Molecular structures of 17αβ-acetoxy-3-methoxy-6-oxa-D-homo-8-isoestra-1,3,5(10)-triene and its 4-methyl derivative

Старова, Галина Л.; Selivanov, S. S.; Egorov, M. S.; Селиванов, С. И.; Шавва, А. Г.

doi:10.1134/1.1756642

Cited by 2 publications

(3 citation statements)

References 7 publications

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“…The reaction of the cyclic β-cyanoketone 62 with 6-(3-methoxyphenyl)hex-1-en-3-one (61) gave the decalone cyanohydrin 63, which could be cyclized to D-homosteroids (64,65) …”

Section: Scheme 15mentioning

confidence: 99%

“…61 An NMR study has been performed on the stereo-structure and intramolecular dynamics of D-homoandrostenes and a B-nor-8-iso-D-homoestrone derivative. 62 The crystal structures of two steroid 19,B-dinor-8,10-iso analogs 63 and of two 6-oxa-D-homo-8-isoestra derivatives 64 have been published. An investigation has been made on the phosphorescence of enaminocarbonyl-8-azasteroids (including D-homo derivatives).…”

Section: Figurementioning

confidence: 99%

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Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Wölfling¹

2007

ChemInform

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Both naturally occurring and synthetic D-homologs of compounds with a sterane skeleton exhibit diverse biological activity. The main sources of isolation are plants and marine organisms. The synthetic D-homosteroids are potential leads for drug discovery. This review focuses on steroids with a six-membered carbocyclic ring D and related compounds, the isolation or syntheses of which were reported between the mid-1990s and mid-2006.

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“…The reaction of the cyclic β-cyanoketone 62 with 6-(3-methoxyphenyl)hex-1-en-3-one (61) gave the decalone cyanohydrin 63, which could be cyclized to D-homosteroids (64,65) …”

Section: Scheme 15mentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Wölfling¹

2007

ChemInform

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“…An X-ray crystallographic analysis of compounds 1 and 2 was carried out in [25] and of compound 3 in [26]. We undertook an X-ray crystallographic analysis of compound 4a, the hydrogen atoms of which were located at the calculated positions (Fig.…”

mentioning

confidence: 99%

Molecular structures of some D-homo-6-oxa-8α analogs of steroidal estrogens

Шавва

Старова

Селиванов

et al. 2008

Chem Heterocycl Comp

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By X-ray crystallographic analysis and NMR spectroscopy it was demonstrated that the conformations of several D-homo-6-oxa-8α analogs of steroidal estrogens are similar in the crystal and in solution. The distances between the hydrogen atoms in these molecules, calculated by the ab initio and MM + methods, correspond to the experimental data.At the present time intensive searches are being made for specific inhibitors of the enzymes responsible for the metabolism of steroidal hormones [1][2][3][4][5][6][7]. Such inhibitors are needed for the treatment of various illnesses caused both by imbalance in the hormone content of the organism and by oncological factors. An important condition for the selection of new steroids for detailed investigation is the absence of hormonal activity.Steroid-like compounds bonded covalently to other types of biologically active substances could be used to transport the latter into the target organs and, in the case of peptidylsteroids, to protect them against destruction by the action of proteases [8-10]. The D-homo-6-oxa-8α analogs of steroidal estrogens 1-4 are promising for the synthesis of compounds with such properties [11,12]. O OAc R R O Me H H H O O O R H H H 1 2 1-3 4a,b 1 R 1 = R 2 = H; 2 R 1 = H, R 2 = Me; 3 R 1 = Me, R 2 = H; 4 a R = Me, b R = HThe biological activity of estrogen receptor modulators is determined to a significant degree by the structure of their complexes with the hormone receptors [13][14][15]. Ever greater attention is therefore being paid to the analysis of such complexes aimed at revealing criteria that make it possible to evaluate the biological characteristics of new ligands mediated by a given receptor during the planned selection of new substances for synthesis [16].

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Molecular structures of 17αβ-acetoxy-3-methoxy-6-oxa-D-homo-8-isoestra-1,3,5(10)-triene and its 4-methyl derivative

Cited by 2 publications

References 7 publications

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Recent Developments in the Isolation and Synthesis of D‐Homosteroids and Related Compounds

Molecular structures of some D-homo-6-oxa-8α analogs of steroidal estrogens

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