38937-66-5Relevant articles and documents
An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
Mocci, Rita,De Luca, Lidia,Delogu, Francesco,Porcheddu, Andrea
supporting information, p. 3135 - 3144 (2016/10/09)
An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).
Cross metathesis with hydroxamate and benzamide BOC-protected alkenes to access HDAC inhibitors and their biological evaluation highlighted intrinsic activity of BOC-protected dihydroxamates
Zwick, Vincent,Nurisso, Alessandra,Sim?es-Pires, Claudia,Bouchet, Samuel,Martinet, Nadine,Lehotzky, Attila,Ovadi, Judit,Cuendet, Muriel,Blanquart, Christophe,Bertrand, Philippe
supporting information, p. 154 - 159 (2015/12/18)
Conditions for the metathesis of alkenes in the convergent synthesis of HDAC inhibitors have been improved by continuous catalyst flow injection in the reaction media. Intermediate and target compounds obtained were tested for their ability to induce HDAC
A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines
Ohtsuka, Naoya,Okuno, Moriaki,Hoshino, Yujiro,Honda, Kiyoshi
supporting information, p. 9046 - 9054 (2016/10/05)
A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.
An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii
Chung, Yu-Ming,Wei, Chien-Kei,Chuang, Da-Wei,El-Shazly, Mohamed,Hsieh, Chi-Ting,Asai, Teigo,Oshima, Yoshiteru,Hsieh, Tusty-Jiuan,Hwang, Tsong-Long,Wu, Yang-Chang,Chang, Fang-Rong
supporting information, p. 3866 - 3872 (2013/07/19)
The addition of a DNA methyltransferase inhibitor, 5-azacytidine, to Aspergillus sydowii fungus culture broth changed its secondary metabolites profile. Analysis of the culture broth extract led to the isolation of three new bisabolane-type sesquiterpenoids: (7S)-(+)-7-O-methylsydonol (1), (7S,11S)-(+)-12-hydroxysydonic acid (2) and 7-deoxy-7,14-didehydrosydonol (3), along with eight known compounds. The isolated compounds were evaluated for their anti-diabetic and anti-inflammatory activities. Among the isolates, (S)-(+)-sydonol (4) did not only potentiate insulin-stimulated glucose consumption but also prevented lipid accumulation in 3T3-L1 adipocytes. Additionally, (S)-(+)-sydonol (4) exhibited significant anti-inflammatory activity through inhibiting superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils. This is the first report on isolating a secondary metabolite with anti-diabetic and anti-inflammatory activities from microorganisms.
Modified cap group suberoylanilide hydroxamic acid histone deacetylase inhibitor derivatives reveal improved selective antileukemic activity
Salmi-Smail, Chanaz,Fabre, Aurélie,Dequiedt, Franck,Restouin, Audrey,Castellano, Rémy,Garbit, Slaveia,Roche, Philippe,Morelli, Xavier,Brunel, Jean Michel,Collette, Yves
experimental part, p. 3038 - 3047 (2010/09/07)
A series of SAHA cap derivatives was designed and prepared in good-to-excellent yields that varied from 49% to 95%. These derivatives were evaluated for their antiproliferative activity in several human cancer cell lines. Antiproliferative activity was observed for concentrations varying from 0.12 to >100 μM, and a molecular modeling approach of selected SAHA derivatives, based on available structural information of human HDAC8 in complex with SAHA, was performed. Strikingly, two compounds displayed up to 10-fold improved antileukemic activity with respect to SAHA; however, these compounds displayed antiproliferative activity similar to SAHA when assayed against solid tumor-derived cell lines. A 10-fold improvement in the leukemic vs peripheral blood mononuclear cell therapeutic ratio, with no evident in vivo toxicity toward blood cells, was also observed. The herein-described compounds and method of synthesis will provide invaluable tools to investigate the molecular mechanism responsible for the reported selectively improved antileukemic activity.
Synthesis of hydroxamic acids by activation of carboxylic acids with N,N'-carbonyldiimidazole: Exploring the efficiency of the method
Usachova, Natalija,Leitis, Gundars,Jirgensons, Aigars,Kalvinsh, Ivars
experimental part, p. 927 - 935 (2010/05/01)
Activation of carboxylic acids with N,N'-carbonyldiimidazole followed by the reaction with anhydrous or aqueous hydroxylamine hydrochloride was demonstrated to be an operationally simple method for the synthesis of hydroxamic acids in good yield and high purity after aqueous workup. The potential by-product, N,O-diacylhydroxylamine, is cleanly transformed to hydroxamic acid in these reaction conditions.
Hydroxamic acids as a novel family of serine racemase inhibitors: Mechanistic analysis reveals different modes of interaction with the pyridoxal-5′-phosphate cofactor
Hoffman, Hillary E.,Jirásková, Jana,Cígler, Petr,?anda, Miloslav,Schraml, Jan,Konvalinka, Jan
experimental part, p. 6032 - 6041 (2010/03/24)
Mammalian serine racemase (SR) is a pyridoxal-5′-phosphate (PLP) dependent enzyme responsible for the biosynthesis of the neurotransmitter D-serine, which activates N-methyl-D-aspartate (NMDA) receptors in the CNS. Aberrant regulation of NMDA receptor signaling has been implicated in a variety of neuropathologies, and inhibitors of SR would therefore be a worthwhile tool for further investigation or treatment of such conditions. Here, we identify a series of small aliphatic hydroxamic acids (HAs) that act as potent SR inhibitors. However, specificity studies showed that some of these HAs can act as nonspecific inhibitors of PLP-dependent enzymes. We employed NMR, MS, and UV/vis spectroscopic techniques to reveal that the nonspecific effect is likely due to irreversible interaction of the HA moiety with PLP to form aldoxime species. We also characterize L-aspartic acid β-hydroxamate as a competitive and selective SR inhibitor that could be used as a scaffold for further inhibitor development. 2009 American Chemical Society.
Conformational behaviour of hydroxamic acids: Ab initio and structural studies
Brown, David A.,Coogan, Raymond A.,Fitzpatrick, Noel J.,Glass, William K.,Abukshima, Dau E.,Shiels, Loreto,Ahlgren, Markku,Smolander, Kimmo,Pakkanen, Tuula T.,Pakkanen, Tapani A.,Peraekylae, Mikael
, p. 2673 - 2679 (2007/10/03)
The conformational behaviour of a series of monohydroxamic acids, p-RC6H4CONR 'OH (R = Me, R' = H Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)n (CONR'OH)2 (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy. X-Ray crystal structure determinations of p-MeC6H4CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the so id state and solution. The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.
A FACILE SYNTHESIS OF ALIPHATIC DIHYDROXAMIC ACIDS OF GENERAL FORMULA RONR'-CO-(CH2)n-CO-NR'OR
Brown, D. A.,Geraty, R. A.,Glennon, J. D.,Choileain, N. Ni
, p. 1159 - 1164 (2007/10/02)
Synthesis of dihydroxamic acids using dicarboxylic acids and N,N'-carbonyldiimidazole.
Synthesis of Some Dihydroxamic Acid Siderophores
Das, M. K.,Bose, P.,Roy, N.
, p. 345 - 348 (2007/10/02)
Twenty-two new dihydroxamic acids having the general formula (CH2)n2 (n = 2, 3, 4, 6, 8; R = H, aryl) have been synthesized either by condensation of the acid chlorides with suitable arylhydroxylamines or by the reaction of the esters with hydroxylamine and characterized by elemental analyses and infrared, UV, and proton NMR spectra.
