4,6-Dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile

Eyduran, Fatih; Özyürek, Cengiz; Dilek, Nefise; Ískeleli, Nazan Ocak; Şendil, Kıvılcim

doi:10.1107/s1600536807016418

Cited by 9 publications

(11 citation statements)

References 7 publications

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“…3), with the maximum deviations of -0.068 (6) Å for N4 in molecule A and 0.079 (6) Å for N2A in molecule B. The bond lengths of molecules A and B are comparable to those of the previously published structures (Eyduran et al, 2007;Allen et al, 1987). Fig.…”

Section: S1 Commentsupporting

confidence: 77%

“…For the use of 3-cyanopyridine-2(1H)-thiones in the synthesis of bio-active compounds, see: Taylor et al (1983); Gangiee et al (1991); Amr et al (2003); Abu-Shanab et al (2002); Awad et al (1962); El-Gaby (2004); Miky & Zahkoug (1997;Guerrera et al (1993); Krauze et al (1999). For a similar crystal structure, see: Eyduran et al (2007). For the synthesis of the title compound, see: Abu-Shanab (1999).…”

Section: Related Literaturementioning

confidence: 99%

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Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

et al. 2014

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Section: S1 Commentsupporting

confidence: 77%

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

et al. 2014

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“…The general synthesis for the target thieno[2,3- b ]pyridine structures ( 1 ) is illustrated in Scheme . Synthesis of the key pyridinethione core (4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile, 5 ) was furnished by a condensation reaction between acetylacetone ( 3 ) and 2-cyanothioacetamide ( 4 ) and isolated in good yield. The chloroacetamide derivatives 8a – q were synthesized in good to excellent yield in accordance with literature, whereby chloroacetyl chloride ( 6 ) was reacted with the appropriately substituted benzylamine ( 7a – q ).…”

Section: Resultsmentioning

confidence: 99%

Probing Structural Requirements of Positive Allosteric Modulators of the M₄ Muscarinic Receptor

et al. 2013

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The M4 mAChR is implicated in several CNS disorders and possesses an allosteric binding site for which ligands modulating the affinity and/or efficacy of ACh may be exploited for selective receptor targeting. We report the synthesis of a focused library of putative M4 PAMs derived from VU0152100 and VU10005. These compounds investigate the pharmacological effects of previously identified methoxy and fluoro substituents, providing useful estimates of affinity (KB), cooperativity (αβ), and direct agonist properties (τB).

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“…Within these, two aspects were analysed, the first addressing the preferred crystal packing and the second investigating the involvement of the cyano group in the hydrogen-bonding pattern. In ERISIH (Rybakov et al, 2004) and YIBZAL (Eyduran et al, 2007) A partial packing diagram for (3). Only H atoms which participate in hydrogen bonds are shown.…”

Section: Tablementioning

confidence: 99%

3-Cyano-6-hydroxy-4-methyl-2-pyridone: two new pseudopolymorphs and two cocrystals with products of anin situnucleophilic aromatic substitution

Gerhardt

Bolte

2015

Acta Crystallogr C

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Four crystal structures of 3-cyano-6-hydroxy-4-methyl-2-pyridone (CMP), viz. the dimethyl sulfoxide monosolvate, C7H6N2O2·C2H6OS, (1), the N,N-dimethylacetamide monosolvate, C7H6N2O2·C4H9NO, (2), a cocrystal with 2-amino-4-dimethylamino-6-methylpyrimidine (as the salt 2-amino-4-dimethylamino-6-methylpyrimidin-1-ium 5-cyano-4-methyl-6-oxo-1,6-dihydropyridin-2-olate), C7H13N4(+)·C7H5N2O2(-), (3), and a cocrystal with N,N-dimethylacetamide and 4,6-diamino-2-dimethylamino-1,3,5-triazine [as the solvated salt 2,6-diamino-4-dimethylamino-1,3,5-triazin-1-ium 5-cyano-4-methyl-6-oxo-1,6-dihydropyridin-2-olate-N,N-dimethylacetamide (1/1)], C5H11N6(+)·C7H5N2O2(-)·C4H9NO, (4), are reported. Solvates (1) and (2) both contain the hydroxy group in a para position with respect to the cyano group of CMP, acting as a hydrogen-bond donor and leading to rather similar packing motifs. In cocrystals (3) and (4), hydrolysis of the solvent molecules occurs and an in situ nucleophilic aromatic substitution of a Cl atom with a dimethylamino group has taken place. Within all four structures, an R2(2)(8) N-H...O hydrogen-bonding pattern is observed, connecting the CMP molecules, but the pattern differs depending on which O atom participates in the motif, either the ortho or para O atom with respect to the cyano group. Solvents and coformers are attached to these arrangements via single-point O-H...O interactions in (1) and (2) or by additional R4(4)(16) hydrogen-bonding patterns in (3) and (4). Since the in situ nucleophilic aromatic substitution of the coformers occurs, the possible Watson-Crick C-G base-pair-like arrangement is inhibited, yet the cyano group of the CMP molecules participates in hydrogen bonds with their coformers, influencing the crystal packing to form chains.

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4,6-Dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile

Abstract: In the crystal structure of the title compound, C8H8N2S, the molecules form centrosymmetric dimers via N—H...S hydrogen bonds.

Cited by 9 publications

References 7 publications

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

Probing Structural Requirements of Positive Allosteric Modulators of the M₄ Muscarinic Receptor

3-Cyano-6-hydroxy-4-methyl-2-pyridone: two new pseudopolymorphs and two cocrystals with products of anin situnucleophilic aromatic substitution

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4,6-Dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile

Abstract: In the crystal structure of the title compound, C8H8N2S, the molecules form centrosymmetric dimers via N—H...S hydrogen bonds.

Cited by 9 publications

References 7 publications

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

Probing Structural Requirements of Positive Allosteric Modulators of the M4 Muscarinic Receptor

3-Cyano-6-hydroxy-4-methyl-2-pyridone: two new pseudopolymorphs and two cocrystals with products of anin situnucleophilic aromatic substitution

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Probing Structural Requirements of Positive Allosteric Modulators of the M₄ Muscarinic Receptor