22610-99-7

Usage

Uses

Used in Pharmaceutical Industry:
CIS-DIETHYLSTILBESTROL is used as a synthetic estrogen for hormone replacement therapy and treatment of certain conditions related to estrogen deficiency. Its application in this industry is due to its ability to mimic the effects of natural estrogen, providing relief and treatment for various health issues.
Used in Research and Development:
CIS-DIETHYLSTILBESTROL is used as a research compound for studying the effects of estrogen on the body and its potential applications in medicine. Its role in this industry is to provide a controlled and consistent source of synthetic estrogen for scientific experiments and clinical trials.
Used in Solvent Systems:
CIS-DIETHYLSTILBESTROL is used as a solute in solvents such as DMSO, DMF, and ethanol for various chemical reactions and processes. However,

Upstream product

• 2297-48-5 C₁₈H₂₂O₃ 
• 130-80-3 3,4-bis-(4-propionyloxy-phenyl)-hex-3c-ene 
• 7664-41-7 ammonia 
• 18922-12-8 4,4-Bis(p-acetoxyphenyl)-3-hexanone 
• 18922-13-9 diethylstilbesterol pinacolone 
• 70-70-2 4-hydroxypropiophenone 
• 56-53-1 diethylstilbestrol 
• 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

• 106424-48-0 Diaethylstilboestrol-bis-β-(p-methoxyphenyl)-propionat 
• 106424-56-0 Diaethylstilboestrol-bis-β-(p-propoxyphenyl)-propionat 
• 106990-86-7 Diaethylstilboestrol-bis-β-(p-butoxyphenyl)-propionat 
• 106990-87-8 Diaethylstilboestrol-bis-β-(p-isobutoxyphenyl)-propionat 
• 106301-64-8 Diaethylstilboestrol-bis-β-(p-isopropoxyphenyl)-propionat 
• 107117-00-0 Diaethylstilboestrol-bis-β-(p-hexoxyphenyl)-propionat 
• 106570-08-5 Diaethylstilboestrol-bis-β-(p-heptoxyphenyl)-propionat 
• 107085-21-2 Diaethylstilboestrol-bis-β-(p-decyloxyphenyl)-propionat 
• 107086-56-6 Diaethylstilboestrol-bis-β-(p-dodecyloxyphenyl)-propionat 
• 56-53-1 diethylstilbestrol 
• 88181-17-3 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 

Relevant academic research and scientific papers

NON-ESTROGENIC METABOLITES OF DIETHYLSTILBESTROL PRODUCED BY PROSTAGLANDIN SYNTHASE MEDIATED METABOLISM

Incubation of trans-diethylstilbestrol (E-DES) with prostaglandin synthase (PGS) in vitro leads to the formation of the metabolites cis,cis-dienestrol (Z,Z-DIES) and cis-diethylstilbestrol (Z-DES) which have considerably decreased estrogenic activity compared to their parent compound.Incubations of (14C)-E-DES with PGS in the presence of arachidonic acid (AA) predominantly catalyze formation of the oxidative metabolite Z,Z-DIES, accompanied by the formation of protein bound radioactivity.Inhibition of peroxidative metabolism through addition of indomethacin or absence of AA favors isomerization of E-DES to Z-DES without concomitant formation of protein bound radioactivity.Isomerization is inhibited by phenidone (1-phenyl-3-pyrazolidone).Since PGS activity is present in uterine tissue, these pathways may play a role in the metabolism of DES in its target tissue.

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.

Stereochemistry and Side Products in Reductive Coupling of Alkyl Aryl Ketones to 1,2-Dialkyl-1,2-diarylethylenes

The reductive coupling of alkyl aryl ketones 1 - 3 and 7 - 9 by low valent titanium salts yields predominantly the (Z)-isomers of 11 - 13 and 17 - 19.Evidence is given by 1H NMR spectroscopy.This behavior can be explained by ?-complex formation of phenyl rings with Ti0.Severe steric hindrance, however, favors the (E)-isomers ( -> 14 and 15).Donor groups in p-position, particularly, give increasing amounts of pinacols, 23 - 27, which undergo rearrangement to the ketones 28 and 29.