1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylicacid

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid is from Cordyceps bassiana, which is one of Cordyceps species with anti-oxidative, anti-cancer, anti-inflammatory, anti-diabetic, anti-obesity, anti-angiogenic, and anti-nociceptive activities. 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid targets to block AP-1-mediated luciferase activity, implying it has an anti-inflammatory function[1].

A suspension of sodium hydride (2.70 g, 67.50 mmol) in methanol (60 ml.) was stirred under nitrogen atmosphere at room temperature for 5 min. 6-hydroxynicotinic acid (4.70 g, 33.79 mmol) was added, the mixture was stirred at 6O0C for 30 min and then methyl iodide (8.4 mL, 134.93 mmol) was added and the reaction mixture was tirred at 6O0C overnight. 2N sodium hydroxide (20 mL) was added and the mixture was tirred at 6O0C for 30 min. The solvent was evaporated under vacuum, water (200 mL) was added to the residue and it was acidified with 2N hydrochloric acid. The solid was filtered, washed with water and dried and the filtrate was extracted with diethyl ether, dried, filtered and evaporated under vacuum. The resulting crude altogether with the solid was triturated with isopropyl alcohol, filtered, washed with hexanes and dried to give 3.58 g (69percent) of the title compound as a solid. LRMS: m/z 154(M+1 )+ Retention time: 1.58min (method A)1 H NMR (200 MHz, DMSO-c/6) delta ppm 3.49 (s, 3 H) 6.40 (d, J=9.76 Hz, 1 H) 7.78 (dd, J=9.57, 2.54 Hz, 1 H) 8.48 (d, J=2.34 Hz, 1 H) 12.78 (br. s., 1 H)EXAMPLE 23 1-Methyl-6-keto-1, 6-dihydronicotinic acid 1percent cream is prepared as follows. 1-Methyl-6-keto-1, 6-dihydronicotinic acid 1 g synthesised according to Example 19 is dissolved with 10 ml of 2-pyrrolidinone, and the solution is admixed with 89 g of hydrophillic ointment USP. Mixing is continued until a uniform consistency is obtained.General procedure: 1 , 5-Dimethyl-6-oxo- 1 , 6-dihydro-pyridine-3-carboxylic acid D- 1 1, 5 -Dimethyl-6-oxo- 1 , 6-dihydro-pyridine-3 -carboxylic acid methyl ester C-i(2.600 g; 14.350 mmol) is suspended in MeOH. Sodium hydroxide (1 M solution, 45.000 ml; 45.000 mmol) is added and the reaction mixture is heated up to 100°C(Drysyn, reflux) for 2 h. MeOH is removed under reduced pressure and iN HC1(46 ml) is added to the solution, precipitation occurs. The precipitate is filtered offand dried under reduced pressure.Yield: 98percent (2.34 g; 14.00 mmol)

A metabolite of Tryptophan-niacin.

Molecular Weight:153.14
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:57.6
Heavy Atom Count:11
Complexity:265
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes