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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
- SCOPUS Author ID
- 정낙신
- Issue Date
- 2004
- Journal Title
- Bioorganic and Medicinal Chemistry Letters
- ISSN
- 0960-894X
- Citation
- Bioorganic and Medicinal Chemistry Letters vol. 14, no. 19, pp. 4851 - 4854
- Indexed
- SCI; SCIE; 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
- Appears in Collections:
- 약학대학 > 약학과 > Journal papers
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