Über lokalanästhetisch wirksame Substitutionsderivate des Diäthylamino‐acyl‐anilids

Büchi, J; Lauener, G N; Ragaz, L.; Böniger, Heinrich Rudolf; Lieberherr, R.

doi:10.1002/hlca.19510340131

Cited by 19 publications

(6 citation statements)

References 3 publications

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“…2-Iodoacetanilides 1 and pyrazoles 2 were prepared according to the literature. 7,8,18 Melting points were recorded with a Boetius apparatus. UV spectra (400-4000 nm) were obtained with a VSU-2P Zeiss-Jena Spectrophotometer, using MgO as a standard.…”

Section: Methodsmentioning

confidence: 99%

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

Zălaru¹,

Dumitraşcu²,

Drăghici³

et al. 2009

Arkivoc

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Section: Methodsmentioning

confidence: 99%

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

Zălaru¹,

Dumitraşcu²,

Drăghici³

et al. 2009

Arkivoc

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“…Both lidocaine and its analogs are known to be obtained by reaction of some 2-chloroacetanilides with amines. We have chosen another synthetic route since the 2-chloroacetanilides we obtained by the Löfgren and Büchi methods did not react with pyrazole or its derivatives [2,18]. We therefore converted the 2-chloroacetanilides into the more reactive 2-iodoacetanilides with sodium iodide in acetone under reflux (Scheme 1).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis, spectroscopic, and X-ray structural characterization of pharmacologically active substituted pyrazolyl-acetanilides

et al. 2009

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Five new pyrazole acetanilides were synthesized by N-alkylation of pyrazole and its derivatives with 4 0 -propionyl-2-iodoacetanilide. Compounds 1-5 were characterized by 1 H NMR, 13 C NMR, IR, UV-Vis, MS, and elemental analysis. X-ray structures of representative compounds 1, 3, and 5 established their conformations and solid-state hydrogen bonding preferences. Acute toxicity, local anesthetic, and antiarrhythmic activities were assessed for compounds 1-5 using established protocols. Lower potencies and lower acute toxicities were recorded relative to lidocaine. Enhanced anesthetic activity of compound 3 was attributed to the presence of the propionyl group in the molecule. Experimental Synthesis and characterizationAll compounds referred to in this article, namely the 4 0propionyl-2-chloroacetanilides, 4 0 -propionyl-2-iodoacetanilides, and the substituted pyrazoles, were prepared according to published methods [2,9,10].All melting points were recorded with a Boetius apparatus and are uncorrected. Electronic spectra within the 400-4000 nm range were obtained using a VSU-2P Zeiss-Jena Spectrophotometer, using MgO as a standard. IR spectra (KBr pellets) were measured on a BIO-RAD FTS-135 Spectrometer. NMR spectra were recorded on a Varian Gemini 300 Spectrometer operating at 300 MHz ( 1 H NMR) and 75 MHz ( 13 C NMR), respectively, in CDCl 3 or DMSO-d 6 . The chemical shifts were referred to tetramethylsilane (TMS) as the internal standard. GS-MS were recorded on a Varian Saturn 2000 GC/MS. The general procedure for the synthesis of pyrazoles 1-5 is given below with reference to compound 1. Spectroscopic data for 1-5 follow.2-(Pyrazol-1-yl)-4 0 -propionylacetanilide (1) About 4.0 g (1.26 mmol) 4 0 -propionyl-2-iodoacetanilide and 0.86 g (1.26 mmol) of pyrazole were dissolved in 3 mL of DMF to which an equimolar amount of sodium carbonate was then added. The reaction mixture was heated at 60°C for 5 h and was then treated with 10% sodium carbonate solution. The precipitate was filtered by suction and the product was recrystallized from isopropanol.2-(Pyrazol-1-yl)-4 0 -propionylacetanilide (1).

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“…Procedure. 23 To a stirred mixture of the arylmethylamine (1 mol), anhydrous (CH3)2CO (200 mL), and dry Na2C03 (2 mol) was added dropwise an excess of chloroacetyl chloride (2 mol). The reaction mixture was maintained at room temperature during 2 h. The very careful addition of H20 yielded the title derivative as a precipitate, which was filtered, washed (H20), and recrystallized twice.…”

Section: Lv-(chloroacetyl)arylmethylamines (Table Vii) Generalmentioning

confidence: 99%

“…Table VII) were prepared from the corresponding oximes by the usual method19 and a special synthesis described20 under Experimental Section. Compound 3a was prepared by alkaline fusion of fluorenone;21 the diphenyl-2-carboxylic acid obtained was treated as usual by S0C12 and NH4OH to give the corresponding amide, which was reduced by LiAlH4 in dry THE according to ref I) following Scheme II by a slight modification of the method of Büchi et al 23 The free bases 1-16 were converted into their hydrochlorides by treatment with etheral HC1, except those indicated in Table I.…”

mentioning

confidence: 99%

Quantitative structure-activity relationships for N-[(N',N'-disubstituted-amino)acetyl]arylamines for local anesthetic activity and acute toxicity

Heymans¹,

Therizien²,

Godfroid³

et al. 1980

J. Med. Chem.

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The synthesis and physicochemical properties of a series of N-[N',N'-disubstituted-amino)acetyl]arylamines are described. A QSAR method is applied to local anesthetic activity and acute toxicity by means of a "nonclassic" substituent variation involving a modification on both aryl and amino moieties. The choice of the different parameters (partition coefficient, pKa, connectivity index, molar refraction, and molar volume) is discussed and their different methods of determination are described. Molar refraction is the parameter which explains best the variance of the local anesthetic activity, and the quadratic regression with MR leads to a "posteriori" synthesis of one compound with optimized activity. However, the partition coefficient is the most explicative parameter for intravenous toxicity.

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Über lokalanästhetisch wirksame Substitutionsderivate des Diäthylamino‐acyl‐anilids

Cited by 19 publications

References 3 publications

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

Synthesis, spectroscopic, and X-ray structural characterization of pharmacologically active substituted pyrazolyl-acetanilides

Quantitative structure-activity relationships for N-[(N',N'-disubstituted-amino)acetyl]arylamines for local anesthetic activity and acute toxicity

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