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Allgemeiner Zugang zu Polyaminen mit Ethan‐1,2‐diamin‐Einheiten: Synthese von nicht natürlich vorkommenden homologen und isomeren N 1 ,4‐Di(4‐cumaroyl)sperminen
Author(s) -
Lochner Martin,
Geneste Hervé,
Hesse Manfred
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19981216)81:12<2270::aid-hlca2270>3.0.co;2-#
Subject(s) - chemistry , stereochemistry , spermine , medicinal chemistry , organic chemistry , enzyme
█tl="American"█The synthesis of the three N , N ′‐di(4‐coumaroyl)tetramines, i.e. , of ( E , E )‐ N ‐{3‐[(2‐aminoethyl)amino]propyl}‐3,3′‐bis(4‐hydroxyphenyl)‐ N , N ′‐(ethane‐1,2‐diyl)bis[prop‐2‐enamide] ( 1a ), ( E , E )‐ N ‐{4‐[(2‐aminoethyl)amino]butyl}‐3,3′‐bis(4‐hydroxyphenyl)‐ N , N ′‐(ethane‐1,2‐diyl)bis[prop‐2‐enamide] ( 1b ), and ( E , E )‐ N ‐{6‐[(2‐aminoethyl)amino]hexyl}‐3,3′‐bis(4‐hydroxyphenyl)‐ N , N ′‐(ethane‐1,2‐diyl)bis[prop‐2‐enamide] ( 1c ), is described. It proceeds through stepwise construction of the symmetric polyamine backbone including protection and deprotection steps of the amino functions. Their behavior on TLC in comparison with that of 1,4‐di(4‐coumaroyl)spermine (=( E , E )‐ N ‐{4‐[(3‐aminopropyl)amino]butyl}‐3,3′‐bis(4‐hydroxyphenyl)‐ N , N ′‐(propane‐1,3‐diyl)bis[prop‐2‐enamide]; 2 ) is discussed.