13797-22-3Relevant articles and documents
3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor
Sit, Sing-Yuen,Ehrgott, Frederick J.,Gao, Jinnian,Meanwell, Nicholas A.
, p. 499 - 504 (1996)
A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [3H]-glycine and [3H]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [3H]-glycine with an IC50 of 29 nM.
Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
Cheng, Fei,Chen, Tao,Huang, Yin-Qiu,Li, Jia-Wei,Zhou, Chen,Xiao, Xiao,Chen, Fen-Er
supporting information, p. 115 - 120 (2022/01/04)
We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.
Novel N-aryl Oxamic Acids
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Paragraph 0045, (2021/10/11)
The present disclosure relates to novel N-aryl oxamic acid based inhibitors for Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB), and to the method of making and using the novel N-aryl oxamic acid based inhibitors. More specifically, compounds provided in this disclosure can be used to inhibit Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB) and to treat a patient having a Tuberculosis disease.
Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides
Gediya, Shweta K.,Vyas, Vijyesh K.,Clarkson, Guy J.,Wills, Martin
supporting information, p. 7803 - 7807 (2021/10/20)
The asymmetric transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which lead to the highest enantioselectivities in the products. The α-keto-amide reduction products have been converted to a range of synthetically valuable derivatives.
Visible light-mediated photocatalytic oxidative cleavage of activated alkynes: Via hydroamination: A direct approach to oxamates
Arepally, Sagar,Katta, Narenderreddy,Murugan, Arumugavel,Ojha, Mamata,Sharada, Duddu S.
, p. 12599 - 12603 (2020/04/24)
The direct oxidative cleavage of activated alkynes via hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an in situ formed enamine followed by radical coupling with an oxidant finally delivers the oxamate. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as a photocatalyst, and TBHP playing a dual role as O source and for the regeneration of the photocatalyst.
Highly Potent and Selective N-Aryl Oxamic Acid-Based Inhibitors for Mycobacterium tuberculosis Protein Tyrosine Phosphatase B
Ruddraraju, Kasi Viswanatharaju,Aggarwal, Devesh,Niu, Congwei,Baker, Erica Anne,Zhang, Ruo-Yu,Wu, Li,Zhang, Zhong-Yin
, p. 9212 - 9227 (2020/10/19)
Tuberculosis is an infectious disease caused by the bacterium Mycobacterium tuberculosis (Mtb). Mtb protein tyrosine phosphatase B (mPTPB) is a virulence factor required for Mtb survival in host macrophages. Consequently, mPTPB represents an exciting target for tuberculosis treatment. Here, we identified N-phenyl oxamic acid as a highly potent and selective monoacid-based phosphotyrosine mimetic for mPTPB inhibition. SAR studies on the initial hit, compound 4 (IC50 = 257 nM), resulted in several highly potent inhibitors with IC50 values lower than 20 nM for mPTPB. Among them, compound 4t showed a Ki of 2.7 nM for mPTPB with over 4500-fold preference over 25 mammalian PTPs. Kinetic, molecular docking, and site-directed mutagenesis analyses confirmed these compounds as active site-directed reversible inhibitors of mPTPB. These inhibitors can reverse the altered host cell immune responses induced by the bacterial phosphatase. Furthermore, the inhibitors possess molecular weights 0.43, and good aqueous solubility and metabolic stability, thus offering excellent starting points for further therapeutic development.
Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides
Zhang, Zhiguo,Gao, Xiaolong,Yu, Haifeng,Zhang, Guisheng,Liu, Jianming
, p. 3406 - 3411 (2018/07/31)
A copper-catalysed (diacetoxyiodo)benzene-promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open-air conditions and afforded methyl 2-oxo-2-(phenylamino)acetates in good to excellent yields combined with C?C σ-bond cleavage and formal oxidative C?H bond functionalization. A mechanism is proposed. (Figure presented.).
Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert -Butyl Hydroperoxide
Adib, Mehdi,Pashazadeh, Rahim,Gohari, Seyed Jamal Adin,Shahsavari, Fatemeh
supporting information, p. 1481 - 1485 (2017/08/15)
A novel tert -butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.
Ionic liquids based on oxalic acid mono amides
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Paragraph 0130; 0131, (2015/11/24)
The present invention relates to monosubstituted oxalic acid amides of the general formula (I) ????????[A]+ [O-C(O)-C(O)-X]-?????(I) wherein the meaning is for [A]+ a cation made from an organic moiety A having a formally positively charged heteroatom selected from the group consisting of nitrogen, phosphorus and sulfur and X is the group -NRaRb, wherein Ra and Rb are the same or different and are independently from each other hydrogen or a C1 to C30 organic residue with the proviso that at least one of Ra and Rb is a C1 to C30 organic residue.
Synthesis of N -arylisatins by the reaction of arynes with methyl 2-Oxo-2-(arylamino)acetates
Rogness, Donald C.,Larock, Richard C.
experimental part, p. 4980 - 4986 (2011/08/06)
N-Arylisatins are efficiently prepared by the reaction of 2-oxo-2-(arylamino)acetates and arynes under mild reaction conditions
