448956-67-0

Upstream product

• 448956-66-9 3-(allyloxy)-4-bromophenyl 4-methylbenzenesulfonate 
• 31928-96-8 3-(2-Propenoxy)cyclohex-2-en-1-one 

Downstream Products

• 448956-68-1 4-[3-(allyloxy)-4-bromophenoxy]benzaldehyde 
• 448957-20-8 ethyl (2-bromo-5-(4-(((2,4-difluorobenzyl)(2-methyl-3-((methylsulfonyl)amino)phenyl)amino)methyl)phenoxy)phenoxy)acetate 
• 448957-19-5 ethyl (2-bromo-5-(4-(((2,4-difluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)phenoxy)acetate 
• 448957-18-4 2-bromo-5-(4-{[(2,4-difluoro-benzyl)-(2-methyl-3-nitro-phenyl)-amino]-methyl}-phenoxy)-phenol 

Relevant academic research and scientific papers

Practical regioselective halogenation of vinylogous esters: Synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols

A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology to access polyhaloresorcinols is also reported. These methods create useful functionalized building blocks for further synthetic applications.

Regiodivergent halogenation of vinylogous esters: One-pot, transition-metal-free access to differentiated haloresorcinols

We report an efficient method for the regiodivergent synthesis of halogenated resorcinol derivatives using readily available vinylogous esters and sulfonyl halide halogen donors. Either the 4- or 6-haloresorcinol isomer is accessible from a common precursor. In contrast to conventional oxidants for arene halogenation, mild sulfonyl halides allow broad functional group compatibility. The strategy inherently differentiates the two resorcinol oxygen atoms and enhances the potential for complex molecule synthesis.

Antidiabetic activity of passive nonsteroidal glucocorticoid receptor modulators

Much has been learned about the consequences of glucocorticoid receptor antagonism by studying steroidal active antagonists such as RU-38486 (1). In the liver glucocorticoid receptor antagonism suppresses hepatic glucose production decreasing plasma glucose levels; however, extrahepatic antagonism produces several undesirable side effects including activation of the hypothalamic pituitary adrenal axis. A series of nonsteroidal passive N-(3-dibenzylamino-2- alkyl-phenyl)-methanesulfonamide glucocorticoid receptor modulators was discovered. Liver selective and systemically available members of this series were found and characterized in diabetes and side effect rodent models. A highly liver selective member of this series, acid 14, shows efficacy in the ob/ob model of diabetes. It lowers plasma glucose, cholesterol, and free fatty acid concentrations and reduces the rate of body weight gain. The structurally related systemically available passive modulator 12 lowers glucose, HbA 1c, triglyceride, free fatty acid, and cholesterol levels. Interestingly, it did not acutely activate the hypothalamic pituitary adrenal axis in unstressed CD-1 mice or have the abortive effects observed with 1. These results indicate that passive GR antagonists may have utility as antidiabetic agents.

GLUCOCORTICOID RECEPTOR MODULATORS

Compounds of formula (I) or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.