Isolation and structural elucidation of a new sildenafil analogue from a functional coffee View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2013-05

AUTHORS

Lin Li, Min-Yong Low, Xiaowei Ge, Bosco C. Bloodworth, Hwee-Ling Koh

ABSTRACT

A sildenafil analogue was detected in a functional coffee sample labelled to have male sexual performance enhancement effects. This analogue was isolated and purified by flash chromatography and preparative high-performance liquid chromatography. Its structure was elucidated using high-resolution mass spectrometry; electrospray ionization-tandem mass spectrometry; and nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, and infrared spectroscopy. Compared with sildenafil, instead of an N-methylpiperazinyl moiety, ring opening of the piperazine ring with the loss of a carbon atom resulted in a substituted benzenesulfonamide. The chemical name of this analogue is N-[2-(dimethylamino)ethyl]-4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonamide. It is named descarbonsildenafil because it has one less carbon atom when compared with sildenafil. More... »

PAGES

4443-4450

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00216-012-6236-8

DOI

http://dx.doi.org/10.1007/s00216-012-6236-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1051476548

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/22825675


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