6898-97-1

Usage

Uses

Used in Analytical Chemistry:
Diethylstilbestrol is used as an internal standard for the analysis of drug residues in the urine of rats and calves. This application takes advantage of its chemical properties to ensure accurate and reliable results in on-line high-performance liquid chromatography (HPLC) with ultraviolet and continuous-flow fast atom bombardment mass spectrometry detectors.
Used in Pharmaceutical Research:
Due to its potent estrogenic activity, Diethylstilbestrol has been a subject of interest in pharmaceutical research. The mechanisms of its isomerization processes and the evaluation of estrogen activity of its cisand trans-forms contribute to the understanding of its effects and potential applications in medicine.

Synthesis

Diethylstilbestrol, trans-α,β-diethyl-4,4
-stilbendiol (28.1.34), is proposed to be synthesized in various ways. According to one of them, desoxyansoine is alkylated by ethyl iodide in the presence of sodium ethoxide, and the resulting ketone (28.1.30) is reacted in a Grignard reaction with ethylmagnesium bromide, which forms the carbinol (28.1.31). Dehydration of Diethylstilbestrol by distillation in the presence of p-toluenesulfonic acid gives dimethyl ether of stilbestrol (28.1.32), methyl groups of which are removed by heating it at high temperatures with potassium hydroxide, thus forming diethylstilbestrol (28.1.33).

InChI:InChI=1/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17-

Upstream product

• 70-70-2 4-hydroxypropiophenone 
• 121-97-1 4-Methoxypropiophenone 
• 4646-94-0 2-(4-methoxyphenyl)-n-butanoic acid 
• 4390-94-7 1,2-bis(4-methoxyphenyl)butanone 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 752225-73-3 C₂₀H₂₄O₂ 
• 7773-34-4 diethylstilbestrol dimethyl ether 

Downstream Products

• 88181-17-3 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 
• 13425-53-1 C₁₈H₂₂O₈P₂ 
• 88181-16-2 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 
• 107086-56-6 Diaethylstilboestrol-bis-β-(p-dodecyloxyphenyl)-propionat 
• 107085-21-2 Diaethylstilboestrol-bis-β-(p-decyloxyphenyl)-propionat 
• 106570-08-5 Diaethylstilboestrol-bis-β-(p-heptoxyphenyl)-propionat 
• 107117-00-0 Diaethylstilboestrol-bis-β-(p-hexoxyphenyl)-propionat 
• 106301-64-8 Diaethylstilboestrol-bis-β-(p-isopropoxyphenyl)-propionat 
• 106990-87-8 Diaethylstilboestrol-bis-β-(p-isobutoxyphenyl)-propionat 
• 106990-86-7 Diaethylstilboestrol-bis-β-(p-butoxyphenyl)-propionat 
• 106424-56-0 Diaethylstilboestrol-bis-β-(p-propoxyphenyl)-propionat 

Relevant academic research and scientific papers

Anti-proliferative activities of flavone-estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl4/Zn-catalysed McMurry cross-coupling reactions

We described the synthesis of flavone-estradiol adducts and indanophen based tamoxifen analogs using a novel SnCl4-Zn reagent via a McMurry cross-coupling reaction and their anti-proliferative evaluation against human cervical cancer cell lines (HeLa) and human breast cancer cell lines (MCF-7 and MDA-MB-231). A library of 32 tamoxifen analogs was synthesized using indanone and propiophenone derivatives and evaluated for anti-proliferative activities. Among them, compounds 3ac, 3ad, 3ae and 3ao exhibited better anti-proliferative potencies (IC50 2.13-3.81 μM) than the drug doxorubicin (IC50 50 2.85 ± 0.17 μM and 2.42 ± 0.23 μM; 3.64 ± 0.28 μM and 2.93 ± 0.14 μM) against breast cancer cells (MCF-7 and MDA-MB-231) respectively and IC50 2.17 ± 0.18 μM and 2.56 ± 0.32 μM against cervical cancer cells (HeLa) respectively than the standard drug. However, compounds 6ac, 6ae, 6af and 6ag showed moderate activity (IC50 10 μM). The structure-activity relationship analysis revealed that the optimal combination of side chains at the para-position of propiophenone and fluoro substituent on the indanone moiety enhanced the anti-proliferative activities of tamoxifen analogs.

Synthesis and biological evaluation of stilbene-based pure estrogen antagonists

The nonsteroidal estrogen diethylstilbestrol can be converted into potent antiestrogens devoid of agonist activity by introduction of side chains with appropriate functional groups. Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists.

Human insulin analogues

The present invention relates to novel human insulin analogues exhibiting a low ability to associate in solution, a method for the preparation of such insulin analogues, insulin preparations containing the human insulin analogues of the invention and a method of treating Diabetes Mellitus using these human insulin analogues.

STERICALLY-DRIVEN ANHYDRIDE FORMATION

Oxidative coupling of highly substituted carboxylic acid dianions affords hindered succinic acid derivatives which undergo facile intramolecular anhydride formation.A novel, but low yield, synthetic sequence converts 4'-methoxypropiophenone into diethylstilbestrol.