Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer

被引：28
|
作者：
Reddy, D. Kumar [1 ]
Shekhar, V. [1 ]
Prabhakar, P. [1 ]
Babu, B. Chinna [1 ]
Siddhardha, B. [2 ]
Murthy, U. S. N. [2 ]
Venkateswarlu, Y. [1 ]
机构：
[1] Indian Inst Chem Technol, Nat Prod Lab, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Div Biol, Hyderabad 500007, Andhra Pradesh, India
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 10期
关键词：
(R)-rugulactone; (6R)-(4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one; Inhibitor of NF-kappa B activation pathway; Antibacterial activity; Antifungal activity; LACTONE;
D O I：
10.1016/j.ejmech.2010.07.036
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A simple and highly efficient synthetic route has been developed for synthesis of (R)-rugulactone (1a), (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one (1b) and its 4S epimer 1c by employing proline-catalyzed alpha-aminooxylation, Sharpless epoxidation, Mitsunobu reaction as chirality introuducing steps. The antibacterial and antifungal activity of the compounds 1a, 1b and 1c were evaluated 1a and 1b showed better antibacterial activity against Pseudomonas aeroginosa (MIC =12.5 mu g/ml for la, 25 mu g/ml for 1b) Klebsiella pneumonia (MIC =25 mu g/ml for 1a) Compounds (1a, 1b, 1c) exhibited good to moderate antifungal activity. (C) 2010 Elsevier Masson SAS All rights reserved.
引用
收藏
页码：4657 / 4663
页数：7
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