Refernces
10.1002/jps.2600750621
The research describes a facile synthesis method for glycol metabolites of phenethylamine drugs, including potential metabolites of psynephrine, epinephrine, octopamine, and normacromerine. The purpose of this study was to develop a general synthetic scheme that yields high quantities of these metabolites using readily available monosubstituted and disubstituted acetophenones, overcoming challenges such as dimerization and pinacol-pinacolone rearrangement inherent in aromatic glycol synthesis. The process involved alpha-bromination, displacement with acetate ion, and reduction with lithium aluminum hydride, resulting in yields ranging from 46 to 91%.
10.1016/j.bmcl.2009.04.125
The research aimed to develop new selective COX-2 inhibitors to treat inflammation and inflammation-associated disorders with reduced gastrointestinal toxicities compared to traditional NSAIDs. The study focused on synthesizing a new group of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives with a methylsulfonyl pharmacophore and evaluating their COX-2 inhibitory activity. Key chemicals used in the synthesis included amines (such as benzylamine, phenethylamine, and cyclohexylamine), 4-methylthiobenzaldehyde, and thioglycolic acid. The most potent and selective COX-2 inhibitor identified was 3-benzyl-2-(4-methylsulfonylphenyl)-1,3-thiazinan-4-one (11a), with an IC50 of 0.06 μM and a selectivity index of 285.8. Molecular modeling suggested that the compound's potent and selective inhibitory activity was due to its specific interactions with the COX-2 active site. The study concluded that these derivatives could serve as promising candidates for the development of new anti-inflammatory drugs with fewer gastrointestinal side effects.
10.1016/S0040-4039(01)91108-6
The study investigates the anodic intramolecular arylation of enaminones to produce isoquinolines and benzazepines. Enaminones, which are prepared by condensation of various benzylamines, phenethylamines, and anilines with 1,3-diketones, serve as the key substrates. The anodic oxidation potentials of these enaminones are measured and listed in Table 1. The preparative electrolyses of enaminones 1, 3 - 5 lead to the formation of isoquinolines and benzazepines in fair yields, as shown in Table 2. The anode potentials for these reactions range from +0.8 to +1.6 V vs. s.c.e. The study also notes that enaminone k does not cyclize under the given conditions but forms the iminoquinone ketal 11 instead. The anode reaction described provides a convenient one-step preparation of isoquinolines and benzazepines, which are suitable intermediates for the synthesis of various alkaloids such as lycorane, Cephalotaxus, and erythrina alkaloids.
10.1021/jacs.6b07230
The study focuses on using ynamides as novel racemization-free coupling reagents for amide and peptide synthesis under mild conditions. It introduces a two-step, one-pot synthetic strategy where ynamides facilitate the hydroacyloxylation of carboxylic acids followed by aminolysis, enabling efficient amide bond formation without the need for protecting functional groups like -OH, -SH, and ArNH2. The methodology highlights the advantages of ynamides in avoiding racemization, especially in peptide coupling, demonstrating excellent selectivity and broad applicability for various carboxylic acids and amines. The study shows potential for scaling up peptide synthesis, with applications in pharmaceutical and industrial processes.
10.1021/acs.orglett.6b01171
The study presents a highly chemoselective palladium-catalyzed intramolecular C?H aminocarbonylation of Br-functionalized phenethylamines to synthesize six-membered benzolactams with good to high yields. The process involves the use of carbon monoxide (CO) and a palladium-based catalytic system, which includes Pd(TFA)2, BINOL, and Ag3PO4. These chemicals serve to facilitate the selective cyclization of phenethylamines via C?H functionalization, leaving the C?Br bond intact for further functionalization through various palladium-catalyzed coupling reactions. The study demonstrates the versatility of the method by successfully synthesizing a range of benzolactams with different substituents and further functionalizing the remaining C?Br bond in the cyclized products.
10.1021/jm00388a007
The research focuses on the synthesis and evaluation of a series of (3-phenylflavonoxy)propanolamines, with the aim of identifying potential antihypertensive agents that do not exhibit β-adrenergic receptor blocking activity. The study was motivated by the desire to develop a class of agents with both β-adrenoceptor antagonist and vasodilatory properties, potentially offering more effective treatment for hypertension. The researchers synthesized various compounds and tested them for their ability to lower systolic blood pressure in spontaneously hypertensive rats and for their affinity to β-adrenergic receptors. The conclusion was that some compounds in the series, particularly those with an n-propyl or cyclopropyl substitution, showed effective antihypertensive properties without antagonizing β-adrenergic receptors. The chemicals used in the synthesis process included benzylamine, formaldehyde, benzaldehyde, 2-phenethylamine, and various substituted amines, among others. The study highlighted the unique structure-activity relationships of these compounds, which, despite their structural similarities to classical β-blockers, did not exhibit β-antagonist properties but were still effective as antihypertensive agents.
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![Phenethyl-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-amine](/Databaselist/images/loading.webp)
