131008-23-6

Basic information

• Product Name: 6,7-DIMETHYL-3,4-DIHYDRO-1H-2-BENZOTHIOPYRAN-4-ON-1-CARBOXYLIC ACID
• Synonyms: 6,7-DIMETHYL-3,4-DIHYDRO-1H-2-BENZOTHIOPYRAN-4-ON-1-CARBOXYLIC ACID
• CAS NO: 131008-23-6
• Molecular Formula: C₁₂H₁₂O₃S
• Molecular Weight: 236.29
• Mol File: 131008-23-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,7-DIMETHYL-3,4-DIHYDRO-1H-2-BENZOTHIOPYRAN-4-ON-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DIMETHYL-3,4-DIHYDRO-1H-2-BENZOTHIOPYRAN-4-ON-1-CARBOXYLIC ACID(131008-23-6)
• EPA Substance Registry System: 6,7-DIMETHYL-3,4-DIHYDRO-1H-2-BENZOTHIOPYRAN-4-ON-1-CARBOXYLIC ACID(131008-23-6)

Safety Data

• Hazardous Substances Data: 131008-23-6(Hazardous Substances Data)

Upstream product

• 131007-91-5 ethyl 6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1carboxylate 
• 79714-32-2 ethyl α-chloro-α-(3,4-dimethylphenyl)acetate 
• 131030-77-8 ethyl 2-(3,4-dimethylphenyl)-2-hydroxyacetate 
• 131031-08-8 carboxymethylsulfanyl-(3,4-dimethyl-phenyl)-acetic acid ethyl ester 

Relevant articles and documents

Optically active 2R, 4S benzothiepin isomer

This invention relates to an optically active benzothiepin derivative represented by the formula: wherein R represents a lower alkyl group; R1and R2independently represent a lower alkyl group, or may bind together to form a ring, which exhibits excellent osteogenesis-promoting action and is useful as a prophylactic or therapeutic drug for bone diseases.

Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation

In a search for therapeutic agents for the treatment of osteoporosis and bone fracture, we found that 2-benzothiopyran-1-carboxamide derivatives 1, derived from ipriflavone as a lead compound, increase cellular alkaline phosphatase activity in cultures of rat bone marrow stromal cells. Further modification of 1 has led to the discovery of more potent 3-benzothiepin-2- carboxamide derivatives 2. Of these, 3-benzothiepin derivatives bearing a 4- (dialkoxyphosphorylmethyl)phenyl group on the 2-carboxamide moiety such as 2h and 2q exhibited significant improvement of activity compared to ipriflavone. Asymmetric synthesis of 2h and 2q revealed that the (-)-isomers possessed activities superior to those of the (+)-isomers. Further evaluation of these compounds using the mouse osteoblastic cell line MC3T3-E1 revealed that (-)- 2q enhanced the effect of bone morphogenetic protein. In addition, application of a sustained-release agent containing 2q increased the area of newly formed bone in a rat skull defect model. Based on these findings, (-)- 2q was selected for further investigation as a new drug stimulating bone formation. Synthesis and structure-activity relationships for this novel series of 2-benzothiopyran and 3-benzothiepin derivatives are detailed.