DC Field | Value | Language |
---|---|---|
dc.contributor.author | Susan M. Ludeman | ko |
dc.contributor.author | Ellen M. Shulman-Roskes | ko |
dc.contributor.author | Michael P. Gamcsik | ko |
dc.contributor.author | Terence G. Hamill | ko |
dc.contributor.author | Young N. Chang | ko |
dc.contributor.author | Kyo I. Koo | ko |
dc.contributor.author | O. Michael Colvin | ko |
dc.date.accessioned | 2013-02-25T17:21:08Z | - |
dc.date.available | 2013-02-25T17:21:08Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 1993-04 | - |
dc.identifier.citation | JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, v.33, no.4, pp.313 - 326 | - |
dc.identifier.issn | 0362-4803 | - |
dc.identifier.uri | http://hdl.handle.net/10203/63887 | - |
dc.description.abstract | The cyclophosphamide metabolite phosphoramide mustard (PM) was synthesized with isotopic enrichment at each nitrogen and oxygen site. Sequential reaction of N,N-bis(2-chloroethyl)phosphoramidic dichloride [Cl2P(O)N(CH2CH2Cl)2] with benzyl alcohol and ammonia gave N,N-bis(2-chloroethyl)phosphorodiamidic acid phenylmethyl ester [BzO(H2N)P(O)N(CH2CH2Cl)2] . Catalytic hydrogenation of this benzyl ester followed by the addition of cyclohexylamine (CHA) provided PM as the CHA salt. Incorporation of (NH3)-N-15 into this general scheme gave PM with a (NH2)-N-15 moiety. Glycine-N-15 was converted to bis(2-chloro-ethyl)amine-N-15 hydrochloride which, in turn, provided for N,N-bis(2-chloroethyl)phosphoramidic-N-15 dichloride. Use of this compound in the general synthetic pathway yielded PM-CHA with N-15 in the mustard moiety. O-17-Enriched PM was generated through the use of benzyl alcohol-O-17. To obtain the alcohol, labelled benzaldehyde was made by exchange with (OH2)-O-17, and was then reduced with sodium borohydride. | - |
dc.language | English | - |
dc.publisher | Wiley-Blackwell | - |
dc.title | Synthesis of 15N and 17O Labelled Phosphoramide Mustards | - |
dc.type | Article | - |
dc.identifier.wosid | A1993KW68500009 | - |
dc.identifier.scopusid | 2-s2.0-0027418395 | - |
dc.type.rims | ART | - |
dc.citation.volume | 33 | - |
dc.citation.issue | 4 | - |
dc.citation.beginningpage | 313 | - |
dc.citation.endingpage | 326 | - |
dc.citation.publicationname | JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | - |
dc.contributor.localauthor | Young N. Chang | - |
dc.contributor.nonIdAuthor | Susan M. Ludeman | - |
dc.contributor.nonIdAuthor | Ellen M. Shulman-Roskes | - |
dc.contributor.nonIdAuthor | Michael P. Gamcsik | - |
dc.contributor.nonIdAuthor | Terence G. Hamill | - |
dc.contributor.nonIdAuthor | Kyo I. Koo | - |
dc.contributor.nonIdAuthor | O. Michael Colvin | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | N-15-PHOSPHORAMIDE MUSTARD | - |
dc.subject.keywordAuthor | O-17-PHOSPHORAMIDE MUSTARD | - |
dc.subject.keywordAuthor | BIS(2-CHLOROETHYLAMINE-N-15 | - |
dc.subject.keywordAuthor | BENZYL ALCOHOL-O-17 | - |
dc.subject.keywordAuthor | CYCLOPHOSPHAMIDE | - |
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