Issue 46, 2012
From the journal:

Organic & Biomolecular Chemistry

Diastereoselective ruthenium porphyrin-catalyzed tandem nitrone formation/1,3-dipolar cycloaddition for isoxazolidines. Synthesis, in silico docking study and in vitro biological activities†

Annapureddy Rajasekar Reddy,a   Zhen Guo,a   Fung-Ming Siu,a   Chun-Nam Lok,a   Fuli Liu,a   Kai-Chung Yeung,a   Cong-Ying Zhou*a  and  Chi-Ming Che*a  

* Corresponding authors

a Department of Chemistry, State Key Laboratory of Synthetic Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China
E-mail: cmche@hku.hk, cyzhou@hku.hk
Fax: +(852) 2857-1586
Tel: +(852) 2859-2154

Abstract

Ruthenium porphyrin catalyzes tandem nitrone formation/1,3-dipolar cycloaddition of diazo compounds, nitrosoarenes and alkenes to form isoxazolidines in good to high yields and with excellent regio-, chemo- and diastereo-selectivities. A broad substrate scope of alkenes is applicable to this protocol and various functional groups are compatible with the reaction conditions. In silico analysis and in vitro biological experiments revealed that some of the new isoxazolidines synthesized in this work could act as leukotriene A4 hydrolase inhibitors.

Graphical abstract: Diastereoselective ruthenium porphyrin-catalyzed tandem nitrone formation/1,3-dipolar cycloaddition for isoxazolidines. Synthesis, in silico docking study and in vitro biological activities

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Article information

DOI
https://doi.org/10.1039/C2OB26518D
Article type
Paper
Submitted
25 Jun 2012
Accepted
05 Aug 2012
First published
15 Aug 2012

Org. Biomol. Chem., 2012,10, 9165-9174

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Diastereoselective ruthenium porphyrin-catalyzed tandem nitrone formation/1,3-dipolar cycloaddition for isoxazolidines. Synthesis, in silico docking study and in vitro biological activities

A. Rajasekar Reddy, Z. Guo, F. Siu, C. Lok, F. Liu, K. Yeung, C. Zhou and C. Che, Org. Biomol. Chem., 2012, 10, 9165 DOI: 10.1039/C2OB26518D

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