Regioselective synthesis and properties of 3-cyano-6-thienylpyridine-2(1H)-thiones

Moryashova, S. I.; Salamandra, L. K.; Fedorov, A. E.; Rodinovskaya, L. A.; Shestopalov, A. M.; Семенов, В. В.

doi:10.1007/bf02498968

Cited by 8 publications

(2 citation statements)

References 3 publications

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“…One of the main directions of the use of thioamide 1 is the preparation of a wide range of S,Nheterocyclic compounds, the most important of which are 3-cyanopyridine-2(1H)-thiones 2 [5][6][7][8][9][10][11] (Scheme 1). Compounds 2 are a convenient scaffolds for the synthesis of a wide range of thieno [2,3-b]pyridines [12][13][14][15][16][17][18][19][20], thiazolo [3,2-a]pyridines [21][22][23][24][25][26][27][28][29], pyrido [2,1-b] [1,3,5]thiadiazines [30 -34], dipyrido[1,2-a:1'2'-e] [1,3,5,7]tetrazocines [35], pyrido [1,2-a] [1,3,5] triazines [36], isothiazolo [5,4-b]pyridines [37][38][39][40], and other bi-and polycyclic structures.…”

Section: Doi: 101134/s107036322102002xmentioning

confidence: 99%

Synthesis and Analgesic Activity of New Heterocyclic Cyanothioacetamide Derivatives

Bibik

Dotsenko

et al. 2021

Russ J Gen Chem

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The reaction of cyanothioacetamide with aromatic aldehydes and 1,3-dicarbonyl compounds followed by aminomethylation or S-alkylation gave a series of heterocyclic derivatives with a 1,2,3,4-tetrahydropyridine or 1,4,5,6,7,8-hexahydroquinoline fragment. The resulting compounds were tested for analgesic activity in vivo. Some of the prepared compounds showed an antinociceptive effect superior to that of ketorolac in dynamics.

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Section: Doi: 101134/s107036322102002xmentioning

confidence: 99%

Synthesis and Analgesic Activity of New Heterocyclic Cyanothioacetamide Derivatives

Bibik

Dotsenko

et al. 2021

Russ J Gen Chem

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“…В первую очередь цианотиоацетамид 1 нашел применение в синтезе важных полупродуктов тонкого органического синтеза -2-меркапто(2тиоксо)никотинонитрилов и родственных им 3-цианопиридин-2-тиолатов [5][6][7][8][9][10][11][12]. Такие соединения, в свою очередь, активно используются в дальнейших гетероциклизациях в производные тиено [2,3-b]пиридина [13][14][15][16][17][18][19][20][21], тиазоло [3,2-а]пиридина [22][23][24][25][26][27][28][29][30], изотиазоло [5,4-b]пиридина [31][32][33][34], пиридо [2,1-b] [1,3,5]тиадиазина [35][36][37][38][39] и ряда других гетероциклических структур.…”

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Synthesis, anti-exudative and anti-inflammatory properties of substituted N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-1,4-dihydropyridin-3-carboxamides

Oleinik,

Bibik,

Dotsenko

et al. 2023

Chem

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One-pot reaction of cyanothioacetamide, N-(2,4-dichlorophenyl)acetoacetamide and furfural in the presence of excessive N-methylmorpholine in EtOH at 25 °C gives N-methylmorpholinium 5-[(2,4-dichlorophenyl)carbamoyl]-3-cyano-4-(2-furyl)-6-methyl-1,4-dihydropyridin-2-thiolate, yielding 82%. Subsequent S-alkylation of the prepared thiolate with N-substituted α-chloroacetamides occurs in a regiospecific way to form N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-6-[(2-oxo-2-{[substituted aryl]amino}ethyl)sulfanyl]-1,4-dihydropyridin-3-carboxamides 10–17. Compounds 10–17 were identified by means of IR and NMR spectroscopy, as well as by elemental analysis. Synthesized compounds 10–17 were examined for anti-exudative and anti-inflammatory activity. White laboratory rats numbering 112 individuals were divided into control (“acute formalin-induced paw edema”) and intact groups, 4 reference groups (acetylsalicylic acid, indomethacin, nimesulide, and paracetamol) and 8 experimental groups, according to the number of tested 1,4-dihydropyridine derivatives. The efficacy of the anti-inflammatory activity of the samples was evaluated in the model of “acute formalin paw edema” in rats, which was simulated by injecting 0.1 mL of 2% formalin solution into the aponeurosis of the right hind limb. The studied compounds were given intragastrically at a dose of 5 mg/kg 1.5 hours before the induction of the inflammatory process. Oncometric changes were measured quantitatively by limb girth. It was shown that the most pronounced anti-inflammatory activity was possessed by: N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-6-[(2-oxo-2-{[3-(trifluoromethyl)phenyl]-amino}ethyl)sulfanyl]-1,4-dihydropyridin-3-carboxamide 12 (1.09–1.81 times more effective than the reference drugs); 6-[(2-anilino-2-oxoethyl)sulfanyl]- N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-1,4-dihydropyridin-3-carboxamide 16, which reduced the induced paw edema by 42.91% compared to control; N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-6-({2-[(3-methylphenyl)amino]-2-oxoethyl}sulfanyl)-1,4-dihydropyridin-3-carboxamide 14 (1.65–2.85 times higher anti-inflammatory activity compared to the reference drugs in 18-hour experiments). N-(2,4-Dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-6-({2-[(3,5-dimethylphenyl)amino]-2-oxoethyl}sulfanyl)-1,4-dihydropyridin-3-carboxamide 11 was found to be the most active, reducing paw edema 2.9 times more effectively than nimesulide

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Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure–activity relationships

Hayakawa¹,

Shioya²,

Agatsuma

et al. 2004

Bioorganic & Medicinal Chemistry Letters

118

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Regioselective synthesis and properties of 3-cyano-6-thienylpyridine-2(1H)-thiones

Cited by 8 publications

References 3 publications

Synthesis and Analgesic Activity of New Heterocyclic Cyanothioacetamide Derivatives

Synthesis and Analgesic Activity of New Heterocyclic Cyanothioacetamide Derivatives

Synthesis, anti-exudative and anti-inflammatory properties of substituted N-(2,4-dichlorophenyl)-5-cyano-4-(2-furyl)-2-methyl-1,4-dihydropyridin-3-carboxamides

Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure–activity relationships

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