

引用

页码：9107 / 9111

页数：5

共 47 条

[1] Effects of mycotoxins, kojic acid and oxalic acid, on biological fitness of Lygus hesperus (Heteroptera: Miridae) [J].

Alverson, J .

JOURNAL OF INVERTEBRATE PATHOLOGY, 2003, 83 (01) :60-62

[2]

Aytemir MD, 2003, TURK J CHEM, V27, P757

[3]

Aytemir MD, 2003, TURK J CHEM, V27, P445

[4]

Aytemir MD, 2010, ARZNEIMITTELFORSCH, V60, P22, DOI 10.1055/s-0031-1296244

[5]

Brtko J., 2004, CENT EUR J PUBL HEAL, V12, P8

[6] Evaluation of health aspects of kojic acid in food [J].

Burdock, FA ;

Soni, MG ;

Carabin, IG .

REGULATORY TOXICOLOGY AND PHARMACOLOGY, 2001, 33 (01) :80-101

[7] Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect [J].

Cao, Xiao-Yu ;

Zheng, Jun-Cheng ;

Li, Yu-Xue ;

Shu, Zhen-Cao ;

Sun, Xiu-Li ;

Wang, Bi-Qin ;

Tang, Yong .

TETRAHEDRON, 2010, 66 (51) :9703-9707

[8] Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency [J].

Chen, Jia-Rong ;

Cao, Yi-Ju ;

Zou, You-Quan ;

Tan, Fen ;

Fu, Liang ;

Zhu, Xiao-Yu ;

Xiao, Wen-Jing .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) :1275-1279

[9] INHIBITORY EFFECT OF KOJIC ACID ON SOME PLANT AND CRUSTACEAN POLYPHENOL OXIDASES [J].

CHEN, JS ;

WEI, CI ;

ROLLE, RS ;

OTWELL, WS ;

BALABAN, MO ;

MARSHALL, MR .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (08) :1396-1401

[10] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

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