Synthesis on novel Tamoxifen derivatives

Rey, Jullien; Hu, Haipeng; Snyder, James P.; Barrett, Anthony G. M.

doi:10.1016/j.tet.2012.08.089

Cited by 12 publications

(9 citation statements)

References 22 publications

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“…Reductive cross coupling of phthalimides with carbonyl compounds is a useful method for the synthesis of 3-substituted isoindoline-1-ones. To date, this type of reaction has been effected using SmI 2 as a reducing agent and electroreduction, and applied to the synthesis of isoindolone alkaloids. , On the other hand, low-valent titanium is well-known as a powerful reagent for the reductive cross coupling of two different carbonyl compounds. , Recently, we also reported the reductive coupling of uracils and N -methoxycarbonyl lactams with benzophenones by low-valent titanium. In this paper, we report the reductive coupling of phthalimides with ketones and aldehydes by low-valent titanium generated from Zn-TiCl 4 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones

2013

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The reductive coupling of phthalimides with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydroxy-3-(1-hydroxyalkyl)isoindolin-1-ones and alkylideneisoindolin-1-ones, selectively by controlling the reaction conditions. Therefore, the one-pot synthesis of alkylideneisoindolin-1-ones from phthalimides was effected by this reaction. Although the alkylideneisoindolin-1-ones prepared from phthalimides and aldehydes were formed as mixtures of geometric isomers in most cases, the geometric ratios could be increased by reflux in cat. PPTS/toluene. After the isomerization, the E-isomers of N-methyl substituted alkylideneisoindolin-1-ones (X = Me, R(1) = R, R(2) = H) and the Z-isomers of N-unsubstituted alkylideneisoindolin-1-ones (X = H, R(1) = H, R(2) = R) were obtained preferentially.

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Section: Introductionmentioning

confidence: 99%

Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones

2013

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“…27,28 Hydrocarbon bromide 16 was refluxed with Mg turnings to prepare the corresponding Grignard reagent, and the following addition to (S)-3-methylheptanal (11) afforded (5S,9S)-5,9-dimethyloctadec-17-en-7-ol (17) (78% yield, dr = 1.8:1 determined by its 13 C NMR spectra). 29 The final mesylation with MsCl 30 and reduction with LiAlH 4 provided a mixture of (10S,14S)-10,14-dimethyloctadec-1-ene (1) and olefinic byproduct. 31 To remove the olefinic byproduct, we treated the mixture with m-CPBA and afforded the desired pheromone 1 (21% yield two steps).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella

Yuan

Liu

et al. 2022

Chirality

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“…This condition provides the highest yield and minimal E / Z isomerization. Monoalkylated compounds 27 and 38 were prepared using a reported protocol that utilizes an equivalent ratio of potassium carbonate and alkyl chloride in acetone–water system for 2 h under dark conditions . Dialkylated substituents 28 and 29 were obtained under similar reaction conditions but with excessive alkyl chloride and long-time refluxing.…”

Section: Resultsmentioning

confidence: 99%

Screening and Reverse-Engineering of Estrogen Receptor Ligands as Potent Pan-Filovirus Inhibitors

Cooper

Schafer

et al. 2020

J. Med. Chem.

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Filoviridae, including Ebola (EBOV) and Marburg (MARV) viruses, are emerging pathogens that pose a serious threat to public health. No agents have been approved to treat filovirus infections, representing a major unmet medical need. The selective estrogen receptor modulator (SERM) toremifene was previously identified from a screen of FDA-approved drugs as a potent EBOV viral entry inhibitor, via binding to EBOV glycoprotein (GP). A focused screen of ER ligands identified ridaifen-B as a potent dual inhibitor of EBOV and MARV. Optimization and reverseengineering to remove ER activity led to a novel compound 30 showing potent inhibition against infectious EBOV Zaire (0.09 μM) and MARV (0.64 μM). Mutagenesis studies confirmed that inhibition of EBOV viral entry is mediated by direct interaction with GP. Importantly, compound 30 (XL-147) displayed broad-spectrum anti-filovirus activity against Bundibugyo, Tai Forest, Reston, and Měnglà viruses, and is the first sub-micromolar antiviral agent reported for some of these strains, therefore warranting further development as a pan-filovirus inhibitor.

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Synthesis on novel Tamoxifen derivatives

Cited by 12 publications

References 22 publications

Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones

Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones

Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella

Screening and Reverse-Engineering of Estrogen Receptor Ligands as Potent Pan-Filovirus Inhibitors

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