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Design and synthesis of 3′-ureidoadenosine-5′-uronamides: Effects of the 3′-ureido group on binding to the A 3 adenosine receptor

Title
Design and synthesis of 3′-ureidoadenosine-5′-uronamides: Effects of the 3′-ureido group on binding to the A 3 adenosine receptor
Authors
Jeong L.S.Kim M.J.Kim H.O.Gao Z.-G.Kim S.-K.Jacobson K.A.Chun M.W.
Ewha Authors
정낙신
Issue Date
2004
Journal Title
Bioorganic and Medicinal Chemistry Letters
ISSN
0960-894XJCR Link
Citation
Bioorganic and Medicinal Chemistry Letters vol. 14, no. 19, pp. 4851 - 4854
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
Novel 3′-ureidoadenosine analogues, 3 and 4 were synthesized from 1,2:5,6-di-O-isopropylidene-d-glucose in order to cause stronger hydrogen bonding than the corresponding 3′-aminoadenosine derivatives at the A 3 adenosine receptor. On the basis of high binding affinity at the A 3 adenosine receptor of 3′-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3′-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-d-glucose in order to lead to stronger hydrogen bonding than the corresponding 3′-aminoadenosine derivatives. However, the synthesized 3′-ureidoadenosine analogues were totally devoid of binding affinity, because 3′-urea moiety caused steric and electrostatic repulsions at the binding site of the A 3 adenosine receptor, leading to conformational distortion. © 2004 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.bmcl.2004.07.042
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약학대학 > 약학과 > Journal papers
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