Trans-diethylstilbestrol

Liquid paraffin — triethanolamine cis/trans- diethylstilbestrol, ethynylestradiol 3-fold chloroform—liqmd paraffin — triethanolamine (60 -1-10 -1-10) [257]... 

Fig. 1 Fluorescence scan of a blank (A) and of a diethylstilbestrol-ethinylestradiol mixture (B), each with 10 ng substance per chromatogram zone. Start (1), cis-diethylstilbestrol (2), trans-diethylstilbestrol (3) ethonsylestradiol (4), front (5).

Another early achievement (Fig. 1.2) was the synthesis and the pharmacological evaluation of trans-diethylstilbestrol as an estrogenic agent showing similarities with estradiol [21]. Here again the proposed model was two-dimensional [22], despite the fact that the non-planar conformation of estradiol was already known. 

DIETHYL-(E)-4,4 -STILBENEDIOL a,a -DIETHYL-4,4 -STILBENEDIOL trans-a,a -DIETHYL-4,4 -STIEBENEDI-OL 2,2 -DIETHYL-4,4 -STILBENEDIOL trans-DIETHYLSTILBESTEROL DIETHYLSTILBESTROL trans-DIETHYLSTILBESTROL DIETHYLSTILBO-ESTEROL ttans-DIETHYLSTILBOESTEROL DIETILESTILBESTROL (SPANISH) 4,4 -DIHYDROXY-DIETHYLSTILBENE 4,4 -DIHYDROXY-a,p-DIETHYL-STILBENE 3,4 (4,4 -DIHYDROXYPHENYL)HEX-3-ENE... 

DIETHYLSTILBESTROL see DKA600 trans-DIETHYLSTILBESTROL see DKA600 DIETHYLSTILBESTROL DIPROPIONATE see DKBOOO... 

Simultaneous trans-diethylstilbestrol, 17a-methyltestosterone, nandrolone, 17p-trenbo-... 

When stilboestrol (diethylstilbestrol, 62) was photolysed in aqueous methanol at 254 nm it gave the stable 4a,4b-dihydrophenanthrene dione (63). The mechanism required a photo trans-cis isomerization, photocyclization and spontaneous enol-keto tautomerism [53,54]. Previous workers had carried out a similar irradiation in dilute acetic acid and obtained the expected aromatic product (64) [55],... 

Diethylstilbestrol is a derivative of stilbene, and it differs from sin-estrol by the presence of a double bond with trans-configuration of the two phenyl groups. In terms of estrogenic activity, this drug surpasses both estrone and hexestrol. Synonyms of this drug are distil-ben, menopax, stilphostrol, tilosteron, antigestil, and many others. 

Winkler VW, Nyman MA, Egan RS (1971) Diethylstilbestrol cis-trans isomerization and estrogen activity of diethylstilbestrol isomers. Steroids 17 197-207... 

DIETHYLSTILBESTROL PROPIONATE see DKBOOO DIETHYLSTILBOESTEROL see DKA600 trans-DIETHYLSTlLBOESTEROL see DKA600 DIETHYL SUCCINATE (FCC) see SNBOOO DIETHYL SULFATE see DKBllO DIETHYLSULFID (CZECH) see EPHOOO DIETHYL SULFIDE (DOT) see EPHOOO DIETHYL SULFIDE-2,2 -DICARBOXYLIC ACID see BHMOOO... 

The initial photochemical step, (211) to (212), can be most simply viewed as a perturbed 6e electrocy-clic process, suggesting a trans configuration via conrotation for Ae dihydrophenanthrene intermediate (212). In support of this hypothesis, the stabilization of (216) by tautomerism to (217) in the photolysis of diethylstilbestrol (214), followed by ozonolysis, afforded only the racemic form of 1,2,3,4-buta-netetracarboxylic acid (218). The majority of dihydrophenanthrenes, however, are thermally unstable and undergo conversion to phenanthrenes (under oxidative or non-oxidadve conditions) or 1,/-H shifts to isomeric 9,10-dihydrophenanthrenes. ... 

FIGURE 16.13 Partial scheme for the metabolism of diethylstilbestrol (DES). DES is administered as the trans isomer (E-DES), which, in solution, is in equilibrium with the cis isomer (Z-DES). Cytochrome P450 enzymes oxidize E-DES and Z-DES to a postulated chemically reactive semiquinone (1), which is further oxidized to a quinone (2), thereby generating reactive oxygen species (ROS) that oxidize cellular macromolecules. Redox cycling is perpetuated and ROS formation is amplified by two enzymes, cytochrome P450 or cytochrome bs reductase, which reduce the quinone back to the semiquinone. The unstable semiquinone and diol epoxide (3) metabolites are presumably those that bind to DNA to form adducts and initiate carcinogenesis. 

The steroid nucleus is not required for estrogenic action. Several derivatives of stilbene (diphenylethylene) that were used therapeutically demonstrate potent estrogenic activity. Diethylstilbestrol (DES), prepared in 1939, was one of these stilbenes (Fig. 46.8). A trans stilbene, DES has 10-fold the estrogenic potency of its cis isomer, largely because the trans isomer more closely resembles estradiol (20). Unfortunately, when DES was administered to relieve pregnancy-related symptoms, it was correlated with abnormal growth in the offspring. 

Fregert S, Rorsman H (1962) Hypersensitivity to diethylstilbestrol with cross sensitization to benzestrol. Acta Derm Venereol (Stockh) 42 290-293 Fregert S, Hjorth N, Magnusson B et al. (1969) Epidemiology of contact dermatitis. Trans St John s Hosp Dermatol Soc 55 17-35... 

Supported liquid membranes (SLMs) consisting of 5% tri-n-octylphosphine oxide (TOPO) dissolved in di-w-hexylether/n-undecane (1 1) have been used in the simultaneous extraction of a mixture of three stUbene compounds (dienestrol, diethylstilbestrol, and hexestrol) in cow s milk, urine, bovine kidney, and liver tissue matrices [183]. The efficiencies obtained after the enrichment of 1 ng/1 stilbenes in a variety of biological matrices of milk, urine, liver, kidney, and water were 60-70, 71-86, 69-80, 63-74, and 72-93%, respectively. A new method to contribute to the discrimination of polyphenols including resveratrol with synthetic pores was proposed [184]. The work [185] evaluated two types of commonly available chiral detectors for their possible use in chiral method development and screening polarimeters and CD detectors. Linearity, precision, and the limit of detection (LOD) of six compounds (trans-stilbene oxide, ethyl chrysanthemate, propranolol, 1-methyl-2-tetralone, naproxen, and methyl methionine) on four common detectors (three polarimeters and one CD detector) were experimentally determined and the limit of quantitation calculated from the experimental LOD. trans-Stilbene oxide worked well across all the detectors, showing good linearity, precision, and low detection limits. However, the other five compounds proved to be more discriminating and showed that the CD detector performed better as a detector for chiral screens than the polarimeters. 

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