Synthesis of Oxime Esters and Ethers as Potential Psychotropic Agents

Wylie, Billy B.; Isaacson, Eugene I.; Delgado, Jaime N.

doi:10.1002/jps.2600540932

Cited by 15 publications

(8 citation statements)

References 6 publications

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“…The hydrogen atom of the oxime OH group can be replaced with alkyl, acyl, or other substituents, and the general synthetic paths for O -substituted derivatives (oxime ethers or esters) include direct alkylation or acylation [ 76 ]. In addition, oximation of a corresponding aldehyde or ketone precursor by an appropriate O -substituted hydroxylamine is widely used (see, e.g., [ 38 , 77 ]).…”

Section: Chemical Characterization Of Oximesmentioning

confidence: 99%

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

et al. 2021

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Oximes have been studied for decades because of their significant roles as acetylcholinesterase reactivators. Over the last twenty years, a large number of oximes have been reported with useful pharmaceutical properties, including compounds with antibacterial, anticancer, anti-arthritis, and anti-stroke activities. Many oximes are kinase inhibitors and have been shown to inhibit over 40 different kinases, including AMP-activated protein kinase (AMPK), phosphatidylinositol 3-kinase (PI3K), cyclin-dependent kinase (CDK), serine/threonine kinases glycogen synthase kinase 3 α/β (GSK-3α/β), Aurora A, B-Raf, Chk1, death-associated protein-kinase-related 2 (DRAK2), phosphorylase kinase (PhK), serum and glucocorticoid-regulated kinase (SGK), Janus tyrosine kinase (JAK), and multiple receptor and non-receptor tyrosine kinases. Some oximes are inhibitors of lipoxygenase 5, human neutrophil elastase, and proteinase 3. The oxime group contains two H-bond acceptors (nitrogen and oxygen atoms) and one H-bond donor (OH group), versus only one H-bond acceptor present in carbonyl groups. This feature, together with the high polarity of oxime groups, may lead to a significantly different mode of interaction with receptor binding sites compared to corresponding carbonyl compounds, despite small changes in the total size and shape of the compound. In addition, oximes can generate nitric oxide. This review is focused on oximes as kinase inhibitors with anticancer and anti-inflammatory activities. Oximes with non-kinase targets or mechanisms of anti-inflammatory activity are also discussed.

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Section: Chemical Characterization Of Oximesmentioning

confidence: 99%

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

et al. 2021

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“…10 Aromatic benzophenone oxime esters and dibenzosuberone oxime esters are pharmacologically important. 11 Vanillin derived piperidin-4-one oxime esters have been tested for their antioxidant and antimicrobial potential. 12 The oxime pseudoesters derived from nafimidone have been tested as potential anticonvulsant compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity

Mehrez

Chakroun²,

Mtat

et al. 2020

JSCS

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A series of novel optically pure oxime pseudoesters derivatives were synthesized by the reaction of substitute keto oximes with various N-substituted α-amino acids chlorides in the presence of triethylamine and dichloromethane at 0 °C, and their structures were characterized by IR and 1D-NMR methods. The synthesized compounds were tested for their ability to inhibit the proliferation of human colon cancer cells and human epithelial cells. Some of them were revealed to have a significant cytotoxic effect.

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“…11 Aromatic benzophenone oxime esters and dibenzosuberone oxime esters are pharmacologically important. 12 Vanillinderived piperidin-4-one oxime esters have been tested for antioxidant and antimicrobial potential. 13 The oxime esters derived from nafimidone have been tested as potential anticonvulsant compounds.…”

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confidence: 99%

A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

Kumar

Srinivas

et al. 2014

Synthesis

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A facile access to the synthesis of alkyl and aryl oxime esters of ketoximes and aldoximes in high yields (90-97%) is reported. The reactions were performed using N- [3-(methylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDCI) reagent in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst at room temperature. The isolation and purification of products is very simple and in cases where product is solid, column chromatography is avoided.

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Synthesis of Oxime Esters and Ethers as Potential Psychotropic Agents

Cited by 15 publications

References 6 publications

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

Oximes: Novel Therapeutics with Anticancer and Anti-Inflammatory Potential

Synthesis of novel phthalimido oxime pseudoesters and evaluation of their cytotoxicity

A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

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