II. Über die Einwirkung von Phosphoroxychlorid auf Methyl‐ (Äthyl‐) acetanilid. Synthesen von γ‐Chlorisochinocyaninen

Fischer, Otto; Müller, A.; Vilsmeier, Anton

doi:10.1002/prac.19251090104

Cited by 35 publications

(13 citation statements)

References 3 publications

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“…The drying agent was removed by filtration and the solvent was removed under reduced pressure to afford pure product in 95% yield as an orange solid. 12 …”

Section: Methodsmentioning

confidence: 99%

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Structure–Activity Relationships of Cyanoquinolines with Corrector–Potentiator Activity in ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Protein

et al. 2012

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Cystic fibrosis (CF) is caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. The most common CF-causing mutation, ΔF508-CFTR, produces CFTR loss-of-function by impairing its cellular targeting to the plasma membrane and its chloride channel gating. We recently identified, cyanoquinolines with both corrector (“Co”; normalizing ΔF508-CFTR targeting) and potentiator (“Po”; normalizing ΔF508-CFTR channel gating) activities. Here, we synthesized and characterized twenty-four targeted cyanoquinoline analogues to elucidate the conformational requirements for corrector and potentiator activities. Compounds with potentiator-only, corrector-only and dual potentiator-corrector activities were found. Molecular modeling studies (conformational search ⇒ force-field lowest energy assessment ⇒ geometry optimization] suggest that (1) a flexible tether and (2) a relatively short bridge between the cyanoquinoline and aryl amide moieties are important cyanoquinoline-based CoPo features. Further, these CoPo’s should adopt two distinct π-stacking conformations to elicit corrector and potentiator activities.

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“…The drying agent was removed by filtration and the solvent was removed under reduced pressure to afford pure product in 95% yield as an orange solid. 12 …”

Section: Methodsmentioning

confidence: 99%

“…Acylation of 6 with acetic anhydride gave 7 in near quantitative yield and subsequent Vilsmeier-Haack 12 type reaction gave chloroquinoline carboxaldehyde 8 . Neutralization, filtration and drying produced pure 8 in 95 % yield.…”

Section: Chemistrymentioning

confidence: 99%

Structure–Activity Relationships of Cyanoquinolines with Corrector–Potentiator Activity in ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Protein

et al. 2012

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“…Reaction of the 3,3-disubstituted 3H-indole, (1), with the Vilsmeier reagent (dimethylformamide and POCl 3 ) (Cheng et al, 1999(Cheng et al, , 2002Fischer et al, 1925;Jutz, 1976;Vilsmeier & Haack, 1927) gave compound (2), the product of N-formylation (Fritz, 1959). Further reaction of (2) with the Vilsmeier reagent and subsequent alkaline hydrolysis produced compound (4) (Fritz, 1959).…”

Section: Commentmentioning

confidence: 99%

Formylation of an indolenine: 2-(diformylmethylidene)-3,3-dimethyl-2,3-dihydro-1H-indole

et al. 2006

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“…In 1925 Fischer, Müller, and Vilsmeier published a paper describing the reaction between phosphoryl chloride and N ‐methylacetanilide, giving a number of products, including the quinolinium salt 1 and the salt 2 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of New Heterocycles Using 2‐(4‐Chloro‐1,3‐dihydro‐3,3,7‐trimethyl‐2H‐indol‐2‐ylidene) Propanedial

Alyari

Baradarani

Afghan

et al. 2013

Journal of Heterocyclic Chem

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4‐Chloro‐2,3,3,7‐tetramethyl‐3H‐indole (an indolenine) was produced by the reaction of 5‐chloro‐2‐methylphenylhydrazine hydrochloride with 3‐methylbutan‐2‐one via Fischer reaction. Exposure of the indolenine to the Vilsmeier reagent at 50°C produced a β‐diformyl compound, 2‐(4‐chloro‐1,3‐dihydro‐3,3,7‐trimethyl‐2H‐indol‐2‐ylidene)propanedial. This dialdehyde was reacted with arylhydrazines, acetamidinium chloride, urea, thiourea, guanidinium chloride, and cyanoacetamide to give various 5‐membered and 6‐membered heterocyclic products, each carrying a 4‐chloro‐3,3,7‐trimethyl‐3H‐indol‐2‐yl unit as a substituent, in excellent yields.

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II. Über die Einwirkung von Phosphoroxychlorid auf Methyl‐ (Äthyl‐) acetanilid. Synthesen von γ‐Chlorisochinocyaninen

Cited by 35 publications

References 3 publications

Structure–Activity Relationships of Cyanoquinolines with Corrector–Potentiator Activity in ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Protein

Structure–Activity Relationships of Cyanoquinolines with Corrector–Potentiator Activity in ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Protein

Formylation of an indolenine: 2-(diformylmethylidene)-3,3-dimethyl-2,3-dihydro-1H-indole

The Synthesis of New Heterocycles Using 2‐(4‐Chloro‐1,3‐dihydro‐3,3,7‐trimethyl‐2H‐indol‐2‐ylidene) Propanedial

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