250279-13-1

Basic information

• Product Name: 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene
• Synonyms: 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene
• CAS NO: 250279-13-1
• Molecular Weight: 316.423
• Mol File: 250279-13-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene(250279-13-1)
• EPA Substance Registry System: 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene(250279-13-1)

Safety Data

• Hazardous Substances Data: 250279-13-1(Hazardous Substances Data)

Upstream product

• 7342-82-7 3-Bromothianaphthene 
• 3375-31-3 palladium diacetate 
• 156642-03-4 4'-methoxy-biphenyl-4-boronic acid 
• 100-68-5 methyl-phenyl-thioether 
• 67132-14-3 4′-methoxy-[1,1′-biphenyl]-4-carbonyl chloride 

Downstream Products

• 250342-62-2 (4-fluoro-phenyl)-[3-(4'-methoxy-biphenyl-4-yl)-benzo[b]thiophen-2-yl]-methanol 
• 473713-49-4 N-{3-[4'-(2-benzyl-benzo[b]thiophen-3-yl)-3,5-dibromo-biphenyl-4-yloxy]-3-methoxycarbonyl-propyl}-phthalamic acid 
• 1027525-63-8 C₄₄H₃₆O₅S 
• 1025890-27-0 2-[4-(2-benzyl-benzo[b]thiophen-3-yl)-4''-methoxy-[1,1';3',1'']terphenyl-4'-yloxy]-3-phenyl-propionic acid methyl ester 
• 1027599-25-2 2-[4-(2-benzyl-benzo[b]thiophen-3-yl)-4''-chloro-[1,1';3',1'']terphenyl-4'-yloxy]-3-phenyl-propionic acid methyl ester 
• 1026732-77-3 [4-(2-benzyl-benzo[b]thiophen-3-yl)-3'',4'',5''-trimethoxy-[1,1';3',1'']terphenyl-4'-yloxy]-acetic acid methyl ester 
• 1027229-85-1 [4-(2-benzyl-benzo[b]thiophen-3-yl)-5'-bromo-2'',4''-dimethoxy-[1,1';3',1'']terphenyl-4'-yloxy]-acetic acid methyl ester 
• 250342-08-6 (2R) 2-{4'-[2-(2,2-dimethyl-benzo[1,3]dioxol-5-ylmethyl)-benzo[b]thiophene-3-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid 
• 1027191-74-7 2-[4'-(2-benzyl-benzo[b]thiophen-3-yl)-3,5-dibromo-biphenyl-4-yloxy]-4-phenyl-butyric acid methyl ester 
• 1026607-16-8 2-{4'-[2-(2,4-dihydroxy-benzyl)-benzo[b]thiophen-3-yl]-biphenyl-4-yloxy}-3-phenyl-propionic acid methyl ester 
• 1026583-11-8 2-{4'-[2-(2,2-dimethyl-benzo[1,3]dioxol-5-ylmethyl)-benzo[b]thiophen-3-yl]-biphenyl-4-yloxy}-3-phenyl-propionic acid methyl ester 

Relevant articles and documents

BIPHENYL SULFONYL ARYL CARBOXYLIC ACIDS USEFUL IN THE TREATMENT OF INSULIN RESISTANCE AND HYPERGLYCEMIA

This invention provides compounds of Formula (I) having the structure wherein A is (a) or (b), Q is (c) or (d); B is carbon or nitrogen; D is oxygen, sulfur, or nitrogen; E is carbon or nitrogen; X is carbon, nitrogen, oxygen, or sulfur; Y is a bond, meth

Biphenyl sulfonyl aryl carboxylic acids useful in the treatment of insulin resistance and hyperglycemia

This invention provides compounds of Formula I having the structure wherein A, Q, R3, and R4 are as defined hereinbefore in the specification, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties

Insulin resistance in the liver and peripheral tissues, together with a pancreatic cell defect, are the common causes of Type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibition of PTPases may be an effective method in the treatment of Type 2 diabetes. We have identified two novel series of benzofuran/benzothiophene biphenyl oxo-acetic acids and sulfonyl- salicylic acids as potent inhibitors of PTP1B with good oral antihyperglycemic activity. To assist in the design of these inhibitors, crystallographic studies have attempted to identify enzyme inhibitor interactions. Resolution of crystal complexes has suggested that the inhibitors bind to the enzyme active site and are held in place through hydrogen bonding and van der Waals interactions formed within two hydrophobic pockets. In the oxo-acetic acid series, hydrophobic substitutents at position-2 of the benzofuran/benzothiophene biphenyl framework interacted with Phe182 of the catalytic site and were very critical to the intrinsic activity of the molecule. The hydrophobic region of the catalytic-site pocket was exploited and taken advantage by hydrophobic substituents at either the α-carbon or the ortho aromatic positions of the oxo-acetic acid moiety. Similar ortho aromatic substitutions on the salicylic acid-type inhibitors had no effect, primarily due to the different orientation of these inhibitors in the catalytic site. The most active inhibitors of both series inhibited recombinant human PTP1B with phosphotyrosyl dodecapeptide TRDI(P)YETD(P)Y(P)YRK as the source of the substrate with IC50 values in the range of 20-50 nM. Compound 68 was one of the most active compounds in vivo, normalizing plasma glucose levels at the 25 mg/kg dose (po) and the 1 mg/kg dose (ip). Compound 68 was also selective against several other PTPases.