1464-98-8Relevant academic research and scientific papers
Adenylation Activity of Carboxylic Acid Reductases Enables the Synthesis of Amides
Wood, Alexander J. L.,Weise, Nicholas J.,Frampton, Joseph D.,Dunstan, Mark S.,Hollas, Michael A.,Derrington, Sasha R.,Lloyd, Richard C.,Quaglia, Daniela,Parmeggiani, Fabio,Leys, David,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 14498 - 14501 (2017)
Carboxylic acid reductases (CARs) catalyze the reduction of a broad range of carboxylic acids to aldehydes using the cofactors adenosine triphosphate and nicotinamide adenine dinucleotide phosphate, and have become attractive biocatalysts for organic synthesis. Mechanistic understanding of CARs was used to expand reaction scope, generating biocatalysts for amide bond formation from carboxylic acid and amine. CARs demonstrated amidation activity for various acids and amines. Optimization of reaction conditions, with respect to pH and temperature, allowed for the synthesis of the anticonvulsant ilepcimide with up to 96 % conversion. Mechanistic studies using site-directed mutagenesis suggest that, following initial enzymatic adenylation of substrates, amidation of the carboxylic acid proceeds by direct reaction of the acyl adenylate with amine nucleophiles.
Gold catalysis: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects
Hashmi, A. Stephen K.,Weyrauch, Jan P.,Frey, Wolfgang,Bats, Jan W.
, p. 4391 - 4394 (2004)
(Chemical Equation Presented) 2,5-Disubstituted oxazoles are synthesized from the corresponding propargylcarboxamides under mild reaction conditions via homogeneous catalysis by AuCl3. While monitoring the conversion via 1H NMR spectroscopy, an intermediate 5-methylene-4,5-dihydrooxazole can be observed and accumulated up to 95%, being the first direct and catalytic preparative access to such alkylidene oxazolines. The intermediate was fully characterized and can be trapped at -25°C for several weeks. Deuteration experiments show a stereospecific mode of the two first steps of the reaction.
Efficient and general synthesis of 5-(alkoxycarbonyl)methylene-3-oxazolines by palladium-catalyzed oxidative carbonylation of prop-2-ynylamides
Bacchi, Alessia,Costa, Mirco,Gabriele, Bartolo,Pelizzi, Giancarlo,Salerno, Giuseppe
, p. 4450 - 4457 (2002)
A variety of prop-2-ynylamides have been carbonylated under oxidative conditions to give oxazolines, oxazolines with chelating groups, and bisoxazolines bearing an (alkoxycarbonyl)methylene chain at the 5 position in good yields. The cyclization-alkoxycarbonylation process was carried out in alcoholic media at 50-70°C and under 24 bar pressure of 3:1 carbon monoxide/air in the presence of catalytic amounts of 10% Pd/C or PdI2 in conjunction with KI. Cyclization occurred by anti attack of an oxygen function on the palladium-coordinated triple bond, followed by stereospecific alkoxycarbonylation, strictly resulting in E-stereochemistry. The structures of representative oxazolines and bisoxazolines have been determined by X-ray diffraction analysis.
Synthesis and biological evaluation of azamacrolide comprising the triazole moiety as quorum sensing inhibitors
Zhang, Bin,Guo, Bingyi,Bai, Yunlong,Lu, Huizhe,Dong, Yanhong
, (2018)
Novel azamacrolides comprising the triazole moiety were synthesized and evaluated for their quorum sensing inhibitor activities on the Agrobacterium tumefaciens. It was found that the inhibition rate of compound Z12-3 at 200 mg/L (0.45 mM) can reach 67%. The potential binding modes between these molecules and the TraR QS receptor was performed by molecular docking. The results showed that the two nitrogen atoms in the triazole ring of Z12-3 formed hydrogen bonds with GLN-2, and the carbonyl group (C=O) in the amide formed hydrogen bonds with water. It was worth noting that the carbonyl group on the macrolides formed hydrogen bonds with the G-106 base in the DNA. These azamacrolides may block quorum sensing expression through key amino acid residues or DNA bases in the TraR QS receptor by hydrogen-bonded.
Chemical modifications of poly(vinyl chloride) to poly(vinyl azide) and "clicked" triazole bearing groups for application in metal cation extraction
Ouerghui, Abid,Elamari, Hichem,Dardouri, Mokthar,Ncib, Sana,Meganem, Faouzi,Girard, Christian
, p. 191 - 197 (2016)
Chemical modification of poly(vinyl chloride) (PVC) by the replacement of chlorine atom presents a considerable interest in this work. In the first phase, PVC was partially azided with a sodium azide. Click-chemistry based on Copper (I)-catalyzed Huisgen'
Conjugation of a 5-nitrofuran-2-oyl moiety to aminoalkylimidazoles produces non-toxic nitrofurans that are efficacious in vitro and in vivo against multidrug-resistant Mycobacterium tuberculosis
Krasavin, Mikhail,Lukin, Alexei,Vedekhina, Tatiana,Manicheva, Olga,Dogonadze, Marine,Vinogradova, Tatiana,Zabolotnykh, Natalia,Rogacheva, Elizaveta,Kraeva, Liudmila,Yablonsky, Piotr
, p. 1115 - 1126 (2018)
Within the general nitrofuran carboxamide chemotype, chimera derivatives incorporating diversely substituted imidazoles attached via an alkylamino linker were synthesized. Antimycobacterial evaluation against drug-sensitive M. tuberculosis H37Rv strain id
Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
Brittain, William D. G.,Cobb, Steven L.
, p. 5793 - 5798 (2021/08/01)
This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives
He, Yuan,Liao, Xian-Zhang,Dong, Lin,Chen, Fen-Er
, p. 561 - 567 (2021/02/06)
Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.
COMPOUNDS FOR USE IN THE TREATMENT OF LIVER DISEASE
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Paragraph 00129-00130 00133, (2021/02/26)
Bile acid derivatives, methods of manufacture thereof, and uses thereof are disclosed herein. The bile acid derivatives have demonstrated potential as therapeutics for treating liver disease.
Water Can Accelerate Homogeneous Gold Catalysis
Hashmi, A. Stephen K.,Rudolph, Matthias,Stein, Philipp M.
supporting information, p. 4264 - 4271 (2021/08/03)
A selection of gold-catalyzed reactions was examined in a kinetic study on the influence of water on the rate constant. Two intramolecular reactions and one intermolecular reaction, which proceed via proton transfer and/or protodeauration steps, were inve
