CS221037B1 - N, N‘-Dioxides of 1,3-bis (dimethylamino) -2-propyl esters of alkanecarboxylic acids and processes for their preparation - Google Patents

N, N‘-Dioxides of 1,3-bis (dimethylamino) -2-propyl esters of alkanecarboxylic acids and processes for their preparation Download PDF

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CS221037B1
CS221037B1 CS50382A CS50382A CS221037B1 CS 221037 B1 CS221037 B1 CS 221037B1 CS 50382 A CS50382 A CS 50382A CS 50382 A CS50382 A CS 50382A CS 221037 B1 CS221037 B1 CS 221037B1
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Czechoslovakia
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dimethylamino
bis
dioxides
preparation
propyl esters
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CS50382A
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Czech (cs)
Slovak (sk)
Inventor
Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Iveta Brtkova
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Ferdinand Devinsky
Ivan Lacko
Ludovit Krasnec
Iveta Brtkova
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Application filed by Ferdinand Devinsky, Ivan Lacko, Ludovit Krasnec, Iveta Brtkova filed Critical Ferdinand Devinsky
Priority to CS50382A priority Critical patent/CS221037B1/en
Publication of CS221037B1 publication Critical patent/CS221037B1/en

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Abstract

Vynález sa týká N,N‘-dioxidov l,3-bis(di- metylamino)-2-,propylesterov alkánkarboxy- lových kyselin všeobecného vzorca CHS x o R-C-O-CH g}» * I cw3 kde R značí lineárny alkylový reťazec s počtom atómov uhlíka 7 až 17 a spósobu ich přípravy; oxidáciou l,3-bis(dimetylami- no)-2-propylesterov alkánkarboxylových kyselin vodným roztokom peroxidu vodíka. Finálně zlúčeniny vykazujú antimikro- biálny účinok ako i povrchovoaktívne vlastnosti.The invention relates to N,N'-dioxides of 1,3-bis(dimethylamino)-2-propyl esters of alkanecarboxylic acids of the general formula CHS x o R-C-O-CH g}» * I cw3 where R denotes a linear alkyl chain with a number of carbon atoms of 7 to 17 and a method of their preparation; by oxidation of 1,3-bis(dimethylamino)-2-propyl esters of alkanecarboxylic acids with an aqueous solution of hydrogen peroxide. The final compounds exhibit antimicrobial activity as well as surface-active properties.

Description

Vynález sa týka N,N‘-dioxidov 1,3-bis (dimetylamino)-2-propylesterov alkánkarbo-xylových kyselín všeobecného vzorca

kde R značí lineárny alkylový reťazec s počtom atómov uhlíka 7 až 17 a spôsobu ich prípravy.

Je známe, že nearomatické amínoxidy obsahujúce vo svojej molekule najmenej jeden dlhý alkylový reťazec patria medzi biologicky účinné zlúčeniny s dobrými povr-chovoaktívnymi vlastnosťami a biodegra-dačnými schopnosťami.

Literatúra opisuje aj niektoré amínoxidy odvodené od ω-dialkylaminoalkylesterov al-kánkarboxylových kyselín, kde má spojovací reťazec dĺžku 2 až 3 atómy uhlíka, jedná’sa však všetko o monoamínoxidy. Tieto zlúčeniny vykazujú dobré povrchovoaktív-ne vlastnosti.

Zlúčeniny, ktoré sú predmetom vynálezu, doteraz ešte pripravené neboli, sú to látky nové, v chemickej literatúre neopísané, u ktorých sme zistili doteraz neznáme účinky na mikroorganizmy. V príkladoch sú uvedené vybrané zlúčeniny, ktoré sú predmetom vynálezu, spôsob ich prípravy ako aj ich charakterizácia spolu s uvedením ich antimikrobiálnej účinnosti (udanej ako minimálna inhibičná koncentrácia MIC v ^tg/ml voči Staphylococcus aureus a Esche-richia coli). Přikladl 0,05 M 1,3-bis (dimetylamino)-2-propyles-teru kyseliny dekánovej rozpustenej v 40 mililitroch izopropylalkoholu sa pridá 0,25 M 20—30 %' vodného roztoku peroxidu vodíka. Reakčná zmes sa zahreje na 40 až 60 °C a mieša sa potrebný čas. Po ochladení sa pridá platinová čerň a po rozložení prebytočného peroxidu vodíka sa rozpúšťadlo a voda oddestilujú a produkt sa vysuší. Po kryštalizácii zo suchého acetónu vzniká Ν,Ν'-dioxid 1,3-bis (dimetylamino)-2-propyl-esteru kyseliny dekánovej s t. t. 40—43 °C; Rf — 0,64 [sústava acetón : IN HC1 (1:1), detekcia Dragendorfovým činidlom v Mu-niérovej modifikácii; nosič silikagél); výťažok 70 % teórie. iC-spektrálne charakteristiky: vc-o 1692, Vc-o-c 1179, i>n-q ®64 (v cm’1, nujól, KBr). MIC: 700, 500). Príklad 2

Pracovný postup je ten istý ako v príklade 1 s tým rozdielom, že do reakcie sa použil 1,3-bis (dimetylamino )-2-propylester kyseliny hexadekánovej. Produkt N,N‘-di-oxid 1,3-bis (dimetylamino )-2-propylesteru kyseliny hexadekánovej mal it. t. 59—60 °C; Rf =? 0,29; výťažok 64 % teórie. IČ-spek-trálne charakteristiky: vc_0 1707, vc-o-c 1179, vn-o 936. MIC: 900,700.

The invention relates to N, N'-dioxides of 1,3-bis (dimethylamino) -2-propyl esters of alkanecarboxylic acids of the general formula

wherein R represents a linear alkyl chain having a carbon number of 7 to 17 and a process for preparing the same.

It is known that non-aromatic amine oxides containing at least one long alkyl chain in their molecule are biologically active compounds with good surface-active properties and biodegradation capabilities.

The literature also describes some amine oxides derived from ω-dialkylaminoalkyl esters of alkanoic acids, wherein the linking chain has 2 to 3 carbon atoms, but all are monoamine oxides. These compounds exhibit good surface-active properties.

The compounds of the present invention have not yet been prepared, they are novel, not described in the chemical literature, and have not yet been known to have an effect on microorganisms. In the examples, selected compounds of the invention, their method of preparation and their characterization are listed together with their antimicrobial efficacy (given as the minimum MIC inhibitory concentration in µg / ml against Staphylococcus aureus and Escherichia coli). EXAMPLE 1 0.05 M 1,3-bis (dimethylamino) -2-propyl esters of decanoic acid dissolved in 40 ml of isopropyl alcohol is added with 0.25 M of 20-30% aqueous hydrogen peroxide solution. The reaction mixture is heated to 40-60 ° C and the necessary time is stirred. After cooling, platinum black is added, and after the excess hydrogen peroxide has been decomposed, the solvent and water are distilled off and the product is dried. After crystallization from dry acetone, 1,3-bis (dimethylamino) -2-propyl ester of decanoic acid Ν, Ν-dioxide is obtained with mp 40-43 ° C; Rf = 0.64 [acetone: 1 HCl (1: 1) system, detection by Dragendorf reagent in Mueller modification; carrier silica gel); yield 70% of theory. iC-spectral characteristics: vc-o 1692, vc-oc 1179, i nq ®64 (in cm -1, nujol, KBr). MIC: 700, 500). Example 2

The working procedure is the same as in Example 1 except that 1,3-bis (dimethylamino) -2-propyl hexadecanoate is used in the reaction. The product N, N'-di-hexadecanoic acid 1,3-bis (dimethylamino) -2-propyl ester was obtained. mp 59-60 ° C; Rf =? 0.29; yield 64% of theory. IR-spectral characteristics: vc_0 1707, vc-oc 1179, vn-o 936. MIC: 900,700.

Claims (2)

PREDMET VYNALEZU 1. N,N‘-dioxidy l,3-bis{dimetylamino]-2--propylesterov alkánkarboxylových kyselin všeobecného vzorcaSUBJECT TO 1. N, N‘-dioxides of 1,3-bis (dimethylamino) -2-propyl esters of alkanecarboxylic acids of the general formula kde R značí lineárny alkylový reťazec obsahujúci 7 až 17 atómov uhlíka.wherein R represents a linear alkyl chain containing from 7 to 17 carbon atoms. 2. Spôsob prípravy zlúčenín všeobecného vzorca ako v bode 1, vyznačený tým, že sa nechá oxidovať l,3-bis(dimetylamino)-2--propylester alkánkarboxylovej kyseliny všeobecného vzorca2. A process for the preparation of compounds of formula (1), characterized in that 1,3-bis (dimethylamino) -2-propyl ester of alkanecarboxylic acid of the formula kde R má ten istý význam ako v bode 1, 20 až 30% vodným roztokom peroxidu vodíka pri teplotách 40 až 60 °C.wherein R is the same as in 1 with a 20 to 30% aqueous hydrogen peroxide solution at 40 to 60 ° C.
CS50382A 1982-01-25 1982-01-25 N, N‘-Dioxides of 1,3-bis (dimethylamino) -2-propyl esters of alkanecarboxylic acids and processes for their preparation CS221037B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109721511A (en) * 2019-01-21 2019-05-07 北京工商大学 A kind of preparation method of the Shuangzi amine oxide of the ethyl of ester group containing alkyl

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109721511A (en) * 2019-01-21 2019-05-07 北京工商大学 A kind of preparation method of the Shuangzi amine oxide of the ethyl of ester group containing alkyl

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