E. E. Mikhlina

Synthesis of 4-aminoquinuclidine and its derivatives

Two methods for preparing 4-aminoquinuclidine from quinuclidine-4-carboxylic acid have been developed. Acyl and alkyl derivatives of 4-aminoquinuclidine have been synthesized.

Synthesis and properties of (3-quinuclidyl)diarylcarbinols

The reaction of 3-ethoxycarbonyl-, 3-ethoxycarbonylmethyl-, and 3-benzoylquinuclidines with organometallic compounds was studied. General methods for the preparation of (3-quinuclidyl)-diarylcarbinols were developed, and the properties of these compounds were studied.

Synthesis and cholinolytic properties of esters of 3-hydroxyquinuclidine

The esters of 3-hydroxyquinuclidine with aliphatic, aliphatic--aromatic, and aromatic acids, which have been synthesized, display marked pharmacological activity the character of which is determined by the structure of the acylating residue. Esters of the lower aliphatic acids proved to have cholinomimetic action, esters of aromatic and aliphatic--aromatic acids are characterized by cholinolytic properties [i].

The synthesis of 1,2-diazabicyclo[3,3,1]nonane and 1,9-diazabicyclo-[4,3,0]nonane. iv

The new bicyclic systems 1,2-diazabicyclo[3,3,1]nonane and 1,9- diazabicyclo [4,3,0]nonane have been synthesized from 2- (and 3-) piperidineacetic acid via their nitroso-derivatives, and 3-oxo-1,2 diazabicyclo [3,3,1]nonane and 8-oxo-1,9-diazabicyclo[4,3, 0]nonane.

Effect of the character of ring fusion on the basicity of bicyclic hydrazides

The ionization constants of a number of 1,2-diazabicyclo-3-alkanones were measured. It was found that the basicity of 2-aza-3-quinuclidones is 1.5–2 orders of magnitude lower than in the remaining compounds. An assumption was made regarding the substantial effect of the character of ring fusion on the basicity of bicyclic hydrazides.

Di(2-thienyl)(3-quinuclidyl) carbinol (quiditene): An original antiulcerous drug of the quinuclidine series

Systematic investigations into the synthesis and characterization of quinuclidine compounds, conducted at the Center for Drug Chemistry (Moscow) [1-3], revealed a highly promising class of compounds-diaryl(3-quinuclidyl)carbinols. This class contains original agents capable of blocking Hi-histamine receptors, of which the antiallergic drug phencarol (I) is already used in practice and the drug bicarphen (II) has been approved for medicinal application [ 4 6].

Synthesis, structure, and properties, of 4a-hydroxyisoxazolidino[4,5-b]quinuclidines

Proton and carbon-13 NMR spectroscopy have been used to confirm the structure and establish the 4a,7a(RR/SS) configuration of 4a-hydroxyisoxazolidino[4,5-b]quinuclidines obtained by the reaction of N-arylhydroxylamines with 2-methylene-3-oxoquinuclidine. The reaction of this with hydroxylamine leads to a mixture of isomers of the oximes of 4a-hydroxyl-6-(3′-oxoquinuclidyl-2′)isoxazolidino[4,5-b]quinuclidine, each of which is formed as a single diastereomer.

Peculiarities of the mass-spectrometric fragmentation of (3-quinuclidinyl)diaryl(heteryl)carbinols

The principal pathways of the fragmentation of (3-quinuclidinyl)diaryl(heteryl)carbinols that involve cleavage of the quinudidine-carbinol C-C bond and the bridge bond in the quinuclidine ring containing the substituent were studied. In addition to the indicated fragmentation pathways, fragmentation proceeding with opening of the bridge bond of quinuclidine that does not contain a substituent is observed. The rearrangement of the molecular ion that precedes fragmentation via the indicated pathway is examined.

Synthesis and antitubercular activity of (4-pyridyl)glyoxylic acid

By adding in one portion, half of the calculated amount of pure VII and a double amount of 10% KOH to a 1% aqueous solution of KMnO~ warmed to 45~ and holding the mixture for i0 min at this temperature, up to 50% of the keto acid II can be obtained, based on the phenylhydrazone isolated from the reaction products, of about 20% based on the preparatively obtained keto acid II. The yield of the second oxidation product, nicotinic acid (VIII) is in this case about 40%. Compound VI under the same conditions undergoes a more extensive oxidation. The yield of V is 75%, while the keto acid I can be obtained in about 25% yield, based on the phenylhydrazone, or 5% based on the preparatively isolated keto acid I, containing about 20% (according to the PMR spectrum data) of other products.

Synthesis and pharmacological properties of 2- and 2,3-substituted quinuclidines

The catalytic reduction (in the presence of palladium on charcoal) of ~-~-unsaturated ketones Ia-c by a calculated quantity of hydrogen resulted in the formation of the corresponding 2-enzyland 2-furylmethyl-3-oxoquinuclidines (IIa-c). If compound Ia is further hydrogenated to the point where two equivalents of hydrogen are absorbed, the O-benzyl group in the original ketone IIa undergoes hydrogenolysis which leads to the formation of 2-(4-oxybenzyl) 3-oxoquinuclidine (IId).