6975-44-6

Basic information

• Product Name: 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER
• Synonyms: 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER;4,6-DIHYDROXYPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;BUTTPARK 153\57-32;SPECS AC-907/34126052;Ethyl 4,6-dihydroxynicotinate;4,6-Dihydroxynicotinic acid ethyl ester ,97%;NSC 22486;2,4-Dihydroxy-5-(ethoxycarbonyl)pyridine
• CAS NO: 6975-44-6
• Molecular Formula: C₈H₉NO₄
• Molecular Weight: 183.16
• Product Categories: Pyridine
• Mol File: 6975-44-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 214-217°
• Boiling Point: 497.628 °C at 760 mmHg
• Flash Point: 254.757 °C
• Appearance: /
• Density: 1.380
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER(6975-44-6)
• EPA Substance Registry System: 4, 6-DIHYDROXYNICOTINIC ACID ETHYL ESTER(6975-44-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 6975-44-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Ethyl 4,?6-?dihydroxynicotinate has been used as a reactant is the synthesis of pyridazinopyrimidinone and pyridopyrimidinone derivatives as PDE5 inhibitors and for the synthesis of pyridone diaryl ether non-nucleoside inhibitors of HIV-1 reverse transcriptase.

InChI:InChI=1/C8H9NO4/c1-2-13-8(12)5-4-9-7(11)3-6(5)10/h3-4H,2H2,1H3,(H2,9,10,11)

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 108-24-7 acetic anhydride 
• 1336-21-6 ammonium hydroxide 
• 149-73-5 trimethyl orthoformate 
• 570-08-1 diethyl acetylmalonate 
• 64-19-7 acetic acid 

Downstream Products

• 5466-62-6 4,6-dihydroxy-nicotinic acid 
• 40296-46-6 ethyl 4,6-dichloronicotinate 
• 846541-71-7 ethyl 5-chloro-4,6-dihydroxynicotinate 
• 6317-97-1 ethyl 2,4-dihydroxy-3-nitropyridine-5-carboxylate 
• 107836-75-9 4,6-dichloropyridine-3-carbonyl chloride 
• 1012878-94-2 ethyl 6-chloro-4-(phenylamino)nicotinate 
• 1445151-21-2 N-ethyl-6-(3-ethylureido)-4-(phenylamino)nicotinamide 
• 1445151-22-3 N-(2-chIorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide 
• 1445151-23-4 6-(3-ethylureido )-N-(1-methyl-1H-pyrazol-5-yl)-4-(phenylamino)nicotinamide 
• 1445151-24-5 6-(3-ethylureido)-4-(phenylamino)-N-(2-(trifluoromethyl)phenyl)nicotinamide 
• 1445151-25-6 ethyl (2E)-3-{4-[({6-[(ethylcarbamoyl)amino]-4-(phenylamino)pyridin-3-yl}carbonyl)amino]phenyl}prop-2-enoate 
• 1445151-96-1 6-(3-ethylureido)-N-methoxy-N-methyl-4-(phenylamino)nicotinamide 
• 1445152-25-9 1-(5-benzoyl-4-(phenylamino)pyridin-2-yl)-3-ethylurea 
• 1445151-74-5 6-(3-ethylureido)-4-(phenylamino)nicotinamide 

Relevant articles and documents

Quinolone amides as antitrypanosomal lead compounds with In Vivo activity

Human African trypanosomiasis (HAT) is a major tropical disease for which few drugs for treatment are available, driving the need for novel active compounds. Recently, morpholino-substituted benzyl amides of the fluoroquinolone-type antibiotics were identified to be compounds highly active against Trypanosoma brucei brucei. Since the lead compound GHQ168 was challenged by poor water solubility in previous trials, the aim of this study was to introduce structural variations to GHQ168 as well as to formulate GHQ168 with the ultimate goal to increase its aqueous solubility while maintaining its in vitro antitrypanosomal activity. The pharmacokinetic parameters of spray-dried GHQ168 and the newly synthesized compounds GHQ242 and GHQ243 in mice were characterized by elimination half-lives ranging from 1.5 to 3.5 h after intraperitoneal administration (4 mice/compound), moderate to strong human serum albumin binding for GHQ168 (80%) and GHQ243 (45%), and very high human serum albumin binding (>99%) for GHQ242. For the lead compound, GHQ168, the apparent clearance was 112 ml/h and the apparent volume of distribution was 14 liters/kg of body weight (BW). Mice infected with T. b. rhodesiense (STIB900) were treated in a stringent study scheme (2 daily applications between days 3 and 6 postinfection). Exposure to spray-dried GHQ168 in contrast to the control treatment resulted in mean survival durations of 17 versus 9 days, respectively, a difference that was statistically significant. Results that were statistically insignificantly different were obtained between the control and the GHQ242 and GHQ243 treatments. Therefore, GHQ168 was further profiled in an early-treatment scheme (2 daily applications at days 1 to 4 postinfection), and the results were compared with those obtained with a control treatment. The result was statistically significant mean survival times exceeding 32 days (end of the observation period) versus 7 days for the GHQ168 and control treatments, respectively. Spray-dried GHQ168 demonstrated exciting antitrypanosomal efficacy.

Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity

The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented,

Discovery and SAR study of 2-(1-propylpiperidin-4-yl)-3H-imidazo[4,5-c]pyridine-7-carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase-1 (PARP-1) for the treatment of cancer

A series of imidazo[4,5-c]pyridine-7-carboxamide derivatives as poly(ADP-ribose) polymerase (PARP) inhibitors have been developed. All target compounds were evaluated for their PARP-1 inhibitory activity and some were further assessed for cellular potency