162210-29-9Relevant articles and documents
Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation
Oda, Tsuneo,Notoya, Kohei,Gotoh, Masayuki,Taketomi, Shigehisa,Fujisawa, Yukio,Makino, Haruhiko,Sohda, Takashi
, p. 751 - 760 (2007/10/03)
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.
Benzopyran derivatives and their use
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, (2008/06/13)
This invention relates to a compound represented by the formula: STR1 wherein B represents a hydrogen atom or a lower alkyl group; ring A represents a benzene ring which may have one or more substituents; ***** represents a single or double bond; Q1 represents the group represented by the formula, STR2 or a hydrocarbon residue substituted with the group represented by the formula, STR3 wherein X represents a bond or a spacer having a chain length of 1 to 4 atoms as the linear moiety which may have one or more side chains; R1 and R2, whether identical or not, independently represent a hydrogen atom or a lower alkyl, or may bind together to form a ring; Q2 represents a hydrogen atom, a hydrocarbon residue which may be substituted or a heterocyclic ring residue which may be substituted; or a salt thereof.