64-82-4Relevant academic research and scientific papers
ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS
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Page/Page column 147-149, (2021/05/21)
The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)
Efficient approach to novel 1α-triazolyl-5α-androstane derivatives as potent antiproliferative agents
Kadar, Zalan,Baji, Adam,Zupko, Istvan,Bartok, Tibor,Woelfling, Janos,Frank, Eva
supporting information; experimental part, p. 8051 - 8057 (2012/01/04)
Stereoselective 1,4-Michael addition of azoimide to 17β-acetoxy- 5α-adrost-1-en-3-one was carried out to furnish a 1α-azido-3-ketone, which was reduced to give the 3β- and 3α-hydroxy epimers in a ratio of 5:2. The Cu(i)-catalyzed 1,3-dipolar cycloaddition of the major isomer to terminal alkynes afforded 1α-triazolyl derivatives, which were deacetylated to the corresponding 3β,17β-diols or oxidized to the analogous 3-ketones. However, the ability of the minor 1α,3α- azidoalcohol to undergo similar cyclization was found to be affected significantly by the steric bulk of the substituents on the alkyne reaction partner. All triazolyl compounds were tested in vitro on three malignant gynecological cell lines (HeLa, MCF7 and A2780). The Royal Society of Chemistry 2011.
An efficient synthesis of 5α-androst-1-ene-3,17-dione
Zhang, Huyue,Qiu, Zhuibai
, p. 1088 - 1090 (2007/10/03)
5α-Androst-1-ene-3,17-dione (5) as a prodrug of 1-testosterone (4) was prepared in four steps from 17β-Acetoxy-5α-androstan-3-one (stanolone acetate) (1) in high yield. Thus, stanolone acetate (1) was brominated in the presence of hydrogen chloride in acetic acid to give 17β-acetoxy-2-bromo-5α-androstan-3-one (2), which underwent dehydrobromination using lithium carbonate as base with lithium bromide as an additive to give 17β-acetoxy-5α-androst-1-en-3-one (3) in almost quantitative yield with 97% of purity. Compound (3) was hydrolyzed with sodium hydroxide to give 17β-hydroxy-5α-androst-1-en-3-one (4,1-testosterone), which was oxidized with chromium trioxide to afford 5α-androst-1-ene-3,17-dione (5). The overall yield of 5 was 78.2% with purity of 99%. In this method, the formation of 4-ene was diminished when 1-ene was introduced, and its mechanism was also discussed.
Synthesis of α,β-unsaturated ketone from α-iodo ketone using photoirradiation
Ji, Shun-Jun,Takahashi, Eiji,Takahashi, T. Tomoyoshi,Horiuchi, C. Akira
, p. 9263 - 9266 (2007/10/03)
Irradiation of α-iodo ketone in hexane under a nitrogen atmosphere with a high-pressure mercury lamp (λ>300nm) at room temperature afforded the corresponding α,β-unsaturated ketones in good yield. This reaction affords a new, clean and convenient synthetic method for the α,β-unsaturated ketone.
α-FLUORINATION OF KETONES BY XENON AND IODOBENZENE DIFLUORIDES: A STEREOCHEMICAL EVIDENCE DEMONSTRATING THEIR MECHANISTIC DIFFERENCES
Tsushima, Tadahiko,Kawada, Kenji,Tsuji, Teruji
, p. 1165 - 1168 (2007/10/02)
Xenon difluoride reacts smoothly with various steroid silyl enol ethers in the absence of any acid catalyst to afford stereoselectively α-oriented α-fluoroketones in good yields while iodotoluene difluoride reacts rather sluggishly with these silyl enol ethers to competitively produce β-oriented α-fluoro ketones, elimination and other nucleophilic substitution products.The observed stereochemical contrast clearly suggest an electrophilic and nucleophilic mechanism for these reactions, respectively.
Michael Additions to Steroidal Enones
Campbell, Malcolm M.,Jigajinni, Veerappa B.,Wightman, Richard H.
, p. 2537 - 2546 (2007/10/02)
Reaction of steroidal 1-en-3-ones with electron-rich arene thiols gives 1α-adducts under base catalysis, whilst with acid catalysis 1α,3-bis-adducts are formed.Interaction of thiourea with 1-en-3-one systems gives a novel bridged ring structure.Various related Michael additions are described, and parameters defined for successful reaction in steroidal enones.Oxidation of the β-arylthio ketones to the sulphoxide leads to spontaneous regeneration of the enone system.
Mechanistic studies in the photochemical fries rearrangement of enol esters
Veierov, Dan,Mazur, Yehuda,Fischer, Ernst
, p. 1659 - 1664 (2007/10/02)
Photolysis of several enol esters produces the corresponding 1,3-Fries products, i.e. the keto forms of the β-diketones, as the sole primary photoproducts. The quantum yields of the rearrangements under a variety of conditions were measured. They decrease when the number of fused aromatic rings in the acyl part of the molecules is increased. The photobehaviour of the 2-anthroyl derivative is exceptional, in being affected both by the exciting wavelength and the solvent. Its irradiation at 254 nm results in a photo-Fries rearrangement (p.f.r.) with a yield twice that in ethanol; irradiation at 366 nm causes only inefficient dimerization. Explanations are forwarded for the general photobehaviour of the enol esters and its relation to the 1,3-p.f.r. of aryl esters and to other photoinduced 1,3-shifts.
