| pubmed-article:10814087 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0028621 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0441655 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0376211 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0243071 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C1516050 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0205460 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C1176299 | lld:lifeskim |
| pubmed-article:10814087 | lifeskim:mentions | umls-concept:C0045183 | lld:lifeskim |
| pubmed-article:10814087 | pubmed:issue | 5 | lld:pubmed |
| pubmed-article:10814087 | pubmed:dateCreated | 2000-10-27 | lld:pubmed |
| pubmed-article:10814087 | pubmed:abstractText | Synthesis of spirocyclic analogues of 2'-deoxyadenosine and 2'-deoxyguanosine (12a-15a and 12b-15b) is described. Rhodium-catalyzed reaction of ethyl diazoacetate with methylenecyclopropane 19, obtained from 2-bromo-2-bromomethylcyclopropane 17 via debromination (16), reduction (18), and acetylation (19), gave a mixture of all four isomeric spiropentanes 20a-20d. Hydrolysis afforded hydroxy carboxylic acids 21a-21d. Acetylation of separated proximal + medial-syn isomers 21a + 21b and medial anti + distal isomers 21c + 21d furnished acetates 22a + 22b and 22c + 22d. Curtius rearrangement effected by diphenylphosphoryl azide in tert-butyl alcohol performed separately with mixtures 22a + 22b and 22c + 22d led to BOC-amino spiropentanes 23a + 23b and 23c + 23d. After deacetylation all isomers 24a-24d were separated and deprotected to give aminospiropentane hydrochlorides 25a-25d. Free bases were of limited stability. The heterocyclic moieties were introduced into individual isomers 25a-25d via 6-chloropurine derivatives 26a-26d or 30a-30d. Ammonolysis of 26a-26d furnished the adenine isomeric series 12a-15a, whereas guanine derivatives 12b-15b were obtained by hydrolysis of 30a-30d with formic acid. The isomeric assignments followed from IR spectra of BOC-aminospiropentanes 24a-24d and NMR spectra of 12a-15a including NOE and (H,H) COSY. The proximal and medial-syn isomers 12a and 12b were modest inhibitors of human cytomegalovirus (HCMV) and Epstein-Barr virus (EBV) in culture, whereas the medial-anti isomer 12c was a substrate for adenosine deaminase. The distal isomer 15b was an anti-EBV agent. The medial-syn phosphoralaninate 34 was an effective inhibitor of HCMV replication in vitro. It was also active against herpes simplex virus type 1 (HSV-1), varicella zoster virus (VZV), human immunodeficiency virus (HIV-1), hepatitis B virus (HBV), and EBV with a varying degree of cytotoxicity. | lld:pubmed |
| pubmed-article:10814087 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:language | eng | lld:pubmed |
| pubmed-article:10814087 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:10814087 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:10814087 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:10814087 | pubmed:month | Mar | lld:pubmed |
| pubmed-article:10814087 | pubmed:issn | 0022-3263 | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:DrachJ CJC | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:KernE RER | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:HiebW FWF | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:ChengY CYC | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:ZemlickaJJ | lld:pubmed |
| pubmed-article:10814087 | pubmed:author | pubmed-author:KsebatiM BMB | lld:pubmed |
| pubmed-article:10814087 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:10814087 | pubmed:day | 10 | lld:pubmed |
| pubmed-article:10814087 | pubmed:volume | 65 | lld:pubmed |
| pubmed-article:10814087 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:10814087 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:10814087 | pubmed:pagination | 1280-90 | lld:pubmed |
| pubmed-article:10814087 | pubmed:dateRevised | 2007-11-14 | lld:pubmed |
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| pubmed-article:10814087 | pubmed:meshHeading | pubmed-meshheading:10814087... | lld:pubmed |
| pubmed-article:10814087 | pubmed:meshHeading | pubmed-meshheading:10814087... | lld:pubmed |
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| pubmed-article:10814087 | pubmed:meshHeading | pubmed-meshheading:10814087... | lld:pubmed |
| pubmed-article:10814087 | pubmed:year | 2000 | lld:pubmed |
| pubmed-article:10814087 | pubmed:articleTitle | Spiropentane mimics of nucleosides: analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity. | lld:pubmed |
| pubmed-article:10814087 | pubmed:affiliation | Department of Chemistry, Experimental and Clinical Chemotherapy Program, Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, 110 East Warren Avenue, Detroit, Michigan 48201-1379, USA. | lld:pubmed |
| pubmed-article:10814087 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:10814087 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
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| http://linkedlifedata.com/r... | pubmed:referesTo | pubmed-article:10814087 | lld:pubmed |
