Journal ArticleDOI
Dimethylamine substitution in N,N-dimethyl enamines. Synthesis of aplysinopsin analogues and 3-aminotetrahydrocoumarin derivatives
Lovro Selic,Branko Stanovnik +1 more
TLDR
Some new six-membered aplysinopsin analogues were prepared from 5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetriones and indole derivatives as discussed by the authors.About:
This article is published in Tetrahedron.The article was published on 2001-04-09. It has received 41 citations till now. The article focuses on the topics: Dimethylamine & Indole test.read more
Citations
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Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones.
Branko Stanovnik,Jurij Svete +1 more
Journal ArticleDOI
Application of alkyl 3-dimethylamino-2-(1H-indol-3-yl)propenoates in the synthesis of 3-heteroarylindoles
TL;DR: In this article, N,N-dimethylenaminones with α-heteroarylamines were obtained in poor to moderate yields, while intramolecular condensations with C,O-1,3-dinucleophiles furnished condensed indolylpyranones.
Journal ArticleDOI
A simple synthesis of aplysinopsin analogues by dimethylamine substitution in N,N-(dimethylamino)methylidene derivatives of five-membered heterocycles
TL;DR: In this paper, aplysinopsin analogues were prepared by a simple coupling of N, N -(dimethylamino)methylidene substituted hydantoin, thiohydantoin and thiazolone derivatives, with indole derivatives.
Journal ArticleDOI
[2+2] Cycloaddition of electron-poor acetylenes to (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones: synthesis of highly functionalized 1-heteroaroyl-1,3-butadienes
Jure Bezenšek,Tanja Kolesa,Uroš Grošelj,Jernej Wagger,Katarina Stare,Anton Meden,Jurij Svete,Branko Stanovnik +7 more
TL;DR: Microwave-assisted cycloaddition of (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1ones to dimethyl acetylenedicarboxylates gives (2E,3E)-dimethyl-2-[(dimethyamino)methylene]-3-(substituted)succinates in 8-91% yield as mentioned in this paper.
Journal ArticleDOI
Synthesis of (S,Z)-3-[(1H-indol-3-yl)methylidene]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one: an alternative, enaminone based, route to unsaturated cyclodipeptides
TL;DR: A series of racemic and enantiopure (S,Z)-3-[(1H-indol-3-yl)methylidene]hexahydropyrrolo[1,2-a]pyrazin-4 (1H)-one (cyclic Pro-ΔTrp) dipeptide analogues were prepared by direct coupling of cyclic cyclodipeptide enaminone (R,S)-5 with various indole derivatives as mentioned in this paper.
References
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Journal ArticleDOI
Aplysinopsin, a new tryptophan derivative from a sponge
Journal ArticleDOI
Novel Aplysinopsin‐Type Alkaloids from Scleractinian Corals of the Family Dendrophylliidae of the Mediterranean and the Philippines. Configurational‐assignment criteria, stereospecific synthesis, and photoisomerization
TL;DR: Condensations of indol-3-carboxaldehyde or of its 6-bromo derivative 14 with hydantoin or 3-methylhydantoin, or 1,3dimethylHydantoin give the prevalent natural aplysinopsins with high stereospecificity.
Journal ArticleDOI
Aplysinopsin-type alkaloids from Dendrophyllia sp., a scleractinian coral of the family dendrophylliidae of the philippines, facile photochemical (Z/E) photoisomerization and thermal reversal
TL;DR: The dendrophylliid DENDrophyllia sp.
Journal ArticleDOI
Metabolites of the marine sponge Dercitus species
Peter Djura,D. John Faulkner +1 more
Aplysinopsin: antineoplastic tryptophan derivative from the marine sponge Verongia spengelii.
Hollenbeak Kh,Schmitz Fj +1 more
TL;DR: Bioassay-guided fractionation of the aqueous alcoholic extract of the marine sponge Verongia spengelii for tumor inhibitory agents led to the isolation of aplysinopsin, a new tryptophan derivative recently reported from another sponge Thorecta aply sinopsis.
Related Papers (5)
Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones.
Branko Stanovnik,Jurij Svete +1 more