571-92-6Relevant academic research and scientific papers
Synthesis method of 6-ketoestradiol
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Paragraph 0030-0031, (2020/01/25)
The invention belongs to the technical field of preparation of steroid hormone intermediate, and particularly relates to a synthesis method of 6-ketoestradiol. According to the synthesis method, a compound 1 is taken as a raw material to obtain the 6-ketoestradiol through the following reaction route (please see the specifications for the reaction route). Different from estrone, the raw materialsin the synthesis method are low in price, wide in source and low in cost. By optimizing the reaction route, when 6-site carbanyl groups are introduced, the 6 site is the only active site, selectivityof oxidation is greatly improved, and the reaction condition is also environmentally friendly. The brand-new synthesis route of the 6-ketoestradiol is provided, the technological condition is mild, environment friendliness is achieved, and the synthesis method is suitable for industrial production.
Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water
Zhao, Lei-Min,Meng, Qing-Yuan,Fan, Xiang-Bing,Ye, Chen,Li, Xu-Bing,Chen, Bin,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 3020 - 3024 (2017/03/13)
Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C?H bond of the alcohol (R1CH(OH)R2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.
PROCESS FOR THE PREPARATION OF FULVESTRANT
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Paragraph 0046, (2015/11/16)
The present invention relates to an improved process for the preparation of Fulvestrant (I). Also, provided is novel intermediate of Fulvestrant and a process for the preparation of the same.
PROCESS FOR PREPARING 7-ALPHA-[9-(4,4,5,5,5-PENTAFLUOROTHIOPENTYL) NONYL]ESTRA-1,3,5(10)-TRIENE-3,17-BETA-DIOL
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Paragraph 0044; 0045; 0046; 0047; 0048, (2014/09/02)
A process is described for the industrial scale preparation of 7a-[9-(4,4,5,5,5- 5 pentafluorothiopentyI)nonyl]estra-1,3,5(10)-triene-3,17?-diol, a precursor of steroids with hormonal activity which include Fulvestrant.
Synthesis, anti-oxidant activity, and cytotoxicity of salicyloyl derivatives of estra-1, 3, 5(10)-triene and androst-5-ene
Gasi, Katarina Penov,Djurendic, Evgenija,Dojcinovic-Vujaskovic, Sanja,Gakovic, Andrea,Jovanovic-Santa, Suzana,Kojic, Vesna,Sakac, Marija
experimental part, p. 284 - 294 (2012/08/28)
Since many estrane and androstane derivatives exhibit cytotoxic, anti-oxidant, or anti-hormone activity, new steroidal derivatives were synthesised from appropriate estrogen or androgen precursors in order to obtain potential therapeutics for the treatment of steroid-dependent diseases. Starting from estradiol (I ), 6-oxo derivatives V and VII were prepared. 17β-Salicyloyl-6-oxo derivatives VI and VIII were synthesised by the reaction of compounds V or VII with methyl salicylate in the presence of sodium. 17β-Salicyloyloxy estradiol IX was prepared from estradiol. Beckmann fragmentation of 16-oxyimino alcohols XII and XIII with methyl salicylate yielded corresponding Dseco derivatives XIV and XV. Simultaneous fragmentation and acylation of compound XII resulted in 3β-salicyloyl-D-seco derivative XVI which was also obtained from compound XIV. Anti-oxidant assays of the newly synthesised compounds V-IX, XIV, and XVI indicated a stronger capacity for hydroxyl radical scavenging, and a weaker capacity for DPPH radical scavenging, compared with the standard anti-oxidants BHA and BHT. Compounds V, XIV, and XVI showed higher or the same activity as BHT. The cytotoxicity of new compounds was evaluated against human breast and prostate carcinoma cells. Compound VI exhibited strong cytotoxicity against MDA-MB-231 cells; compound XIV exhibited strong cytotoxicity against PC-3 cell line, while compound VII moderately inhibited the growth of PC-3 cells.
Synthesis, anti-oxidant activity, and cytotoxicity of salicyloyl derivatives of estra-1,3,5(10)-triene and androst-5-ene
Ga??i, Katarina,Djurendi??, Evgenija,Doj??inovi??-Vuja??kovi??, Sanja,Gakovi??, Andrea,Jovanovi??-??anta, Suzana,Koji??, Vesna,Saka??, Marija
, p. 284 - 294 (2015/03/05)
Since many estrane and androstane derivatives exhibit cytotoxic, anti-oxidant, or anti-hormone activity, new steroidal derivatives were synthesised from appropriate estrogen or androgen precursors in order to obtain potential therapeutics for the treatment of steroid-dependent diseases. Starting from estradiol (I), 6-oxo derivatives V and VII were prepared. 17?2-Salicyloyl-6-oxo derivatives VI and VIII were synthesised by the reaction of compounds V or VII with methyl salicylate in the presence of sodium. 17?2-Salicyloyloxy estradiol IX was prepared from estradiol. Beckmann fragmentation of 16-oxyimino alcohols XII and XIII with methyl salicylate yielded corresponding D-seco derivatives XIV and XV. Simultaneous fragmentation and acylation of compound XII resulted in 3?2-salicyloyl-D-seco derivative XVI which was also obtained from compound XIV. Anti-oxidant assays of the newly synthesised compounds V-IX, XIV, and XVI indicated a stronger capacity for hydroxyl radical scavenging, and a weaker capacity for DPPH radical scavenging, compared with the standard anti-oxidants BHA and BHT. Compounds V, XIV, and XVI showed higher or the same activity as BHT. The cytotoxicity of new compounds was evaluated against human breast and prostate carcinoma cells. Compound VI exhibited strong cytotoxicity against MDA-MB-231 cells; compound XIV exhibited strong cytotoxicity against PC-3 cell line, while compound VII moderately inhibited the growth of PC-3 cells.
Design, synthesis, and estrogenic activity of a novel estrogen receptor modulator - A hybrid structure of 17β-estradiol and vitamin E in hippocampal neurons
Zhao, Liqin,Jin, Chunyang,Mao, Zisu,Gopinathan, Madathil B.,Rehder, Kenneth,Brinton, Roberta D.
, p. 4471 - 4481 (2008/03/12)
We recently discovered that ICI 182,780 (1), an antagonist of estrogen receptor (ER)-dependent proliferation in reproductive tissues, functions as an estrogenic agonist in primary neurons. The present study investigated whether the agonist properties of 1 in neurons could be translated into structural analogs. 7α-[(4R,8R)-4,8,-12-trimethyltridecyl]estra-1,3,5-trien-3, 17β-diol (2), a hybrid structure of 17β-estradiol and vitamin E, was synthesized and found to bind to both ERα and ERβ. In vitro analyses demonstrated that 2 was neuroprotective and effective in activating molecular mechanisms associated with estrogenic agonist activity in rat primary hippocampal neurons. Collectively, the data support an estrogenic agonist profile of 2 action comparable to 1 in primary neurons, confirming that estrogenic activity of 1 in neurons is not a unique phenomenon. These results provide support for the development of a brain-selective ER modulator, with potential as an efficacious and safe estrogen alternative to prevent Alzheimer's disease and cognitive decline in postmenopausal women.
First synthesis of a steroid containing an unstable 19-nor-androsta-1,5-dien-3-one system
Cadot, Christine,Poirier, Donald,Philip, Anie
, p. 4384 - 4392 (2007/10/03)
Mechanisms involved in the maintenance of human pregnancy and initiation of labour are poorly defined. A novel steroid hormone named estradienolone (ED), and having an unusual 19-nor-androsta-1,5-dien-3-one system, was previously reported. However, ED is scarcely available from urine, placenta and blood of pregnant women. For this reason, we have synthesized ED in order to verify its proposed structure. Although a 1,5-dien-3-one system had already been described for a C19-steroid (androstane) nucleus (no possible aromatization), the synthesis of the 19-nor-analogue is a major challenge because this system is very sensitive to aromatization. We now describe the successful construction and characterization of this unstable system. Starting from nortestosterone, the synthesis of 17β-hydroxy-19-nor-androsta-1,5-dien-3-one (1) is based on a protection of the 5,6-double bond, the introduction of the second 1,2-double bond, the careful recovery of the exo double bond and a final regioselective oxidation or reduction.
Synthesis of anti-estrogenic and other therapeutic steroids from 21-hydroxy-19-norpregna-4-en-3-one
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, (2008/06/13)
Syntheses of steroids such as 3-hydroxy-7α-methyl-21-[2′-methoxy-4′-(diethylaminomethyl)-phenoxy]-19-norpregna-1,3,5(10)triene citrate (“SR 16234”) and analogs thereof are provided, wherein 21-hydroxy-19-norpregna-4-en-3-one serves as a starting material
Aromatization of 19-Oxygenated Androst-4-ene-3,6,17-triones with Human Placental Microsomes
Numazawa, Mitsuteru,Sugiyama, Takanori,Nagaoka, Masao
, p. 289 - 292 (2007/10/03)
To gain insight into the aromatization sequence of androst-4-ene-3,6,17-trione (1), a suicide substrate of aromatase, the aromatization of its 19-hydroxy and 19-oxo analogs 2 and 3 with human placental microsomes, was studied using GC-MS. Steroids 2 and 3 were separately incubated with the microsomes in the presence of NADPH in air. The GC-MS analysis of the trimethylsilyl derivative of the aromatization product indicated that both the 19-oxygenated steroids 2 and 3 were aromatized to yield 6-oxoestrogens, 6-oxoestrone (4) and 6-oxoestradiol (5), in each experiment. The aromatization rates of substrates 2 and 3 were 605+/-48 and 1794+/-75 pmol/mg protein/10 min, respectively. These relatively higher rates, compared to that of the parent steroid 1 (73.2+/-6.6 pmol/mg protein/10 min), indicates that the suicide substrate 1 is aromatized through the 19-oxygenated intermediates 2 and 3.
