CS218446B3 - Azachalcones derived from the isovanilfine derivative and a process for their preparation - Google Patents

Abstract

The invention relates to azachalcones derived from isovanillin of the general formula (t) where R is 3- or 4-pyridyl, and a method for preparing these compounds, consisting in the reaction of 3-(2:-diethylaminoethoxy)-4-methoxybenzaldehyde with methyl-3- or methyl-4-pyridyl ketone. The final compounds serve as starting materials for a number of more complex structures, their use is expected in the field of biologically active substances.

Description

The present invention relates to azachalcones derived from isovanillin of formula (t) wherein R is 3- or 4-pyridyl, and a process for the preparation of these compounds, comprising reacting 3- (2: -diethylaminoethoxy) -4-methoxybenzaldehyde with methyl-3- or methyl -4-pyridylketone. The final compounds serve as starting materials for a number of more complex structures and are expected to be used in the field of biologically active substances.

The invention relates to azachalcones of the formula I

R-CO-CH - ^^ _{Y-O-CH3-O-CH-N} (C ₂ H _s) (I) wherein R represents a 3- or 4-pyridyl. Antimicrobial, antihistamine and vasodilatory effects have been reported with known structurally related compounds. These compounds are most commonly prepared by the Claisen-Schmidt condensation of aromatic aldehydes with ketones using a basic catalyst (KOH, NaOH). diethylaminoethoxy) -4-methoxybenzaldehyde with methyl-3- or methyl-4-pyridyl ketone in ethanol solution at the boiling point of the solvent for several hours using piperidine as a catalyst The optimum reaction time is determined by ultraviolet spectra.

Illustrative of the compounds, process for their preparation, physical properties and biological effects are given by way of example.

Example 1

0.1 mol of 3- (2-diethylaminoethoxy) -4-methoxybenzaldehyde was dissolved in 10 ml of anhydrous ethanol, 0.1 mol of methyl-3-pyridyl ketone and 0.1 mol of piperidine were added. The mixture is allowed to react at the boiling point of the solvent for 240 minutes. After completion of the reaction, the volatiles from the reaction mixture were evaporated. Chloride 3- (2-diethylaminoethoxy j -4-methoxy-3'-ázachalko Nu is a yellow crystalline prá4 check with mp 180-184 C ^Q (anhydrous ethanol). UV spectrum:

Λ _max 249 and 357 nm (ε = 13,800 and 20100).

IR spectra:

$ (C-H) trans 996 CH11, 1667 cm @ -1;

H (cc) 1609 and 1582 cm ^-1 .

Indicative acute toxicity ranges from 200 to 400 mg per kg (subcutaneously in white mice), the Staphylococcus aureus inhibitory zone is 7.4 mm (diffuse dough, 1% roizt-ok, standard 5 mm diameter rollers), one minute decreases the in vivo heart rate in rats at 5 mg per kg to 64%, increases the lethal in vivo diffusion consumption of BaClz in rats, in vitro on isolated guinea pigs reduces heart rate at 10 μ% per ml to 79% and at 79% increased Ca ²⁺ ion concentration (8 µg per ml) to 85 ° / o. Example 2

The procedure is the same as in Example 1, the starting compounds being 3- (2-diethylaminoethoxy) -4-methoxybenzaldehyde and methyl-4-pyridyl ketone, the reaction time is 120 minutes. 3- (2-Diethylaminoethoxy) -4-methoxy-4'-azachalkone citrate forms yellow needle crystals, mp 191.5-193 ° C (anhydrous methanol).

UV spectra:

Λ _max 239 and 364 nm (ε = 12,500 and 18,500). IR spectra:

<5 (C-H) trans 096 Clil 1

H (c = o) 1656 cm @ -1 (c = c) 1588 cm @ -1;

H (c-o-o 1267 cm @ -1).

Claims (2)

Claims 1. Azachalcones derived from iso- derivatives wherein R represents 3- or 4-pyridyl. vanillin of formula I, 2. A process for the preparation of azachalcones according to claim 1, wherein R is as defined above, characterized in that R-CO-CH = CH- (O) -O-CHa to react 3- (2-diethylaminoethoxy) -4-methoxylbenzaldehyde with methyl-3- or methyl-3-methyl-4-methyl pyridyl ketone in ethanol solution CHjCn-O-N (P ^s of the solvent boiling temperature for 120.. 240 minutes using piperidine as Καί 'of the catalyst.