Allgemeiner Zugang zu Polyaminen mit Ethan-1,2-diamin-Einheiten: Synthese von nicht natürlich vorkommenden homologen und isomerenN1,4-Di(4-cumaroyl)sperminen

Lochner, Martin; Geneste, Hervé; Hesse, Manfred (1998). Allgemeiner Zugang zu Polyaminen mit Ethan-1,2-diamin-Einheiten: Synthese von nicht natürlich vorkommenden homologen und isomerenN1,4-Di(4-cumaroyl)sperminen. Helvetica chimica acta, 81(12), pp. 2270-2281. Verlag Helvetica Chimica Acta 10.1002/(SICI)1522-2675(19981216)81:12<2270::AID-HLCA2270>3.0.CO;2-#

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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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Lochner, Martin

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

0018-019X

Publisher:

Verlag Helvetica Chimica Acta

Language:

English

Submitter:

Martin Lochner

Date Deposited:

19 Dec 2014 11:16

Last Modified:

19 Dec 2014 11:17

Publisher DOI:

10.1002/(SICI)1522-2675(19981216)81:12<2270::AID-HLCA2270>3.0.CO;2-#

BORIS DOI:

10.7892/boris.60965

URI:

https://boris.unibe.ch/id/eprint/60965

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