Convenient Synthesis and Structural Characterization of a Series of Methyl 4-[2-(cyclized amino)ethoxy]benzoate Esters as Key Intermediates in Synthesis of Selective Estrogen Receptor Modulators.

摘要

Estrogen receptors, the important selective targets in management of serious aspects in women health challenging issues, guided the scope of drug discovery towards developing new entities treating osteoporosis and breast cancer. Tracing aminoethoxyphenyl pharmacophoric essential antagonistic group, abundantly present in Selective Estrogen Receptors Modulators (SERMs), directed the authors to study and explore the prospect to synthesize and exclusively characterize a series of methyl 4-[2-(cyclized amino)ethoxy] benzoate esters 9a-c rather than their reported free acids as fundamental and convenient key intermediates synthesizing potential SERMs. This paper describes synthesis and spectral characterization of these esters. The relative significant 1H-NMR shifts related to synthesized derivatives were illustrated. 13C-NMR data were particularly discussed. Moreover, molecular ion peaks and different fragmentation patterns in mass spectral analysis were demonstrated. Furthermore, retention time of different derivatives at specified conditions using gas chromatography-mass spectrometry was assigned. Purity of compounds was confirmed by elemental analysis; found data were within ± 0.4% of the theoretical values.