Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole

Cuevas-Yáñez, Erick; Serrano, João; Huerta, Gloria; Muchowski, Joseph M.; Cruz-Almanza, Raymundo

doi:10.1016/j.tet.2004.08.009

Cited by 44 publications

(18 citation statements)

References 36 publications

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“…The method for preparing the sulfonylhydrazone analogues was based on a condensation reaction from sulfonylhydrazide and an appropriate aldehyde (piperonal or vanillin) as shown in Fig. . Vanillin was commercially obtained.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease

Fernandes

Cunha

Sakata

et al. 2017

Archiv der Pharmazie

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Alzheimer's disease (AD) is the most common type of dementia and related to the degeneration of hippocampal cholinergic neurons, which dramatically affects cognitive ability. Acetylcholinesterase (AChE) inhibitors are employed as drugs for AD therapy. Three series of sulfonylhydrazone compounds were designed, and their ability to inhibit AChE was evaluated. Fifteen compounds were synthesized and twelve of them had IC values of 0.64-51.09 μM. The preliminary structure-activity relationships indicated that the methylcatechol moiety and arylsulfonyl substituents generated better compounds than both the benzodioxole and alkylsulfonyl chains. Molecular dynamics studies of compound 6d showed that the interaction with the peripheral binding site of AChE was similar to donepezil, which may explain its low IC (0.64 μM). Furthermore, the drug-likeness of 6d suggests that the compound may have appropriate oral absorption and brain penetration. Compound 6d also presented antiradical activity and was not cytotoxic to LL24 cells, suggesting that this compound might be considered safe. Our findings indicate that arylsulfonylhydrazones may be a promising scaffold for the design of new drug candidates for the treatment of AD.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease

Fernandes

Cunha

Sakata

et al. 2017

Archiv der Pharmazie

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“…Carbeninsertionen in die N‐H‐Bindung von Imidazolen und Benzimidazolen 5 und gewöhnlichen Aminen 7 sowie in die P‐H‐Bindung im Phosphinoxid 9 gelangen mit verschiedenen Kupferkatalysatoren (Schema ).…”

Section: Hydrazoneunclassified

Neue Ansätze für die Synthese von Metallcarbenen

Jia

2016

Angewandte Chemie

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Metallcarbene sind vielseitige Verbindungen, deren Reaktivität sowohl durch das Metall als auch den Liganden gesteuert werden kann. Zur Synthese von Metallcarbenen nutzt man im Allgemeinen die Stickstoff‐Eliminierung von Diazoverbindungen, die allerdings häufig instabil, explosiv und toxisch sind, was ihren Einsatz in großskaligen Synthesen einschränkt. Demzufolge gibt es eine intensive Suche nach nachhaltigen und ungefährlichen Ersatzsubstraten für die zuverlässige Herstellung von Metallcarbenen. In diesem Aufsatz fassen wir die wichtigsten Fortschritte bei der Erzeugung, katalytischen Reaktionen und der Selektivitätskontrolle von Metallcarbenen zusammen, die nicht aus Diazoverbindungen gebildet wurden.

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“…mediate which was subsequently reacted with various carbonyl compounds giving, after quenching with water, the corresponding products 16 ( Figure 2; Table 2, entries [16][17][18]. In this case, the reaction with a prochiral electrophile (i.e., acetophenone or pivalaldehyde) occurred with some diastereoselectivity.…”

Section: Scheme 1 Proposed Mechanism For the Isoprene-mediated Lithiamentioning

confidence: 99%

Isoprene as Lithiation Mediator: Synthesis of 2-Substituted 1-Alkylimidazole Derivatives

et al. 2012

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The lithiation of different imidazoles bearing a primary (i.e., butyl, pentyl, dodecyl) or secondary (i.e., cyclohexyl, 1-methylheptyl) alkyl substituent on the nitrogen has been successfully achieved by means of an isoprene-mediated protocol. The subsequent reaction of the 2-lithioimidazole intermediates with different electrophiles leads to the formation of interesting 1,2-disubstituted imidazoles.

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Copper carbenoid mediated N-alkylation of imidazoles and its use in a novel synthesis of bifonazole

Cited by 44 publications

References 36 publications

Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease

Synthesis, Molecular Modeling, and Evaluation of Novel Sulfonylhydrazones as Acetylcholinesterase Inhibitors for Alzheimer's Disease

Neue Ansätze für die Synthese von Metallcarbenen

Isoprene as Lithiation Mediator: Synthesis of 2-Substituted 1-Alkylimidazole Derivatives

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