113858-92-7

Basic information

• Product Name: ETHYL 5-CYANO-6-MERCAPTO-2-PHENYLNICOTINATE
• Synonyms: ETHYL 5-CYANO-6-MERCAPTO-2-PHENYLNICOTINATE;ETHYL 3-CYANO-2-MERCAPTO-6-PHENYLPYRIDINE-5-CARBOXYLATE
• CAS NO: 113858-92-7
• Molecular Formula: C₁₅H₁₂N₂O₂S
• Molecular Weight: 284.33298
• Mol File: 113858-92-7.mol

Chemical Properties

• Boiling Point: 403.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 5.95±0.70(Predicted)
• CAS DataBase Reference: ETHYL 5-CYANO-6-MERCAPTO-2-PHENYLNICOTINATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-CYANO-6-MERCAPTO-2-PHENYLNICOTINATE(113858-92-7)
• EPA Substance Registry System: ETHYL 5-CYANO-6-MERCAPTO-2-PHENYLNICOTINATE(113858-92-7)

Safety Data

• Hazardous Substances Data: 113858-92-7(Hazardous Substances Data)

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 39973-76-7 ethyl 2-benzoyl-3-ethoxyacrylate 

Downstream Products

• 113858-98-3 5-Cyano-6-methylsulfanyl-2-phenyl-nicotinic acid ethyl ester 
• 113859-04-4 5-Hydroxymethyl-2-methylsulfanyl-6-phenyl-nicotinonitrile 
• 113859-28-2 (2,4-Diamino-7-phenyl-pyrido[2,3-d]pyrimidin-6-yl)-methanol 
• 113859-10-2 5-Methoxymethoxymethyl-2-methylsulfanyl-6-phenyl-nicotinonitrile 
• 113859-22-6 6-Methoxymethoxymethyl-7-phenyl-pyrido[2,3-d]pyrimidine-2,4-diamine 
• 113859-16-8 2-Methanesulfonyl-5-methoxymethoxymethyl-6-phenyl-nicotinonitrile 
• 113859-38-4 N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 113859-33-9 diethyl N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamate 

Relevant articles and documents

Synthesis of 1-(β-D-glycopyranosyl)-3-deazapyrimidines from 2-hydroxy and 2-mercaptopyridines

The synthesis of new 4- and 5-substituted-3-cyanopyridine nucleosides has been performed by reacting the silylated pyridines and penta-O-aeetyl-α -Dglycopyranose in dichloroethane in the presence of SnCl4. The free nucleosides were tested for their potential activity against HIV and different types of tumor.

Chemical synthesis and biological activities of 5-deazaaminopterin analogues bearing substituent(s) at the 5- and/or 7-position(s)

Condensation of cyanothioacetamide (4) with ethyl α-(ethoxymethylene)acetoacetate (5b), ethyl 4-ethoxy-2-(ethoxymethylene)-3-oxobutanoate (5c), ethyl 2-(ethoxymethylene)-3-oxo-4-phenylpropanoate (5d) afforded exclusively the corresponding 6-substituted pyridines (6b-d). Cyclization of 4 with 3-carbethoxybutane-2,4-dione (5e) gave 3-cyano-5-(ethoxycarbonyl)-4,6-dimethylpyridine-2(1H)-thione (6e), whereas reaction of 4 with 3-carbethoxy-1-phenylpropane-1,3-dione (5f) yielded two products, 3-cyano-5-(ethoxycarbonyl)-4-methyl-6-phenylpyridine-2(1H)-thione (6f) and the 6-methyl-4-phenyl isomer 6g. The structural assignments for 6f and 6g are made on the basis of 1H and 13C NMR spectral analyses of the 2-(methylthio)nicotinates (7f,g) prepared from 6f and 6g by treatment with MeI/K2CO3. Nicotinates 7b,d-g were converted into their corresponding 2,4-diaminopyrido[2,3-d]pyrimidines 12b,d-g in five steps, via reduction, protection, oxidation, condensation with guanidine, and deprotection. The 7-mono- and 5,7-disubstituted-5-deazaaminopterins (1b,d-g) were prepared from the respective pyrido[2,3-d]pyrimidines 12b,d-g. Preliminary biological studies showed that 7-methyl and 5,7-dimethyl analogues (1b and 1e) were less active than methotrexate against human leukemic HL-60 and murine L-1210 cells in tissue culture. Compound 1e produced and ILS of 71% at 100 mg/kg per day x 5 (ip) in BDF mice inoculated ip with 106 L-1210 cells.