69849-48-5Relevant academic research and scientific papers
Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
Wang, Dong,Li, Linna,Feng, Hairong,Sun, Hua,Almeida-Veloso, Fabrice,Charavin, Marine,Yu, Peng,Désaubry, Laurent
, p. 2775 - 2780 (2018)
An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.
Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones: Via a Cu-catalyzed aerobic oxidative amidation
Cha, Hyojin,Chai, Jin Young,Chi, Dae Yoon,Kim, Hyeong Baik
supporting information, p. 4320 - 4326 (2021/05/31)
α-Ketoamides are an important key functional group and have been used as versatile and valuable intermediates and synthons in a variety of functional group transformations. Synthetic methods for making aryl α-ketoamides as drug candidates have been greatly improved through metal-catalyzed aerobic oxidative amidations. However, the preparation of alkyl α-ketoamides through metal-catalyzed aerobic oxidative amidations has not been reported because generating α-ketoamides from aliphatic ketones with two α-carbons theoretically provides two distinct α-ketoamides. Our strategy is to activate the α-carbon by introducing an N-substituent at one of the two α-positions. The key to this strategy is how heterocyclic compounds such as triazoles and imidazoles affect the selectivity of the synthesis of the alkyl α-ketoamides. From this basic concept, and by optimizing the reaction and elucidating the mechanism of the synthesis of aryl α-ketoamides via a copper-catalyzed aerobic oxidative amidation, we prepared fourteen aliphatic α-ketoamides in high yields (48-84%). This journal is
Alkyl keto-amide, amidoxime compound thereof, and preparation and application of compound
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Paragraph 0048, (2019/01/23)
The invention relates to alkyl keto-amide, an amidoxime compound thereof, and preparation and application of the compound. The alkyl keto-amide compound and a derivative thereof can be applied to metal palladium catalyzed C-H bond fluoridation, better rea
Synthesis, characterization and antitubercular activities of novel pyrrolyl hydrazones and their Cu-complexes
Joshi, Shrinivas D.,Kumar, Devendra,Dixit, Sheshagiri R.,Tigadi, Nageshwar,More, Uttam A.,Lherbet, Christian,Aminabhavi, Tejraj M.,Yang, Kap Seung
, p. 21 - 39 (2016/08/19)
Novel pyrrolyl hydrazones and their copper complexes have been synthesized and characterized using analytical and spectral techniques to show the tetrahedral geometry for Cu(II) complexes. Biological activities of hydrazones have been assessed to understand the role of metal ion on their biological activity and the effect of pyrrolyl hydrazones. In?vitro antitubercular activity against Mycobacterium tuberculosis of the metal complexes (13b and 13r) exhibited the highest antitubercular activity that are quite close to rifampicin (0.4?μg/mL), giving a MIC of 0.8?μg/mL. All other compounds showed good activity with the MIC values ranging from 1.6 to 100?μg/mL. A comparative study of inhibition values of the ligands and their complexes showed higher antimicrobial activity of the complexes than the ligands. Some compounds have a good activity against InhA and in particular, compounds 12r, 13b and 13r exhibited more than 60% binding with the enzyme even at 5?μM (exhibited good IC50 upto 2.4?μM). Most of the active molecules have a very less cytotoxicity against the human lung cancer cell-line A549. The docking and 3D-QSAR studies have been carried out to provide some insights into the mechanism of action for this class of compounds.
A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings
Goudedranche, Sbastien,Pierrot, David,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean
supporting information, p. 15605 - 15608 (2015/01/08)
We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic α-ketoamides with 1,3-bis-electrophilic enals. The obtained oxygen-bridged azepanes can be selectively transformed into optically active azepanone, azepanol or azepanedione derivatives of high synthetic value. This journal is
