It was shown that carrying out the reaction of cholesterol photosensitized oxidation in the presence of porphyrins immobilized on the hydrolyzed copolymer of tetrafluorethylene and H + form of perfluoro-3,6-dioxo-5-methyl-6-sulfonylfluorideoctene-1 leads to the formation of not previously described new products: 6β-phormyl-B-norcholestan-3β,5β-diol, 6β-chlorocholestan-3β,5α-diol, cholestan-3β,5α,6β-triol, and 5α-chlorocholestan-3β,6β-diol.

Five new 1,4-dihydropyridines containing 3-dialkylamino-2,2-dimethylpropyl fragments were synthesized. The hypotensive activity of the resulting compounds was studied.

An 11α-nitroxy group was introduced into 17α-ethynylestradiol-3,17-diacetate using a synthetic scheme involving oxidative nitration by cerium ammonium nitrate and configuration inversion at C11 by sodium-borohydride reduction of the 11-nitrate 9α,11β-dihydroxy derivative of the starting steroid. The 11α-nitroxy-containing ethynylestradiol exhibits antiestrogen activity.

ESI MS studies showed that the major collision-activated fragmentation pathway of the [M + Na]+ ions of the title estranes involves elimination of NaCl and HCl molecules. Fragmentation of the [M + H]+ ions involves the functional groups, which provides information on their structures. The fragmentation of the [M + Na]+ and [M + H]+ ions was estimated by quantum-chemical calculations.

Collision-induced fragmentation of the [M + Na]+ and [M + H]+ ions generated from 3-[4- bis-N,N-(2-chloroethyl)aminophenyl]-acetates in the estrane series under electrospray/ionization was studied. Some regularities in fragmentation pathways depending on the nature of functional groups were established. Formation of the [(M + Na) – NaCl]+ ions along with [(M + Na) – HCl]+ ions from the [M + Na]+ ions was explained using quantum chemical calculations for some simplified models.

11-Nitrates of 9α,11β-dihydroxy derivatives of estrone, estradiol, and ethinylestradiol were synthesized by oxidative nitration of the corresponding estratriene 3-acetates with cerium ammonium nitrate. Three methods are given for this reaction. Compounds had high antifertility and estrogen activity. Antifertility actions were much greater than their estrogen activities, as compared with the similar levels seen with ethinylestradiol.

A series of steroids with bis-(2-chlorethyl)amino-containing substituents at position 3 were synthesized on the basis of 11_-hydroxyestra-1,3,5(10)-trienes obtained via a new reaction pathway. All the steroids possess antitumor activity, the most effective ones combining cytotoxic action and antiestrogen activity.

The hormonal compound with the highest cytostatic activity against MCF-7 tumor cells (human breast cancer, BC) and the lowest activity against normal cells (rat skin fibroblasts) was sought among gestagens, androstenes, and antiestrogencytostatics. It was found that antiestrogencytostatics and androstenes had the highest cytostatic activity against tumor cells whereas gestagens and antiestrogencytostatics were least active against fibroblasts. Studies of the activity of the hormonal compounds in combination with doxorubicin on the viability of MCF-7 and rat skin fibroblasts found that all investigated compounds with the exception of dehydroepiandrosterone (DHEA) intensify the cytostatic activity of doxorubicin against tumor cells, the greatest effect seen for antiestrogencytostatics. A chemoprotective effect of androstenes on normal cells was noted.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

The fragmentation of [M+Na](+) ions produced from steroid 11beta-nitrates during electrospray/ionization (ESI) was studied by using ion trap MS/MS technique. The [M+Na](+) ions eliminate NO(2) and HNO(3) for epimers bearing 9beta and 9alpha substituents, respectively. As the main fragmentation pathways are determined mainly by the configuration at C-9 and alternative fragmentation does not practically occur, this offers the possibility for the determination of the configuration at chiral C-9 centre in the estrane 11beta-nitrate series by ESI mass spectrometry.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Esterification of 3-hydroxyl group in 11α-acyloxyestra-1,3,5(10)-trienes with p -[bis(2-chloroethyl)amino]phenyl acetic acid led to antitumor steroids displaying antiestrogenic and cytotoxic activities. Our substances exhibit their activities on the model of murine mammary adenocarcinoma Ca-755, with inhibition of the tumor growth being 94–99%. A new approach was used to the 11α-hydroxylation of estra-1,3,5(10)-trienes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

AbstractFor Abstract see ChemInform Abstract in Full Text.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.