80213-01-0Relevant articles and documents
Photoredox Polyfluoroarylation of Alkyl Halides via Halogen Atom Transfer
Blackburn, Bryan G.,Cooke, Maria Victoria,Laulhé, Sébastien,Niu, Ben,Sachidanandan, Krishnakumar
supporting information, p. 916 - 920 (2022/02/07)
Polyfluoroarene moieties are of interest in medicinal chemistry, agrochemicals, and material sciences. Herein, we present the first polyfluoroarylation of unactivated alkyl halides via a halogen atom transfer process. This method converts primary, secondary, and tertiary alkyl halides into the respective polyfluoroaryl compounds in good yields in the presence of amide, carbamate, ester, aromatic, and sulfonamide moieties, including derivatives of complex bioactive molecules. Mechanistic work revealed that this transformation proceeds through an alkyl radical generated after the halogen atom transfer.
Investigation of the effect of different linker chemotypes on the inhibition of histone deacetylases (HDACs)
Linciano, Pasquale,Benedetti, Rosaria,Pinzi, Luca,Russo, Fabiana,Chianese, Ugo,Sorbi, Claudia,Altucci, Lucia,Rastelli, Giulio,Brasili, Livio,Franchini, Silvia
, (2020/11/24)
Histone Deacetylases (HDACs) are among the most attractive and interesting targets in anticancer drug discovery. The clinical relevance of HDAC inhibitors (HDACIs) is testified by four FDA-approved drugs for cancer treatment. However, one of the main drawbacks of these drugs resides in the lack of selectivity against the different HDAC isoforms, resulting in severe side effects. Thus, the identification of selective HDACIs represents an exciting challenge for medicinal chemists. HDACIs are composed of a cap group, a linker region, and a metal-binding group interacting with the catalytic zinc ion. While the cap group has been extensively investigated, less information is available about the effect of the linker on isoform selectivity. To this aim, in this work, we explored novel linker chemotypes to direct isoform selectivity. A small library of 25 hydroxamic acids with hitherto unexplored linker chemotypes was prepared. In vitro tests demonstrated that, depending on the linker type, some candidates selectively inhibit HDAC1 over HDAC6 isoform or vice versa. Docking calculations were performed to rationalize the effect of the novel linker chemotypes on biologic activity. Moreover, four compounds were able to increase the levels of acetylation of histone H3 or tubulin. These compounds were also assayed in breast cancer MCF7 cells to test their antiproliferative effect. Three compounds showed a significant reduction of cancer proliferation, representing valuable starting points for further optimization.
Stereoselective direct reductive amination of ketones with electron-deficient amines using Re2O7/NaPF6 catalyst
Das, Braja Gopal,Ghorai, Prasanta
supporting information, p. 4379 - 4382 (2013/08/23)
The first example of direct reductive amination (DRA) of ketones with electron-deficient amines (EDA) such as Cbz-, Boc-, EtOCO-, Fmoc-, Bz-, ArSO2-, etc. protected amines have been achieved using catalytic Re2O7/NaPF6. Excellent chemoselectivities as well as diastereoselectivity (for 2-alkyl cyclohexanones) were obtained. The Royal Society of Chemistry 2013.
Nickel-Catalyzed reductive cross-Coupling of unactivated alkyl halides
Yu, Xiaolong,Yang, Tao,Wang, Shulin,Xu, Hailiang,Gong, Hegui
, p. 2138 - 2141 (2011/06/22)
A Ni-catalyzed reductive approach to the cross-coupling of two unactivated alkyl halides has been successfully developed. The reaction works efficiently for primary and secondary halides, with at least one being bromide. The mild reaction conditions allow for excellent functional group tolerance and provide the C(sp3)-C(sp3) coupling products in moderate to excellent yields.
Highly chemoselective metal-free reduction of tertiary amides
Barbe, Guillaume,Charette, Andre B.
, p. 18 - 19 (2008/09/20)
This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines. Hantzsch ester is used as a mild reducing agent for the reduction of trifluoromethanesulfonic anhydride activated amides providing the tertiary amines with high functional group tolerance. Copyright
Practical Syntheses of N-Substituted 3-Hydroxyazetidines and 4-Hydroxypiperidines by Hydroxylation with Sphingomonas sp. HXN-200
Chang, Dongliang,Feiten, Hans-Juergen,Engesser, Karl-H.,Van Beilen, Jan B.,Witholt, Bernard,Li, Zhi
, p. 1859 - 1862 (2007/10/03)
(Equation Presented) Hydroxylation of N-substituted azetidines 11 and 12 and piperidines 15-19 with Sphingomonas sp. HXN-200 gave 91-98% of the corresponding 3-hydroxyazetidines 13 and 14 and 4-hydroxypiperidines 20-24, respectively, with high activity and excellent regioselectivity. High yields and high product concentrations (2 g/L) were achieved with frozen/thawed cells as biocatalyst. For the first time, rehydrated lyophilized cells were successfully used for the biohydroxylation.
A new paradigm for biohydroxylation by Beauveria bassiana ATCC 7159
Holland, Herbert L.,Morris, Terence A.,Nava, Phillip J.,Zabic, Mirjana
, p. 7441 - 7460 (2007/10/03)
The biohydroxylation of a series of amides and related amino, keto and hydrocarbon substrates by the fungal biocatalyst Beauveria bassiana ATCC 7159 has been examined. The product distributions, together with data obtained from selective inhibition experiments using the cyt.P-450 inhibitors isosafrole, 1-aminobenzotriazole and phenylacetylene, suggest that B. bassiana contains a range of hydroxylase enzymes with different substrate specificities. A paradigm is presented for the interpretation of the results of microbial hydroxylation and for the application of existing active site models for B. bassiana.
Biohydroxylation reactions catalyzed by enzymes and whole-cell systems
Flitsch, Sabine L.,Aitken, Suzanne J.,Chow, Cathy S.-Y.,Grogan, Gideon,Staines, Adam
, p. 81 - 90 (2007/10/03)
The biohydroxylation of a number of cyclic substrates (3-24) containing aromatic side chains was used to compare substrate specificity and selectivity of hydroxylation using microbial enzymes and whole-cell biocatalysts. In general, the regioselectivity of reaction was remarkably similar between the different catalysts in that little aromatic or benzylic, but significant aliphatic hydroxylation was observed. However, a more detailed investigation of isolated products showed complementary substrate specificity, functional group compatibility, and regioselectivity of hydroxylation. Substrate specificity and regioselectivity could be further modulated by small changes to the nature of the aromatic side chain, which appears to play an important role in substrate recognition.
Ruthenium-Catalyzed Oxidations of Alcohols
Murahashi,Naota
, p. 203 - 213 (2007/10/03)
A combination of low-valent ruthenium complexes and peroxides such as t-BuOOH and peracids serves as efficient catalytic systems for the oxidation of aromatic and aliphatic hydroxy compounds. The utility of these methods was demonstrated by the synthesis of acyl cyanides which are versatile synthetic intermediates. The principle of the catalytic oxidations with peracids lead to the novel and efficient method for aerobic oxidation of alcohols in the presence of aldehydes. This reaction is of importance in synthetic and large scale industrial processes and from environmental points of view. The present principle will provide new chemistry of oxidative transformations of various industrially important functional materials.
MICROBIOLOGICAL TRANSFORMATION OF NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS. 3. MICROBIOLOGICAL SYNTHESIS OF HYDROXY DERIVATIVES OF 1-BENZOYLPIPERIDINE AND 1-BENZOYLPYRROLIDINE
Parshikov, I.A.,Modyanova, L.V.,Dovgilivich, E.V.,Terent'ev, P.B.,Vorob'eva, L.I.,Grishina, G.V.
, p. 159 - 162 (2007/10/02)
The microbiological transformation of 1-benzoylpiperidine and 1-benzoylpyrrolidine by cultures of the fungi Aspergillus niger VKM F-1119 and Cunninghamella verticillata VKPM F-430 proceeds regio- and stereospecifically and leads respectively to the 4- and
