Design and synthesis of novel benzothiophene analogs as selective estrogen receptor covalent antagonists against breast cancer was written by Bai, Chengfeng;Ren, Shengnan;Wu, Shuangjie;Zhu, Meiqi;Luo, Guoshun;Xiang, Hua. And the article was included in European Journal of Medicinal Chemistry in 2021.COA of Formula: C13H12O2 The following contents are mentioned in the article:
Endocrine therapy (ET) has benefited patients with estrogen receptor alpha (ERα) pos. breast cancer for decades. Selective estrogen receptor modulator (SERM) such as Tamoxifen represents the clin. standard of care (SoC). Despite the therapeutic importance of current SoC agents, 30-50% of prolonged treatment patients inevitably generated resistant tumor cells, usually eventually suffered tumor relapse and developed into metastatic breast cancer (MBC), which was the leading cause of female cancer-related mortality. Among these, most resistant tumors remained dependent on ERα signaling, which reignited the need for the next generation of ERα related agents. Authors hypothesized that selective estrogen receptor covalent antagonists targeting ERα would provide a therapeutic alternative. In the current work, series of novel benzothiophene hybrids I (R1 = H, Me; R2 = Me; R1R2 = (CH2)3, (CH2)5, etc.) II, III (R3 = R4 = H, Me) and IV bearing electrophile moieties were synthesized and biol. evaluated. The representative analog I (R1R2 = (CH2)3) exhibited potent anti-proliferative effect in MCF-7 cell lines in vitro, and further mechanism studies confirmed the necessity of covalent bonding. More importantly, I could attenuate the expression of TFF-1, GREB-1 and down-regulate the levels of cellular ERα protein. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2COA of Formula: C13H12O2).
4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.COA of Formula: C13H12O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem