504434-04-2Relevant academic research and scientific papers
AMIDE COUPLING PROCESS
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Page/Page column 13; 19, (2022/03/07)
The present invention relates to a synthetic process for amide coupling between a trihaloketone and an electron poor nucleophile, amenable to large scale synthesis, in particular, through a catalytic process.
An Atom-Economical Method for the Formation of Amidopyrroles Exploiting the Self-Assembled Resorcinarene Capsule
De Rosa, Margherita,Gaeta, Carmine,La Manna, Pellegrino,Neri, Placido,Soriente, Annunziata,Talotta, Carmen
supporting information, (2020/04/02)
Here is reported the first example of an organocatalyzed coupling between pyrrole and isocyanates in a nanoconfined space. The hexameric resorcinarene capsule C is able to catalyze the direct coupling between isocyanates and pyrroles to give amidopyrroles
Palladium-catalyzed direct arylations of five-membered heteroarenes bearing N-monoalkylcarboxamide substituents
Laidaoui, Nouria,Roger, Julien,Miloudi, Abdellah,El Abed, Douniazad,Doucet, Henri
experimental part, p. 4373 - 4385 (2011/10/09)
The palladium-catalyzed direct arylation of furan, thiophene, pyrrole, or pyrazole derivatives bearing CONHR substituents on C2, C3, or C5 with aryl bromides was studied. The use of KOAc as the base, DMAc as the solvent, and PdCl(C3H5)(dppb) as the catalyst was found to give regioselectively and without decarbamoylation the arylated heteroaromatics. Under these conditions, the amide substituent on the heteroaromatic does not act as a directing group. A wide range of functional groups such as acetyl, formyl, ester, nitrile, trifluoromethyl, and fluoro on the aryl bromide is tolerated. The palladium-catalyzed direct arylation of furan, thiophene, pyrrole, or pyrazole derivatives bearing CONHR substituents on C2, C3, or C5 with aryl bromides was studied. The use of KOAc as the base, DMAc as the solvent, and PdCl(C3H5)(dppb) as the catalyst was found to give regioselectively the arylated heteroaromatics.
Simple, potent, and selective pyrrole inhibitors of monoamine oxidase types A and B
Silvestri, Romano,La Regina, Giuseppe,De Martino, Gabriella,Artico, Marino,Befani, Olivia,Palumbo, Marianna,Agostinelli, Enzo,Turini, Paola
, p. 917 - 920 (2007/10/03)
N-Benzyl- and N-propargyl-1H-pyrrole-2-carboxyamides and some related methylenamines were synthesized and tested for their monoamine oxidase types A and B inhibitory activity. 2-(N-Methyl-N-propargylaminomethyl)-1H-pyrrole (24) was the most potent MAO-A inhibitor of the series [Ki(MAO-A) = 0.0054 μM], but it was not selective. Inhibitors N-4-fluorobenzyl-1H-pyrrole-2-carboxamide (12) and N-cyclohexylmethyl-1H-pyrrole-2-carboxamide (25) showed the highest MAO-A selectivity indexes (SI) corresponding to 2025 and > 2500, respectively, while 2-(N-methyl-N-benzylaminomethyl)-1H-pyrrole (21) was the most selective MAO-B inhibitor, having an SI of 0.0057.
Piperazinylalkyl Heterocycles as Potential Antipsychotic Agents
Scott, Malcolm K.,Baxter, Ellen W.,Bennett, Debra J.,Boyd, Robert E.,Blum, Paul S.,et al.
, p. 4198 - 4210 (2007/10/03)
We recently reported on a series of pyrrole Mannich bases orally active in inhibiting the conditioned avoidance response (CAR) in rats.These compounds exhibit affinity for both D2 and 5-HT1A receptors, and some are noncataleptogenic.Such a profile suggest that they may be potential antipsychotic agents which lack the propensity for causing extrapyramidal side effects and tardive dyskinesias in humans.One of these compounds, 1--1-piperazinyl>methyl>-1H-pyrrol-2-yl>methyl>-2-piperidinone (RWJ 25730, 1), was chosen for further development but found to be unstable in dilute acid.In order to improve stability, we replaced the pyrrole methylene linkage to the piperazine ring with ethylene, employed ethylene and dicarbonyl as linkers between the lactam and the pyrrole ring, placed electron-withdrawing groups on the pyrrole ring, and substituted acyclic amide for lactam.In addition, we replaced the pyrrole segment with other heterocycles including thiophene, furan, isoxazole, isoxazoline, and pyridine.Generally, replacemcent of the N-methylpyrrole segment with thiophene, furan, isoxazoline, or pyridine afforded compounds equipotent with 1 in CAR, which were more stable in dilute acid.In the case of side chain or lactam modifications, CAR activity was significantly decreased or abolished, with the exception of 6.For the most part, the modifications to 1 resulted in the decrease or loss of D2 receptor binding.However, within this series, 5-HT1A receptor binding was greatly increased, with thiophene 40 exhibiting an IC50 of 0.07 nM.The CAR activities of pyrroles 6 and 12, thiophene 40, furans 44-47, isoxazolines 49 and 50, pyridine 54 coupled with their weak or nonexistent D2 binding and strong 5-HT1A binding suggest that they may be acting via a nondopaminergic mechanism or that dopaminergic active metabolites are responsible.Pyrrole 6 and furans 44 and 47 show promise as antipsychotic agents based on their CAR activity, receptor-binding profile, and solution stability.
