Abstract

In the title compound, C25H25NO5S, which exhibits metabolism-regulating activity, the 1,4-di-hydro-pyridine ring adopts a flattened boat conformation while the cyclo-hexenone ring is in an envelope conformation. Mol-ecules in the crystal are assembled into C(6) chains along the a-axis direction via N-H⋯O hydrogen bonds. The thienyl fragment is disordered over two sets of sites in a 0.7220 (19):0.2780 (19) ratio.

Highlights

  • C25H25NO5S, which exhibits metabolism-regulating activity, the 1,4-dihydropyridine ring adopts a flattened boat conformation while the cyclohexenone ring is in an envelope conformation

  • Molecules in the crystal are assembled into C(6) chains along the a-axis direction via N—HÁ Á ÁO hydrogen bonds

  • A two-component disorder is found for the thienyl fragment, which assumes two orientations differing by a 180 rotation around the C7—C16 bond

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Summary

Chemical context

The 2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic esters in the class of condensed 1,4-dihydropyridine (DHP) derivatives have been relatively poorly studied. Monocyclic DHPs are very commonly known as cardiovascular regulating and hypotensive compounds (Swarnalatha et al, 2011). The title compound is an original substance with a specific ligand effect on the metabolismregulating free fatty acid receptor 3 (FFAR3 or GPR41). It does not act on other metabolite-sensing receptors such as FFAR2 (GPR43) or the hydroxycarboxylic receptor 2 (HCA2) having similar pharmacological effects

Structural commentary
Supramolecular features
Database survey
Metabolic activity
Synthesis and crystallization
Findings
Refinement
Full Text
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