331466-74-1

Basic information

• Product Name: 2-phenyl-7-(2-thienyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one
• Synonyms: 2-phenyl-7-(2-thienyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one
• CAS NO: 331466-74-1
• Molecular Formula: C20H12F3N3OS2
• Molecular Weight: 431.4539896
• Mol File: 331466-74-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-phenyl-7-(2-thienyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-7-(2-thienyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one(331466-74-1)
• EPA Substance Registry System: 2-phenyl-7-(2-thienyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one(331466-74-1)

Safety Data

• Hazardous Substances Data: 331466-74-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 331466-63-8 3-amino-6-(2-thienyl)-4-trifluoromethylthienol[2,3-b]pyridine-2-carboxamide 
• 104960-50-1 4-(trifluoromethyl)-1,2-dihydro-6-(thiophen-2-yl)-2-thioxopyridine-3-carbonitrile 
• 88-15-3 2-Acetylthiophene 
• 299198-19-9 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridin-2-ylthioacetamide 
• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 

Relevant articles and documents

Discovery and structure-activity relationships study of thieno[2,3-b]pyridine analogues as hepatic gluconeogenesis inhibitors

Type 2 diabetes mellitus (T2DM) is a chronic, complex and multifactorial metabolic disorder, and targeting gluconeogenesis inhibition is a promising strategy for anti-diabetic drug discovery. This study discovered a new class of thieno[2,3-b]pyridine derivatives as hepatic gluconeogenesis inhibitors. First, a hit compound (DMT: IC50 = 33.8 μM) characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. Structure activity relationships (SARs) study showed that replaced the CF3 in the thienopyridine core could improve the potency and led to the discovery of 8e (IC50 = 16.8 μM) and 9d (IC50 = 12.3 μM) with potent inhibition of hepatic glucose production and good drug-like properties. Furthermore, the mechanism of 8e for the inhibition of hepatic glucose production was also identified, which could be effective through the reductive expression of the mRNA transcription level of gluconeogenic genes, including glucose-6-phosphatase (G6Pase) and hepatic phosphoenolpyruvate carboxykinase (PEPCK). Additionally, 8e could also reduce the fasting blood glucose and improve the oral glucose tolerance and pyruvate tolerance in db/db mice. The optimization of this class of derivatives had provided us a start point to develop new anti-hepatic gluconeogenesis agents.

Fluorine-containing heterocycles: Synthesis and some reactions of new 3-amino-2-functionalized-6-(2′-thienyl)-4-trifluoromethylthieno [2,3-b]pyridines

3-Cyano-6-(2′-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (2) was prepared and reacted with chloroacetone or phenacyl bromide to yield the 2-acetyl or benzoyl-3-amino-6-(2′-thienyl)-4-trifluoromethylthieno[2,3-b]pyridines (3a, b). In contrast, the reaction of 2 with chloroacetamide or its N-aryl derivatives gave the corresponding 2-carbamoylmethyl thiopyridines 4a-c. Upon treatment of these educts with K2CO3 or C2H5ONa in ethanol, they underwent intramolecular Thorpe-Ziegler cyclization to afford 3-amino-2-carbamoyl-6-(2′-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyrid ine (5a) and its N-aryl analogs 5b, c. Compounds 5a-c underwent some reactions to yield new pyrido[3',2':4,5]thieno[3,2-d]pyrimidines and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3] triazines.