Regio- and stereoselective synthesis of truncated 3′-aminocarbanucleosides and their binding affinity at the A3 adenosine receptor

Mun Ju Choi; Girish Chandra; Hyuk Woo Lee; Xiyan Hou; Won Jun Choi; Khai Phan; Kenneth A. Jacobson; Lak Shin Jeong

doi:10.1039/C1OB05853C

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Regio- and stereoselective synthesis of truncated 3′-aminocarbanucleosides and their binding affinity at the A₃adenosinereceptor

Mun Ju Choi,^a Girish Chandra,^a Hyuk Woo Lee,^a Xiyan Hou,^a Won Jun Choi,^ab Khai Phan,^c Kenneth A. Jacobson^c and Lak Shin Jeong*^a

Author affiliations

* Corresponding authors

^a Laboratory of Medicinal Chemistry, College of Pharmacy and Department of Bioinspired Science, Ewha Womans University, Seoul, Korea
E-mail: lakjeong@ewha.ac.kr
Fax: +82-2-3277-2851
Tel: +82-2-3277-3466

^b College of Pharmacy, Dongguk University, Kyungki-do, Korea

^c Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland, USA

Abstract

The stereoselective synthesis of truncated 3′-aminocarbanucleosides 4a–dvia a stereo- and regioselective conversion of a diol 9 to bromoacetate 11a and their binding affinity towards the human A₃ adenosine receptor are described.

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Article information

DOI: https://doi.org/10.1039/C1OB05853C
Article type: Paper
Submitted: 30 May 2011
Accepted: 30 Jun 2011
First published: 01 Jul 2011

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Org. Biomol. Chem., 2011,9, 6955-6962

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Regio- and stereoselective synthesis of truncated 3′-aminocarbanucleosides and their binding affinity at the A₃ adenosine receptor

M. J. Choi, G. Chandra, H. W. Lee, X. Hou, W. J. Choi, K. Phan, K. A. Jacobson and L. S. Jeong, Org. Biomol. Chem., 2011, 9, 6955 DOI: 10.1039/C1OB05853C

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Organic & Biomolecular Chemistry