586-95-8Relevant articles and documents
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.
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.
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.