586-95-8Relevant academic research and scientific papers
New heterocyclic mono- and bis(α-hydroxymethyl)phosphinic acids: Synthesis and CuII binding abilities
Olszewski, Tomasz Krzysztof,Galezowska, Joanna,Boduszek, Bogdan,Kozlowski, Henryk
, p. 3539 - 3546 (2007)
A simple and efficient method for the synthesis of (α-hydroxymethyl) phosphinic acids in a pyridine and imidazole series from their corresponding aldehydes and aqueous hypophosphorous acid was developed. The same reaction carried out with an excess of aldehyde in the presence of a mineral acid led mainly to the corresponding bis(α-hydroxymethyl)phosphinic acids in moderate yields. The coordination properties of these compounds towards Cu II ions were determined. Additionally, it was found that [(hydroxy)-(2-pyridyl)- and (hydroxy)(4-pyridyl)methyl]phosphinic acids were easy to cleave in aqueous sulfuric acid solutions, to form phosphorus acid (H3PO3) and the corresponding pyridinemethanols. The kinetics of the cleavage reaction was studied. On the basis of the obtained results, a mechanism of the cleavage was formulated. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
, p. 1237 - 1242 (2021/06/01)
We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
Homoleptic cobalt(II) phenoxyimine complexes for hydrosilylation of aldehydes and ketones without base activation of cobalt(II)
Hori, Momoko,Ishikawa, Ryuta,Koga, Yuji,Matsubara, Kouki,Mitsuyama, Tomoaki,Shin, Sayaka
, p. 1379 - 1387 (2021/05/29)
Air-stable, easy to prepare, homoleptic cobalt(II) complexes bearing pendant-modified phenoxyimine ligands were synthesized and determined. The complexes exhibited high catalytic performance for reducing aldehydes and ketones via catalytic hydrosilylation, where a hydrosilane and a catalytic amount of the cobalt(II) complex were added under base-free conditions. The reaction proceeded even in the presence of excess water, and excellent functional-group tolerance was observed. Subsequent hydrolysis gave the alcohol in high yields. Moreover, H2O had a critical role in activation of the Co(II) catalyst with hydrosilane. Several additional results also indicated that the cobalt(II) center acts as an active catalyst in the hydrosilylation of aldehydes and ketones.
Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation
Relitti, Nicola,Saraswati, A. Prasanth,Chemi, Giulia,Brindisi, Margherita,Brogi, Simone,Herp, Daniel,Schmidtkunz, Karin,Saccoccia, Fulvio,Ruberti, Giovina,Ulivieri, Cristina,Vanni, Francesca,Sarno, Federica,Altucci, Lucia,Lamponi, Stefania,Jung, Manfred,Gemma, Sandra,Butini, Stefania,Campiani, Giuseppe
, (2020/11/24)
In this work we describe the synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors. The quinolone moiety has been exploited as an innovative bioactive cap-group for HDAC6 inhibition; its synthesis was achieved by applying a multicomponent reaction. The optimization of potency and selectivity of these products was performed by employing computational studies which led to the discovery of the diethylaminomethyl derivatives 7g and 7k as the most promising hit molecules. These compounds were investigated in cellular studies to evaluate their anticancer effect against colon (HCT-116) and histiocytic lymphoma (U9347) cancer cells, showing good to excellent potency, leading to tumor cell death by apoptosis induction. The small molecules 7a, 7g and 7k were able to strongly inhibit the cytoplasmic and slightly the nuclear HDAC enzymes, increasing the acetylation of tubulin and of the lysine 9 and 14 of histone 3, respectively. Compound 7g was also able to increase Hsp90 acetylation levels in HCT-116 cells, thus further supporting its HDAC6 inhibitory profile. Cytotoxicity and mutagenicity assays of these molecules showed a safe profile; moreover, the HPLC analysis of compound 7k revealed good solubility and stability profile.
Iron-catalyzed chemoselective hydride transfer reactions
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, (2021/06/07)
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?
Tanaka, Nao,Usuki, Toyonobu
, p. 5514 - 5522 (2020/07/24)
Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).
Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
Airoldi, Veronica,Piccolo, Oreste,Roda, Gabriella,Appiani, Rebecca,Bavo, Francesco,Tassini, Riccardo,Paganelli, Stefano,Arnoldi, Sebastiano,Pallavicini, Marco,Bolchi, Cristiano
supporting information, p. 162 - 168 (2019/12/11)
A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.
1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds
Johnson, Jahvon,Li, Sihan,Mo, Zixuan,Neary, Michelle C.,Zeng, Haisu,Zhang, Guoqi,Zheng, Shengping
supporting information, p. 2610 - 2615 (2020/03/05)
Reductive catalysis with earth-abundant metals is currently of increasing importance and shows potential in replacing precious metal catalysis. In this work, we revealed catalytic hydroboration and hydrosilylation of ketones and aldehydes achieved by a structurally defined manganese(ii) coordination polymer (CP) as a precatalyst under mild conditions. The manganese-catalysed methodology can be applied to a range of functionalized aldehydes and ketones with turnover numbers (TON) of up to 990. Preliminary results on the regioselective catalytic hydrofunctionalization of styrenes by the Mn-CP catalyst are also presented.
Catalyst-Free N-Deoxygenation by Photoexcitation of Hantzsch Ester
Cardinale, Luana,Jacobi Von Wangelin, Axel,Konev, Mikhail O.
supporting information, (2020/02/15)
A mild and operationally simple protocol for the deoxygenation of a variety of heteroaryl N-oxides and nitroarenes has been developed. A mixture of substrate and Hantzsch ester is proposed to result in an electron donor-acceptor complex, which upon blue-light irradiation undergoes photoinduced electron transfer between the two reactants to afford the products. N-oxide deoxygenation is demonstrated with 22 examples of functionally diverse substrates, and the chemoselective reduction of nitroarenes to the corresponding hydroxylamines is also shown.
Peptidomimetic Vinyl Heterocyclic Inhibitors of Cruzain Effect Antitrypanosomal Activity
Chenna, Bala C.,Li, Linfeng,Mellott, Drake M.,Zhai, Xiang,Siqueira-Neto, Jair L.,Calvet Alvarez, Claudia,Bernatchez, Jean A.,Desormeaux, Emily,Alvarez Hernandez, Elizabeth,Gomez, Jana,McKerrow, James H.,Cruz-Reyes, Jorge,Meek, Thomas D.
, p. 3298 - 3316 (2020/04/08)
Cruzain, an essential cysteine protease of the parasitic protozoan, Trypanosoma cruzi, is an important drug target for Chagas disease. We describe here a new series of reversible but time-dependent inhibitors of cruzain, composed of a dipeptide scaffold appended to vinyl heterocycles meant to provide replacements for the irreversible reactive "warheads" of vinyl sulfone inactivators of cruzain. Peptidomimetic vinyl heterocyclic inhibitors (PVHIs) containing Cbz-Phe-Phe/homoPhe scaffolds with vinyl-2-pyrimidine, vinyl-2-pyridine, and vinyl-2-(N-methyl)-pyridine groups conferred reversible, time-dependent inhibition of cruzain (Ki? = 0.1-0.4 μM). These cruzain inhibitors exhibited moderate to excellent selectivity versus human cathepsins B, L, and S and showed no apparent toxicity to human cells but were effective in cell cultures of Trypanosoma brucei brucei (EC50 = 1-15 μM) and eliminated T. cruzi in infected murine cardiomyoblasts (EC50 = 5-8 μM). PVHIs represent a new class of cruzain inhibitors that could progress to viable candidate compounds to treat Chagas disease and human sleeping sickness.
