Investigations on the influence of terminal groups at the C2-propyl side chain of 1,1-bis(4-hydroxyphenyl)-2-phenylpent-1-ene and 1,1,2-tris(4-hydroxyphenyl)pent-1-ene on the estrogen receptor binding and the estrogenic/anti-estrogenic properties

Investigations on the Effects of Basic Side Chains on the Hormonal Profile of (4R,5S)/(4S,5R)-4,5-Bis(4-hydroxyphenyl)-2-imidazolines

“…The 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene showed nearly the same effects on the MCF-7-2a cell line as 4-OHT. Reduction or elongation of the C2-alkyl chain and hydrophilic terminal groups decreased the activity. − Therefore, it can be assumed that high antagonistic properties demand van der Waals contacts to hydrophobic amino acids located around the ethyl chain in the LBD/4-OHT conjugate.…”

Synthesis and evaluation of 2-halogenated-1,1-bis(4-hydroxyphenyl)-2-(3-hydroxyphenyl)-ethylenes as potential estrogen receptor-targeted radiodiagnostic and radiotherapeutic agents

“…Initial studies with radio-iodinated 69 derivatives of steroidal and nonsteroidal estrogen receptor ligands 70 have demonstrated this effect in estrogen receptor-containing cells 71 but not in cells deficient in the estrogen receptor protein [22][23][24][25][26][27][28][29][30]. 72 Although many high affinity estrogen receptor-targeted ligands 73 have been prepared and evaluated, relatively few are structurally 74 amenable to labeling with radiohalogens. Within both the steroidal 75 and nonsteroidal classes of estrogens, introduction of iodine on the 76 phenolic ring results in a substantial reduction of binding affinity 77 as well as increased binding to nontarget proteins [31][32][33][34] In parallel to our work on steroidal estrogens, we also under- 88 took the evaluation of radiohalogenated nonsteroidal estrogens 89 [23, [39][40][41][42][43] (Fig.…”