4850-09-3

Usage

Uses

Used in Pharmaceutical Industry:
Neothiobinupharidine is used as a pharmaceutical compound for its potential therapeutic properties. The expression is: Neothiobinupharidine is used as a pharmaceutical compound for its potential therapeutic properties.
Used in Chemical Research:
In the field of chemical research, Neothiobinupharidine serves as a valuable subject for studying the properties and behavior of sulfur-containing alkaloids. The expression is: Neothiobinupharidine is used as a research subject for studying the properties and behavior of sulfur-containing alkaloids.
Used in Drug Development:
Due to its unique structure and properties, Neothiobinupharidine may be utilized in the development of new drugs targeting various health conditions. The expression is: Neothiobinupharidine is used as a potential drug candidate for the development of new medications.
Used in Crystallography:
The well-crystalline salts of Neothiobinupharidine, such as the dihydrobromide, diperchlorate, and methiodide forms, make it an interesting subject for crystallographic studies. The expression is: Neothiobinupharidine is used as a subject for crystallographic studies due to its well-crystalline salts.

References

Achmatowicz, Wrobel., Tetrahedron Lett., 129 (1964)Achmatowicz et ai., ibid, 927 (1964)Crystal structure: Birnbaum., Tetrahedron Lett., 4149 (1965)

Upstream product

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Relevant academic research and scientific papers

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.

Synthesis of (-)-neothiobinupharidine

An eight step, asymmetric synthesis of a dimeric thiaspirane nuphar alkaloid from 3-methyl-2-cyclo-pentenone is reported. The brevity of the route relies on a useful procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox manipulations and other functional group interconversions. The distribution of products that arise from spontaneous dimerization points to a more complex biosynthesis.