1624-62-0Relevant articles and documents
Estrogen-cis-dichloroethylenediamineplatinum (II) complexes: Synthesis and evaluation of binding affinity for estrogen receptors and the effect on breast cancer MCF-7 cells
Spyriounis,Demopoulos,Kourounakis,Kouretas,Kortsaris,Antonoglou
, p. 301 - 305 (1992)
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One-pot ethynylation and catalytic desilylation in synthesis of mestranol and levonorgestrel
Wong, Fung Fuh,Chuang, Shih Hsien,Yang, Sheng-chuan,Lin, Yu-Hsiang,Tseng, Wen-Che,Lin, Shao-Kai,Huang, Jiann-Jyh
, p. 4068 - 4072 (2010)
A one-pot ethylnylation and catalytic desilylation reaction was developed for the synthesis of mestranol and levonorgestrel. Addition of trimethylsilylacetylide to the carbonyl group at C-17 of the steroids yielded the C-17α-trimethylsilylacetylenyl adducts, which were desilylated with a catalytic amount of TBAF (0.050 equiv) in one pot to provide the corresponding mestranol and levonorgestrel both in 90% yields. A plausible mechanism was proposed for the catalytic desilylation through the regeneration of the fluoride ion from the reaction of alkoxide on the steroid with Me3SiF. The one-pot ethynylation and catalytic desilylation methodology provided an alternative route and avoided the traditional use of flammable and explosive acetylene gas toward the synthesis of mestranol and levonorgestrel.
N-butyl, N-methyl, 11-[3′, 17′ β-(dihydroxy)-1′,3′,5′(10′)-estratrien-16′ α-yl]-9(R/S)-bromo undecanamide: Synthesis and 17β-HSD inhibiting, estrogenic and antiestrogenic activities
Pelletier, Joelle D.,Labrie, Fernand,Poirier, Donald
, p. 536 - 547 (1994)
The synthesis of a 16α-(bromoalkylamide) derivative of estradiol (N-butyl, N-methyl, 11-[3′,17′ β-(dihydroxy)-1′,3′,5′ (10′)-estratrien-16′ α-yl]-9 (R/S)-bromo undecanamide) was performed by two different approaches starting from estrone. Each approach has the same key intermediate, containing an aldehyde group, but differs by the bromination step and the timing of formation of the amide group. This compound was found to cause, at 100 ·M, a complete inhibition of 17β-hydroxysteroid dehydrogenase (17β-HSD) responsible for the interconversion of estrone and estradiol. The corresponding IC50 value was 10.6 ·M. In the estrogen-sensitive ZR-75-1 human breast cancer cell line, this estradiol derivative has no estrogenic activity at 30 nM and only a minimal estrogenic activity (10% above the basal level) at l ·M. At this latter concentration, this compound causes a 28% inhibition of 0.1 nM E2-induced cell proliferation (antiestrogenic activity). Thus, the introduction of a side-chain with a secondary bromide and a butyl methyl amide group at the 16α-position of estradiol has two interesting effects; namely an inhibition of cytosolic 17β-HSD and a blockade of the estrogenic effect of estradiol. (Steroids 59:536-547, 1994).
D-ring allyl derivatives of 17β- and 17α-estradiols: Chemical synthesis and 13C NMR data
Dionne, Patricia,Ngatcha, Beatrice Tchedam,Poirier, Donald
, p. 674 - 681 (1997)
We report the 13 C NMR data for 17β-estradiol, 17α-estradiol, and a series of ten 17β- or 17α-estradiol derivatives bearing an allyl group on the D-ring (at C-17, C-16, and C-15 positions). The target 17β-OH estradiol derivatives were synthesized from estrone by well known obtained by a modified Mitsunoba alcohol inversion of the allyl group (17α, 17β, 16α, 16β, and 15β) and two alcohol stereochemistries (17β and 17α) of the D- ring were studied, resulting in an important source of data. The effect of allyl-positioning and alcohol stereochemistry on 13C NMR chemical shifts was also identified, producing important points of comparison for other steriod analogs.
E-Ring extended estrone derivatives: introduction of 2-phenylcyclopentenone to the estrone D-ring via an intermolecular Pauson-Khand reaction
Kaasalainen, Emmi,Tois, Jan,Russo, Luca,Rissanen, Kari,Helaja, Juho
, p. 5669 - 5672 (2006)
An expedient synthetic route to E-ring extended estrone derivatives is reported. Estrone-derived cyclopentenones were accessed by an intermolecular Pauson-Khand (PK) cycloaddition. It was found that electron donating and withdrawing substituents in the arylalkyne increased and decreased the yields of PK products, respectively. The stereochemistry of the products was elucidated by X-ray and NMR studies.
A concise stereocontrolled total synthesis of (+)-estrone
Takano,Moriya,Ogasawara
, p. 1909 - 1910 (1992)
(+)-Estrone (1) has been synthesized in diastereo- and regioselective manners in six steps in 28% overall yield (38% based on the consumed material) starting from (-)-dicyclopentadienone (2) by employing a Diels-Alder cycloaddition-cycloreversion as the key step.
Enantioconvergent synthesis of (+)-estrone from racemic 4-tert-butoxy-2-cyclopentenone
Sugahara, Tsutomu,Ogasawara, Kunio
, p. 7403 - 7406 (1996)
(+)-Estrone has been synthesized in an enantioconvergent manner from racemic 4-tert-butoxy-2-cyclopentenone via contrasteric Diels-Alder reaction and lipase-mediated kinetic transesterification as the key steps.
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Ringold et al.
, p. 2477 (1956)
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Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain
Kopel, Lucas C.,Ahmed, Mahmoud S.,Halaweish, Fathi T.
, p. 1119 - 1125 (2013)
Functionalized estrogen analogs have received interest due to their unique and differing biological activity compared to their parent compounds. The synthesis of a new class of 3-methoxyestrone analogs functionalized at the C17 position possessing both alkyl and aryl substituted α,β-unsaturated ketones is described, along with their thiophenol conjugate addition products.
Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation
Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng
, p. 4018 - 4022 (2021/05/26)
Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.
Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl
Zhao, Jianyou,Shen, Tong,Sun, Zhihui,Wang, Nengyong,Yang, Le,Wu, Jintao,You, Huichao,Liu, Zhong-Quan
supporting information, p. 4057 - 4061 (2021/05/26)
A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.
Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism
Sueki, Shunsuke,Matsuyama, Mizuki,Watanabe, Azumi,Kanemaki, Arata,Katakawa, Kazuaki,Anada, Masahiro
, p. 4878 - 4885 (2020/06/02)
Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.
