SYNTHESIS OF 3′-UREIDOADENOSINE ANALOGUES AND THEIR BINDING AFFINITY TO THE A₃ ADENOSINE RECEPTOR

Moon Woo Chun Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Korea

Hyouk Woo Lee Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Korea

Ae Yil Kim Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea

Myong Jung Kim Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Korea

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

Zhan-Guo Gao Laboratory of Bioorganic Chemistry, Molecular Recognition Section, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland, USA

Kenneth A. Jacobson Laboratory of Bioorganic Chemistry, Molecular Recognition Section, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland, USA

Lak Shin Jeong Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea

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Abstract

Novel 3′-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding at the A₃ adenosine receptor than the corresponding 3′-aminoadenosine derivatives. However, all synthesized 3′-ureidoadenosine analogues have lost their binding affinities to the all subtypes of adenosine receptors, indicating that bulky 3′-urea moiety led to conformational distortion.

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SYNTHESIS OF 3′-UREIDOADENOSINE ANALOGUES AND THEIR BINDING AFFINITY TO THE A₃ ADENOSINE RECEPTOR

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SYNTHESIS OF 3′-UREIDOADENOSINE ANALOGUES AND THEIR BINDING AFFINITY TO THE A3 ADENOSINE RECEPTOR

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SYNTHESIS OF 3′-UREIDOADENOSINE ANALOGUES AND THEIR BINDING AFFINITY TO THE A₃ ADENOSINE RECEPTOR