T. Ya. Filipenko

Structure of the cationic forms of pyrimido [4,5-b][1,4]thiazines — A new type of folic acid antagonist

The protonation of 4-methoxy-, 4-amino-, and 4-dimethylamino-6-aminopyrimido[4,5-b][1,4]thiazines and N-(4-methoxy-5-pyrimidinyl)acetamidine was studied by 1H and 13C NMR spectroscopy. It is shown that the addition of a proton in the first three compounds takes place at the N5 atom of the thiazine ring, whereas in the case of N-(4-methoxy-5-pyrimidinyl) acetamidine primary protonation is observed at the nitrogen atom of the amidine group, and the second proton adds to the N1 atom of the pyrimidine ring.

Reaction of ethyl quininate derivatives with phenyllithium

The reactions of ethyl quininate and its 1-methyl-2-oxo derivative and ethyl 1-methyl-1,2,3,4-tetrahydroquininate with phenyllithium were investigated. The structures of the products were confirmed by IR, PMR, and mass-spectroscopic data.

Acetyl Derivatives of 3-Quinuclidone

Methods have been developed for the synthesis of mono- and bisacetyl derivatives of 2-hydroxyarylmethylene-3-quinuclidone oximes.

7-Aryl-4a-hydroxy-4a,6,7,7a-tetrahydroisoxazolo[4,5-b]quinuclidines as NO Donors

Abstract7-Aryl-4a-hydroxy-4a,6,7,7a-tetrahydroisoxazolo[4,5-b]quinuclidines have been prepared from 2-arylmethylene-3-quinuclidones and hydroxylamine and they are able to release NO upon mild oxidation with K3[Fe(CN6)] in basic medium.

Thiophene monolithiumization with phenyllithium as a key stage in the large-scale synthesis of Di(2-thienyl)(3-quinuclidyl)carbinol—The new potential antiulcerous drug quiditene

The results of extensive investigations devoted to the synthesis and properties of quinuclidine compounds, conducted at the Center for Drug Chemistry (Moscow) [ 1 5], showed that di(2-thienyl)(3-qninuclidyl)carbinol hydrochloride (It), a thiophene analog of the antiallergic drugs phencarol (Ia) and bicarphen (Ib), possesses pronounced antisecretor and antiulcerous activity [6]. The previous publication [7] reported on a method developed for the synthesis of compound Ic, called quiditene, proceeding from 2-thienyllithium (II) and 3-ethoxyearbonylquinuclidine (IV):

Search for long-actingβ-adrenoblockers among 4-hydroxyindole derivatives

In searches for long-acting/~-adrenoblockers, we have synthesized and studied some derivatives of 4-hydroxyindole-3acetic acid. It is known from the literature that the compound bopindolol (I; 4-(2-benzyloxy-3-tert-butylaminopropoxy)-2methylindole hydromalonate) has prolonged, fl-adrenoblocking activity [7]. Pindolol (4-(2-hydroxy-3-isopropylaminopropoxy)indole) is also among indole derivatives that are widely used in medicine; it, however, is short-acting. Due to the wide usage of fl-adrenoblockers in treating cardiovascucular diseases and the need for their long-term use, it is of great importance to create new compounds of this group that have long-acting fl-adrenoblocker activity. We first prepared a bopindolol analogue having, in contrast to the latter, a methyl group at position 3 of the indole nucleus (II). This compound was synthesized from the corresponding epoxide (III) by reaction with amine Va, which contains a protecting benzyl group on the nitrogen atom. The resulting hydroxyamine (Via) was benzoylated via the hydroxy group, and the benzyl group removed from resulting derivative VIIIa by hydrogenolysis. Compounds VIIIb and IX were obtained analogously.

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.

Search for β-adrenergic blockers among aminoxypropyl derivatives of 4-hydroxyindolyclacetic acid and 4-hydroxyskatole

Among the aminopropoxyl esters of 4-hydroxyindole are found highly effective

Purification of 3-ethoxycarbonylquinuclidine and its conversion to 3-quinuclidinecarboxylic acid and 3-quinuclidinylmethanol

-adrenergic blockers. The clearest representative of this group of substances is pindolol, displaying the characteristic featuers of action (high intravenous sympathomimetic activity) [6, 8]. The same group includes mepindolol [5] and bopindolol [4]. The latter acts longer than other

Catalytic reduction of 4-(3-oxoquinuclidyl-2-methylidene)-6-methoxyquinoline and its ethyleneketal

-adrenergic blockers [2, 3, 7]. Further search for active compounds within this series is of interest. This has become possible as a result of development of microbiological synthesis of 4-hydroxyindolylacetic acid [I]. At the same time, 4-hydroxyskatole has also become available, since it can be obtained by decarboxylation of the acid.