| pubmed-article:2500527 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0003451 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0439849 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0596402 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0034287 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0040562 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0441655 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0445223 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C1552599 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C1704787 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C1611588 | lld:lifeskim |
| pubmed-article:2500527 | lifeskim:mentions | umls-concept:C0074024 | lld:lifeskim |
| pubmed-article:2500527 | pubmed:issue | 7 | lld:pubmed |
| pubmed-article:2500527 | pubmed:dateCreated | 1989-8-4 | lld:pubmed |
| pubmed-article:2500527 | pubmed:abstractText | A number of 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine derivatives related to the nucleoside antibiotics toyocamycin and sangivamycin were prepared and tested for their biological activity. Treatment of the sodium salt of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (1) with (2-acetoxyethoxy)methyl bromide (2) afforded a mixture of 4-amino-6-bromo-5-cyano-7-[(2-acetoxyethoxy)methyl]pyrrolo[2,3-d] pyrimidine (3) and the corresponding N1 isomer. Debromination of this mixture gave the corresponding 4-amino-5-cyano-7-[(2-acetoxyethoxy)-methyl]pyrrolo[2,3-d]pyrimidi ne (4) and 4-amino-5-cyano-1-[(2-acetoxyethoxy)methyl]pyrrolo[2,3-d]pyrimidin e (5). Deacetylation of 4 and 5 furnished 4-amino-5-cyano-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine (6) and the corresponding N1 isomer (7), respectively. The sites of attachment for the acyclic moiety for 6 and 7 were assigned on the basis of UV spectral studies as well as 13C NMR spectroscopy. Conventional functional group transformation of 6 provided a number of novel 5-substituted derivatives (8-10), including the sangivamycin derivative 8. The methyl formimidate derivative 10 was converted to the thioamide derivative 11 and the carbohydrazide derivative 12. Compounds 6 and 8-12 were tested for cytotoxicity to L1210 murine leukemic cells in vitro. None of these compounds caused significant inhibition of cell growth. Evaluation of compounds 4 and 6-12 for activity against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) revealed that only the thioamide (11) was active. It inhibited HCMV but not HSV-1 at concentrations producing only slight cytotoxicity in human foreskin fibroblasts (HFF cells) and KB cells. | lld:pubmed |
| pubmed-article:2500527 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:language | eng | lld:pubmed |
| pubmed-article:2500527 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:2500527 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:2500527 | pubmed:month | Jul | lld:pubmed |
| pubmed-article:2500527 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:GuptaP KPK | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:DrachJ CJC | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:TownsendL BLB | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:WotringL LLL | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:NassiriM RMR | lld:pubmed |
| pubmed-article:2500527 | pubmed:author | pubmed-author:ColemanL ALA | lld:pubmed |
| pubmed-article:2500527 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:2500527 | pubmed:volume | 32 | lld:pubmed |
| pubmed-article:2500527 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:2500527 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:2500527 | pubmed:pagination | 1420-5 | lld:pubmed |
| pubmed-article:2500527 | pubmed:dateRevised | 2008-11-21 | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
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| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:meshHeading | pubmed-meshheading:2500527-... | lld:pubmed |
| pubmed-article:2500527 | pubmed:year | 1989 | lld:pubmed |
| pubmed-article:2500527 | pubmed:articleTitle | Synthesis, cytotoxicity, and antiviral activity of certain 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine nucleosides related to toyocamycin and sangivamycin. | lld:pubmed |
| pubmed-article:2500527 | pubmed:affiliation | Department of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor 48109-1065. | lld:pubmed |
| pubmed-article:2500527 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:2500527 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
| pubmed-article:2500527 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:2500527 | lld:chembl |
