Amino Derivatives of Strophanthidin. I. Reactions of Primary and Secondary Amines with the Butenolide Side Chain of Strophanthidin<sup>1</sup>

Bembry, Thomas H.; Elderfield, Robert C.; Krueger, Geraldine L.

doi:10.1021/jo01077a025

Cited by 6 publications

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“…Thus strophanthidin reacts with primary and secondary amines to form nitrogenous derivatives (Bembry, Elderfield and Krueger, 1960), one of which, tryptamine-strophanthidin, not only retains a typical digitalis-like action on the isolated papillary muscle of the cat (Greiner and Reilly, 1952), but unlike the glycosides of the strophanthus series, it is active by the oral route in man (Otto and others, 1953). Unfortunately, however, it often produces emesis.…”

Section: IXmentioning

confidence: 99%

Biological Activity in Steroids Possessing Nitrogen Atoms

Alauddin

Martin‐Smith

1962

Journal of Pharmacy and Pharmacology

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Section: IXmentioning

confidence: 99%

Biological Activity in Steroids Possessing Nitrogen Atoms

Alauddin

Martin‐Smith

1962

Journal of Pharmacy and Pharmacology

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“…Their structural fragments are present in such natural substances as porphyrins, bile pigments (biliverdin, phycocyanobilin), natural alkaloids (lilidine 1, Jatropha macrorrhiza, Mirabimides A-D 2) and also in compounds having antibiotic [Malonomicin (3)] and pharmacological activity. Among the antimetabolites, antibacterial agents, and enzymes, including inhibitors, there are substances containing a pyrrol-2-one ring: a-Lipomycin 4 and streptolydigin, which inhibits the synthesis of RNA by the bacterium Bacillus megaterium, thereby retarding their development [44,45].…”

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Reactivity of pyrrol-2-ones. (review)

Egorova

Timofeeva

2004

Chem Heterocycl Compd

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Published data on the chemical transformations of pyrrol-2-ones are reviewed and analyzed. The extensive synthetic possibilities of compounds containing a pyrrolone ring in the synthesis of various heterocyclic compounds with complex structures are demonstrated. The reactions are arranged according to the reaction centers of the pyrrol-2-ones: The methylene unit, the C=C double bond, the electron-deficient carbon atom of the carbonyl group.

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Lactone, 14. Mitt.: Synthese lactonverbrückter 1,1‐Diarylethylamine

Lehmann

Gossen

1987

Archiv der Pharmazie

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Umsetzung der 5,5-0iaryl-2(5H)-furanone 4a-d mit überschüssigen Aminen liefert Aminoamide 5a-k, die durch Hydrolyse und Ringschluß in die gewünschten 4-Amino-5,5-diaryl-4,5-dihydro-2(3H)-furanooe 6a-k überführt werden. Lactones, XIV: Synthesis of Lactone-Bridged l,l-DiarylethanaminesReaction of the 5,5-diaryl-2(5H)-furanones 4a-d with excess of amines gives the amino amides 5a-k, which are transformed into the desired 4-amino-5,5-diaryl-4,5-dihydro-2(3H)-furanones 6a-k by hydrolysis and ring closure. Ein wesentlicher Parameter in der Struktur-Wirkungs-Beziehung bei Pharmaka mit Diarylalkylamin-Struktur ist die Länge der Alkylkette. Im Rahmen unserer Untersuchungen über lactonisierte Diarylalkylamine berichteten wir über Synthese und Pharmakologie von Derivaten mit 4 2 • 31 und 5 41 C-Atomen zwischen Aromaten und Aminogruppe. Um in dieser Reihe vollständigere Aussagen über Struktur-Wirkungs-Beziehungen machen zu können, sollte die Synthese diarylierter Aminolactone mit 2 C-Atomen zwischen Aromaten und Aminogruppe in Angriff genommen werden. Eine Möglichkeit sahen wir in der Addition von Aminen an ~a. ß-Butenolide des Typs 4, die nach Cannone et al. durch Grignardisierung des Diels-Alder-Adduktes I und anschließende thermische Spaltung zugänglich sind 51 • Aus bisher durchgeführten Umsetzungen von Aminen mit a, ß-ungesättigten Lactonen wie ß-Angelicalacton und Strophanthidin ergibt sich allerdings eine recht unübersichtliche Reaktivität. Michael-Addukte können nur selten rein isoliert werden, es überwiegt die Bildung von ungesättigten Hydroxyamiden, ungesättigten Aminosäuren, y-Imino-oder y-Enaminoamiden und -im Falle primärer Amine -Pyrrolioonen o -91 • Lehmann und GossenArch. Pharm.

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Amino Derivatives of Strophanthidin. I. Reactions of Primary and Secondary Amines with the Butenolide Side Chain of Strophanthidin¹

Cited by 6 publications

References 0 publications

Biological Activity in Steroids Possessing Nitrogen Atoms

Biological Activity in Steroids Possessing Nitrogen Atoms

Reactivity of pyrrol-2-ones. (review)

Lactone, 14. Mitt.: Synthese lactonverbrückter 1,1‐Diarylethylamine

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Amino Derivatives of Strophanthidin. I. Reactions of Primary and Secondary Amines with the Butenolide Side Chain of Strophanthidin1

Cited by 6 publications

References 0 publications

Biological Activity in Steroids Possessing Nitrogen Atoms

Biological Activity in Steroids Possessing Nitrogen Atoms

Reactivity of pyrrol-2-ones. (review)

Lactone, 14. Mitt.: Synthese lactonverbrückter 1,1‐Diarylethylamine

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Amino Derivatives of Strophanthidin. I. Reactions of Primary and Secondary Amines with the Butenolide Side Chain of Strophanthidin¹