N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones

2021 ◽  
Vol 19 (11) ◽  
pp. 2442-2447
Author(s):  
Daisuke Shimbo ◽  
Toshifumi Maruyama ◽  
Norihiro Tada ◽  
Akichika Itoh
Keyword(s):  
Amino Acids ◽  
Hydroxamic Acid ◽  
Hydroxamic Acids ◽  
Hydroxamic Acid Derivatives

Ethynyl benziodoxolone enabled the chemoselective N-functionalization of O-alkyl hydroxamic acids derived from amino acids and pharmaceuticals. The synthesized cis-vinyl benziodoxolone was derivatized to hydroxamic acid-derived enamides.

Nonenzymatic Catalysis by Metal Ions and Phosphoric Acid Esters of Hydroxamic Acid Formation

1980 ◽  
Vol 35 (6) ◽  
pp. 727-730
Author(s):  
Oemer Saygin ◽  
Peter Decker
Keyword(s):  
Amino Acids ◽  
Phosphoric Acid ◽  
Metal Ions ◽  
Inorganic Phosphate ◽  
Hydroxamic Acid ◽  
Hydroxamic Acids ◽  
Bivalent Ions ◽  
No Release ◽  
Catalytic Effects ◽  
Acid Esters

Abstract Nonenzymatic catalysis by bivalent ions of Be, Mg, Ca, Zn, Mn, Ni and Co and bioorganic phosphates of the formation of hydroxamic acids from acetate or amino acids has been studied systematically. Increased yields of hydroxamate were observed at particular combinations of reactants. The most prominent increase (ca. 15-fold) was found with acetate and Ni++, and with a combination of ATP and Be++. Among others especially ribose-5-phosphate and glucose-5-phosphate enhanced yields in the presence of most metal ions. Since no release of inorganic phosphate was observed, this effect cannot be interpreted as an evidence for intermediate transhosphorylation reactions; it may also result from simple catalytic effects of metal sugar complexes.

Formation of unusual side-products from succinimidyl esters of fatty acids during the acylation of amino acids

1982 ◽  
Vol 60 (14) ◽  
pp. 1806-1808 ◽  
Author(s):  
Alenka Paquet ◽  
Michel Bergeron
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Methyl Ester ◽  
Palmitic Acid ◽  
Sodium Hydroxide ◽  
Hydroxamic Acid ◽  
Aqueous Sodium Hydroxide ◽  
Side Product ◽  
Aqueous Sodium ◽  
Hydroxamic Acid Derivatives

A new side-product, succinohydroxamic decanoic anhydride, was isolated from the reaction mixture during the acylation of lysine by succinimidyl decanoate in the presence of aqueous sodium hydroxide. Laurie and palmitic acid derivatives were also obtained. It is shown that these compounds can be used for acylation of amino acids. The hydroxamic acid derivatives were also detected when the acylations by succinimidyl esters of fatty acids were carried out under anhydrous conditions. Preparation of N-lauroyl-L-tyrosine methyl ester from tyrosine methyl ester and succinimidyl laurate is also described.

Inhibition of Urease Activity by Hydroxamic Acid Derivatives of Amino Acids

1975 ◽  
Vol 77 (4) ◽  
pp. 837-843 ◽  
Author(s):  
Kyoichi KOBASHI ◽  
Sachiko TAKEBE ◽  
Nobuo TERASHIMA ◽  
Jun'ichi HASE
Keyword(s):  
Amino Acids ◽  
Hydroxamic Acid ◽  
Urease Activity ◽  
Derivatives Of ◽  
Hydroxamic Acid Derivatives

Hydroxamic acids. III. Mass spectra of substituted hydroxamic acids and cyclic imides

1969 ◽  
Vol 22 (1) ◽  
pp. 175 ◽  
Author(s):  
JH Bowie ◽  
MTW Hearn ◽  
AD Ward
Keyword(s):  
Electron Impact ◽  
Hydroxamic Acid ◽  
Mass Spectra ◽  
Hydroxamic Acids ◽  
Skeletal Rearrangement ◽  
Cyclic Imides ◽  
Derivatives Of ◽  
Hydroxamic Acid Derivatives

Aryl hydroxamic acid derivatives fragment in a diagnostic manner upon electron impact. A hydroxamic acid containing both styryl and benzyl substituents undergoes skeletal-rearrangement of the type ABC → AC+B. The mass spectra of the O- and N-acetyl derivatives of O- benzylhydroxamic acids are indistinguishable. M-CO2 fragments are again observed in the mass spectra of several substituted phthalimides.

Design, synthesis, and preliminary bioactivity studies of substituted purine hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors

MedChemComm ◽  
2014 ◽  
Vol 5 (12) ◽  
pp. 1887-1891 ◽  
Author(s):  
Junhua Wang ◽  
Feng'e Sun ◽  
Leiqiang Han ◽  
Xuben Hou ◽  
Xiaole Pan ◽  
...  
Keyword(s):  
Histone Deacetylase ◽  
Hydroxamic Acid ◽  
Tumor Therapy ◽  
Hdac Inhibitors ◽  
Hydroxamic Acids ◽  
Hdac Inhibition ◽  
Design Synthesis ◽  
Hydroxamic Acid Derivatives

Histone deacetylase (HDAC) is a clinically validated target for anti-tumor therapy. In order to increase HDAC inhibition and efficiency, we developed a series of novel substituted purine hydroxamic acids as potent HDAC inhibitors.

scholarly journals Cross metathesis-mediated synthesis of hydroxamic acid derivatives

2018 ◽  
Vol 14 ◽  
pp. 3070-3075 ◽  
Author(s):  
Shital Kumar Chattopadhyay ◽  
Subhankar Ghosh ◽  
Suman Sil
Keyword(s):  
Hydroxamic Acid ◽  
Cyclic Peptide ◽  
Alternative Synthesis ◽  
Acid Component ◽  
Cross Metathesis ◽  
Reaction Proceeds ◽  
Amino Acid Component ◽  
Short Time ◽  
Unusual Amino Acid ◽  
Hydroxamic Acid Derivatives

An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and N-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs’ second generation catalyst within short time and in good yields (57–85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good yield (70–89%). An important demonstration of the protocol is the preparation of the unusual amino acid component of the bioactive cyclic peptide Chap-31.

Olaparib hydroxamic acid derivatives as dual PARP and HDAC inhibitors for cancer therapy

2017 ◽  
Vol 25 (15) ◽  
pp. 4100-4109 ◽  
Author(s):  
Zigao Yuan ◽  
Shaopeng Chen ◽  
Qinsheng Sun ◽  
Ning Wang ◽  
Dan Li ◽  
...  
Keyword(s):  
Cancer Therapy ◽  
Hydroxamic Acid ◽  
Hdac Inhibitors ◽  
Hydroxamic Acid Derivatives
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