1491169-09-5

Basic information

• Product Name: 2-cyano-3-(2-fluorophenyl)but-2-enoic acid ethyl ester
• Synonyms: 2-cyano-3-(2-fluorophenyl)but-2-enoic acid ethyl ester
• CAS NO: 1491169-09-5
• Molecular Weight: 233.242
• Mol File: 1491169-09-5.mol

Chemical Properties

• CAS DataBase Reference: 2-cyano-3-(2-fluorophenyl)but-2-enoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-3-(2-fluorophenyl)but-2-enoic acid ethyl ester(1491169-09-5)
• EPA Substance Registry System: 2-cyano-3-(2-fluorophenyl)but-2-enoic acid ethyl ester(1491169-09-5)

Safety Data

• Hazardous Substances Data: 1491169-09-5(Hazardous Substances Data)

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 1491169-19-7 2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-(2-fluorophenyl)pyridin-3-yl)methylamino)acetic acid methyl ester 
• 1491169-10-8 2-cyano-5-(dimethylamino)-3-(2-fluorophenyl)penta-2,4-dienoic acid ethyl ester 
• 1491169-12-0 3-(azidomethyl)-2-chloro-4-(2-fluorophenyl)pyridine 
• 877053-63-9 (2-chloro-4-(2-fluorophenyl)pyridin-3-yl)methanol 
• 1491169-11-9 2-chloro-4-(2-fluorophenyl)nicotinic acid ethyl ester 

Relevant articles and documents

Design, synthesis and biological evaluation of a novel class of potent TGR5 agonists based on a 4-phenyl pyridine scaffold

TGR5, a GPCR, is involved in energy and glucose homeostasis, and as such, is a target for the treatment of diabetes, obesity and other metabolic syndromes. A new class of TGR5 agonists based on a 4-phenyl pyridine scaffold was designed, synthesized and evaluated in vitro and in vivo. Extensive structure-activity relationship studies are reported herein. The most potent compounds 15a, 18b and 18c showed comparable activity with the lead compound 2. 15a had the best potency in vitro but displayed an unfavorable pharmacokinetic profile and was found to be ineffective during an oral glucose tolerance test in imprinting control region mice at a dose of 50 mg/kg.

Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.

Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists

Given its role in the mediation of energy and glucose homeostasis, the G-protein-coupled bile acid receptor1 (TGR5) is considered a potential target for the treatment of type2 diabetes mellitus and other metabolic disorders. By thorough analysis of diverse structures of published TGR5 agonists, a hypothetical ligand-based pharmacophore model was built, and a new class of potent TGR5 agonists, based on the novel 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazole core, was discovered by rational design. Three distinct synthetic methods for constructing 4,5-dihydro-1,2,4-oxadiazoles and extensive structure-activity relationship studies are reported herein. Compound (R)-54n, the structure of which was determined by single-crystal X-ray diffraction and quantum chemical solid-state TDDFT-ECD calculations, showed the best potency, with an EC50 value of 1.4nM toward hTGR5. Its favorable properties invitro warrant further investigation.