O. M. Glozman

The synthesis and antispasmodic activity of 4-phenylpyrrolidone-2-acetamides

It is well known [i] that the antispasmodic proPerty of various compounds frequently is connected with the presence of structural elements which include a phenyl radical or a benzene ring specifically oriented with respect to an amide group which, as a rule, is a fragment of an heterocyclic system (barbituric acid, hydantoin, pyrazolidindione, succinimide, etc.). Phenyl derivatives of pyrrolidone-2 satisfy these requirements, and, in fact, compounds possessing antispasmodic activity have been discovered among the derivatives of 5-phenylpyrrolidone-2 [2]. Therefore, it may be possible that a definite antispasmodic effect could be shown by derivatives of 4-phenylpyrrolidone-2, which, as indicated, are the most active of the phenylsubstitute 2-pyrrolidones in some other pharmacological properties [3]. It is also established that the introduction of substituents such as the acetamide group on the nitrogen atom of pyrrolidone-2 leads to the development of new types of pharmacological activity and to lower toxicity, such as the known preparation piracetam (2-pyrrolidinoacetamide) [4, 5].

Configuration of benzoylpyridineoximes studied by 1H and 13C NMR. Effect of protonation of the pyridine nitrogen atom

A simple and convenient method is proposed for determining the configuration of E,Z-isomers of 2-, 3-, and 4-benzoylpyridines. The difference in chemical shifts (δδ, ppm) in the system CCl4-DMSO-D6 and CCl4-DMSO-CF3COOD for the α-H atoms or the α, Β-C atoms of the pyridine ring can be used to determine the configuration. The shift (δδ) of the α-H signals to weak field is greater for the Z-isomers than for the E-isomers due to protonation of the pyridine nitrogen atom. The reverse dependence is seen in the 13C NMR for the E,Z-isomers. The signals of the α-C atoms shift to stronger field after protonation.

Synthesis and pharmacological activity of 3-(3-amino-2-oxypropoxy)pyridines

As a continuation of our search for new effective G-adrenal blocking agents of variable selectivity [2], we synthesized derivatives of l-aryl-3-aminopropanol-2 whose aryl segment is the 3-pyrydyl residue, and studied their pharmacological activity. The 2-(3-amino-2-oxypropoxy)pyridine series is known to include the S-adrenal blocker MK-761 which exhibits a vasedilatory effect [21]. As regards to the 3-(3-amino-2-oxypropoxy)pyridines (3-AOP), there has been practically no investigation of potential 8-adrenergic blockers (BAB) among these compounds.

Synthesis and pharmacological activity of 1-amino-3-(tetrahydro- and hexahydrodibenzofuran-8-iloxy-2)propanols

As a continuation of our research of new effective ~-adrenoblocking agents [i] and for the purpose of studying the effect that dibenzofuran ring saturation and the nature of the amine residue in the aminopropanol group has on ~-adrenoblocking activity, we synthesized derivatives of l-amino-3-(l,2,3,4-tetrahydroand 1,2,3,4,4a,9b-hexahydrodibenzofuran-8-iioxy)2-propanols (Ia-c, e-k, and IIa-d). We also thought it would be of interest to study simultaneously the effect of the indicated structural factors in compounds I and II on hypotensive, spasmolytic, broncholytic, and neurotropic activity.

Reactions and mass-spectrometric study of aza analogs of 2-aminochromone

Electrophilic substitution reactions at the C and N(2) atoms of 2-amino-4-oxo-4H-pyrano[2,3-b]pyridine were studied, 2-Aminoazachromones were subjected to a massspectroscopic study in comparison with 2-aminochromenes, and fundamental differences in their fragmentation were established.