A. N. Lobov

Synthesis and neuropharmacological activity of N -1-adamantylcytisine-12-carbamide and its 12-thiocarbonyl analog

The neuropharmacological activity of two (–)-cytisine derivatives with adamantyl fragments was studied. It was shown that N-1-adamantylcytisine-12-thiocarbamide exhibited in tests in vivo a pronounced mnestic effect, increased the lifespan of laboratory animals under hypoxic conditions, and also enhanced in vitro binding of transcription factors NFAT and NF-κB to the DNA sequences corresponding to them.

Synthesis and specific nootropic activity of (–)-cytisine derivatives with carbamide and thiocarbamide moieties in their structure

N-(methylcytisinyl)-N′-substituted ureas, N-substituted cytisine-12-carbamides, and cytisine-12-thiocarbamide were prepared by reaction of (–)-cytisine with urea and thiourea and of (–)-cytisine and its 12-N-methyl-3-amino derivative with isocyanates. Their specific nootropic activity was studied in vivo. The therapeutic index was determined for the lead compound. Promising candidates for further pharmacological testing were found.

Reaction of ethyl acetoacetate with formaldehyde and primary amines

The condensation of ethyl acetoacetate with formaldehyde and primary amines in methanol at 65°C (Mannich reaction) gave up to 92% of hexahydropyrimidine derivatives containing ester and acetyl groups. Analogous reaction with aminopyridines stopped at the stage of formation of linear condensation products.

Synthesis of 3- and 5-Amino Derivatives of Methylcytisine

Synthetic approaches to 3- and 5-amino derivatives of methylcytisine via its nitration with subsequent reduction and a four-step synthetic sequence of exhaustive bromination, regioselective debromination, nitration and one-pot catalytic reduction of the nitro group, and debromination were proposed.

Oxidation of ursolic acid by ozone

Oxidation of methyl esters of ursolic and 3-acetoxyursolic acids by ozone formed products with a 12-oxo11S,13R-oxetane moiety on ring C.

NEW 12-N--HYDROXYETHYLCYTISINE DERIVATIVES WITH POTENTIAL ANTIARRHYTHMIC ACTIVITY

12-N-β-Hydroxyethylcytisine derivatives containing Cl, Br, and nitro groups on the 2-pyridone core were synthesized. Their antiarrhythmic activity was studied in vivo.

Ozonolysis of cyclomusalenone and its derivatives

Joint ozonolysis of cyclomusalenone O-methylketoxime and methyltrifluoromethylketone formed stereoisomeric triterpene 1,2,4-trioxolanes and N-methoxylactam. The structure of (24S)-24-methyl-29nor-cycloart-3,25-dione, which was obtained from ozonolysis of cyclomusalenone, was established by an x-ray crystal structure analysis.

Aza-Michael reaction of 12-N-carboxamide of (–)-cytisine under high pressure conditions

The first example of aza-Michael reaction of 12-N-carboxamide of quinolizidine alkaloid (–)-cytisine with α,β-unsaturated ketones, dimethyl acetylenedicarboxylate and β-nitrostyrene under high pressure condition has been described. It has been shown that the [4+2]-cycloaddition takes place in the case with N-phenylmaleimide.

SEARCH FOR COMPOUNDS WITH ANTIVIRAL ACTIVITY AMONG SYNTHETIC ()-CYTISINE DERIVATIVES

The antiviral activity of several amides and thio- and carboxamides of (-)-cytisine in addition to bromination and nitration products of its 2-pyridone core was studied. Compounds with a selectivity index close to 10 were found.

Molecular structure of 1,2,6,6,10,16,17-heptamethyl-20-(acetoxymethyl)pentacyclo [12.8.0.02.11.05.10.015.20]docos-17-en-7-yl acetate

The molecular structure of 3β,28-diacetoxy-18αH,19βH-ursan-20-en is determined. Compound C34H54O4 II crystallizes in the P212121 chiral space group: a = 8.2721(6) Å, b = 11.2728(8) Å, c = 32.559(2) Å.