59864-01-6Relevant academic research and scientific papers
Synthesis of thiazolyl-based hydroxamic acids as histone deacetylase inhibitors
Alves-Avelar, Leandro A.,Asfaha, Yodita,Horstick-Muche, Nadine,Kassack, Matthias U.,Klinken, Stefan,Kurz, Thomas,Lungerich, Beate,Skerhut, Alexander Jan
, p. 1 - 13 (2020/12/15)
Herein we report the synthesis of 4-phenyl substituted thiazolyl-based hydroxamates as histone deacetylase inhibitors. The synthesis of the target compounds is comprised of a Hantzsch-thiazole reaction, a HATU-mediated acylation and a hydroxamic acid synthesis. Preliminary docking results indicated an isozyme selectivity by addressing the lower pocket of HDAC4 with 4-phenyl thiazoles. Surprisingly, this new series of thiazolyl based hydroxamates revealed a moderate HDAC6 inhibitory activity in the low micromolar range. Two of the hydroxamic acids did not show an HDAC4 inhibition up to 100 μM, whilst a third with a 4-pyridinyl CAP moiety displayed a moderate HDAC4 inhibitory activity in the micromolar range.
One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
, p. 5827 - 5832 (2017/09/09)
Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
