A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2018-10-04

AUTHORS

Kostiantyn P. Melnykov, Dmitriy M. Volochnyuk, Sergey V. Ryabukhin, Eduard B. Rusanov, Oleksandr O. Grygorenko

ABSTRACT

An approach to rel-(4aS,6R,7aR)-octahydro-1H-cyclopenta[b]pyridine-6-carboxylic acid—a bicyclic conformationally restricted γ-aminobutyric acid (GABA) analogue was developed. The eight-step sequence relied on the reaction of 2,3-bis(chloromethyl)pyridine and a C1-binucleophile and the catalytic reduction of the pyridine ring as the key steps and allowed for the preparation of the title compound in 9.0% overall yield. Assessment of the octahydro-1H-cyclopenta[b]pyridine scaffold geometry showed that this template can be considered truly three-dimensional. More... »

PAGES

255-261

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00726-018-2660-1

DOI

http://dx.doi.org/10.1007/s00726-018-2660-1

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1107399333

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30288603


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184 grid-institutes:grid.464621.3 schema:alternateName Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, 02660, Kyiv, Ukraine
185 schema:name Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, 02660, Kyiv, Ukraine
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