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6-(1H-IMIDAZOL-1-YL)NICOTINIC ACID - CAS 216955-75-8

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Category
Main Product
Product Name
6-(1H-IMIDAZOL-1-YL)NICOTINIC ACID
Catalog Number
216955-75-8
Synonyms
6-(1H-IMIDAZOL-1-YL)NICOTINIC ACID;6-IMIDAZOL-1-YL-NICOTINIC ACID
CAS Number
216955-75-8
Molecular Weight
189.17
Molecular Formula
C9H7N3O2
COA
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MSDS
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Canonical SMILES
C1=CC(=NC=C1C(=O)O)N2C=CN=C2
InChI
InChI=1S/C9H7N3O2/c13-9(14)7-1-2-8(11-5-7)12-4-3-10-6-12/h1-6H,(H,13,14)
InChIKey
HHWABXGAQNCVFW-UHFFFAOYSA-N
Structure
CAS 216955-75-8 6-(1H-IMIDAZOL-1-YL)NICOTINIC ACID
Specification
Purity
95%
Boiling Point
442.5ºC at 760mmHg
Melting Point
>270ºC
Density
1.39g/cm3
Reference Reading
1.Discovery of (S)-6-(3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamido)nicotinic acid as a hepatoselective glucokinase activator clinical candidate for treating type 2 diabetes mellitus.
Pfefferkorn JA1, Guzman-Perez A, Litchfield J, Aiello R, Treadway JL, Pettersen J, Minich ML, Filipski KJ, Jones CS, Tu M, Aspnes G, Risley H, Bian J, Stevens BD, Bourassa P, D'Aquila T, Baker L, Barucci N, Robertson AS, Bourbonais F, Derksen DR, Macdougall M, Cabrera O, Chen J, Lapworth AL, Landro JA, Zavadoski WJ, Atkinson K, Haddish-Berhane N, Tan B, Yao L, Kosa RE, Varma MV, Feng B, Duignan DB, El-Kattan A, Murdande S, Liu S, Ammirati M, Knafels J, Dasilva-Jardine P, Sweet L, Liras S, Rolph TP. J Med Chem. 2012 Feb 9;55(3):1318-33. doi: 10.1021/jm2014887. Epub 2012 Jan 24.
Glucokinase is a key regulator of glucose homeostasis, and small molecule allosteric activators of this enzyme represent a promising opportunity for the treatment of type 2 diabetes. Systemically acting glucokinase activators (liver and pancreas) have been reported to be efficacious but in many cases present hypoglycaemia risk due to activation of the enzyme at low glucose levels in the pancreas, leading to inappropriately excessive insulin secretion. It was therefore postulated that a liver selective activator may offer effective glycemic control with reduced hypoglycemia risk. Herein, we report structure-activity studies on a carboxylic acid containing series of glucokinase activators with preferential activity in hepatocytes versus pancreatic β-cells. These activators were designed to have low passive permeability thereby minimizing distribution into extrahepatic tissues; concurrently, they were also optimized as substrates for active liver uptake via members of the organic anion transporting polypeptide (OATP) family.
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