| pubmed-article:14556791 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C0140057 | lld:lifeskim |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C0023688 | lld:lifeskim |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C1510827 | lld:lifeskim |
| pubmed-article:14556791 | lifeskim:mentions | umls-concept:C1611588 | lld:lifeskim |
| pubmed-article:14556791 | pubmed:issue | 22 | lld:pubmed |
| pubmed-article:14556791 | pubmed:dateCreated | 2003-10-14 | lld:pubmed |
| pubmed-article:14556791 | pubmed:abstractText | We have explored the synthesis of compounds that have good affinity for both mu- and delta-opioid receptors from the (alphaR,2S,5S) class of diaryldimethylpiperazines. These non-selective compounds were related to opioids that have been found to interact selectively with mu- or delta-opioid receptors as agonists or antagonists. In our initial survey, we found two compounds, (+)-4-[(alphaR)-alpha-(4-allyl-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide (14) and its N-H relative, (-)-4-[(alphaR)-alpha-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide (15), that interacted with delta-receptors with good affinity, and, as we hoped, with much higher affinity at mu-receptors than SNC80. The relative configuration of the benzylic position in (+)-4-[(alphaR)-alpha-(4-allyl-(2S,5S)-dimethyl-1-piperazinyl)-(3-methoxyphenyl)methyl]-benzyl alcohol (10) was determined by X-ray crystallographic analysis of a crystal that was an unresolved twin. The absolute stereochemistry of that benzylic stereogenic center was unequivocally derived by the X-ray crystallographic analysis from the two other centers of asymmetry in the molecule that were known. Those were established from the synthesis via a dipeptide cyclo-L-Ala-L-Ala in which the absolute stereochemistry was established. | lld:pubmed |
| pubmed-article:14556791 | pubmed:language | eng | lld:pubmed |
| pubmed-article:14556791 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:14556791 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:14556791 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:14556791 | pubmed:month | Nov | lld:pubmed |
| pubmed-article:14556791 | pubmed:issn | 0968-0896 | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:JacobsonArthu... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:RiceKenner... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:DerschChristi... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:RothmanRichar... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:UllrichThomas... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:GeorgeCliffor... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:Flippen-Ander... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:JanetkaJames... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:FurnessM... | lld:pubmed |
| pubmed-article:14556791 | pubmed:author | pubmed-author:KimIn JongIJ | lld:pubmed |
| pubmed-article:14556791 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:14556791 | pubmed:day | 3 | lld:pubmed |
| pubmed-article:14556791 | pubmed:volume | 11 | lld:pubmed |
| pubmed-article:14556791 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:14556791 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:14556791 | pubmed:pagination | 4761-8 | lld:pubmed |
| pubmed-article:14556791 | pubmed:dateRevised | 2006-11-15 | lld:pubmed |
| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
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| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
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| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
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| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
| pubmed-article:14556791 | pubmed:meshHeading | pubmed-meshheading:14556791... | lld:pubmed |
| pubmed-article:14556791 | pubmed:year | 2003 | lld:pubmed |
| pubmed-article:14556791 | pubmed:articleTitle | Diaryldimethylpiperazine ligands with mu- and delta-opioid receptor affinity: Synthesis of (+)-4-[(alphaR)-alpha-(4-allyl-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide and (-)-4-[(alphaR)-alpha-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide. | lld:pubmed |
| pubmed-article:14556791 | pubmed:affiliation | Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA. | lld:pubmed |
| pubmed-article:14556791 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:14556791 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
