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The hypoglycemic activity of glycyrrhizic acid (GA, I), its trisodium (II) and sodium-dilithium salts (III), and a conjugate with L-methionine methyl ester (IV) was studied using an alloxan diabetes model after peroral administration to male Wistar rats. It was found that GA and its conjugate IV at a dose of 100 mg/kg exhibited hypoglycemic activity and reduced the blood glucose content of the animals by 35.5 and 42.6%, respectively, after 120 min. GA conjugate IV had low toxicity and hypoglycemic activity superior to those of GA and acarbose.

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547.94:547.834.2 N. Z. Baibulatova, L. V. Spirikhin, M. S. Yunusov, N. S. Makara, N. Zh. Baschenko, and V. A. Dokichev Derivatives of N-(2-hydroxyethyl)cytisine, N-(2-hydroxypropyl)-, N-(2-hydroxy-2-(1-adamantyl)ethyl)-, and N-(2-hydroxy-2-phenylethyl)cytisine, were synthesized by reduction of N-(2-oxopropyl)-, N-(2-oxo-2-(1-adamantyl)ethyl)-and N-(2-oxo-2-phenylethyl)cytisine with metal hydrides. The antiarrhythmic and analgesic activities of the prepared compounds were investigated.Cytisine (1) and its derivatives are attractive to researchers owing to their broad spectrum of physiological activity (spasmolytic [1], insecticidal [2], cholinergic [3], analgesic [4]) and the ability to use them in catalytic reactions as optically active ligands [5]. We recently showed that N-(2-hydroxyethyl)cytisine has low toxicity and exhibits high antiarrhythmic activity compared with known antiarrhythmics [6,7].The goal of the present work was to synthesize new cytisine derivatives [8][9][10][11] and to study the structure-activity (antiarrhythmic) relationship for N-(2-hydroxyethyl)cytisine derivatives. Thus, we synthesized N-(2-hydroxypropyl)-(4a), N-(2-hydroxy-2-(1-adamantyl)ethyl)-(4b), and N-(2-hydroxy-2-phenylethyl)cytisine (4c) via reduction of the corresponding 2-alkyl-or 2-phenyl substituted N-(2-oxoethyl)cytisines 3a-c, which were prepared by reacting 1 and bromoketones 2a-c. R = Me (a), Ad (b), Ph (c)Ketones 3a-c were prepared by reacting 1 with bromoketones [bromoacetone (2a), 1-adamantyl-2-bromomethylketone (2b), bromoacetophenone (2c)] in anhydrous acetone in the presence of K 2 CO 3 for 1 h in 95-99% yields.The reduction of these ketones with NaBH 4 , LiAlH 4 , (i-Bu) 2 AlH, and AlH 3 ·N(Me) 3 was studied in order to investigate the effect of the optically active center of cytisine and the nature of the metal hydride on the new asymmetric center formed by conversion of the carbonyl in 3a-c into a secondary alcohol.

Some representatives of the class of sulfur-containing organic compounds, including derivatives of sulfones [1], dialkyldisulfides [2], and 3-thiabicyclohexanecarboxylic acid [3], were reported to possess anti-inflammatory activity. Biological activity is also inherent in 1,2,5-thiadiazole and its condensed derivatives, which act upon central nervous system and influence tissue metabolism [4].In continuation of our investigations into new bicyclic bis-sulfoxides, we have synthesized 4-methyl-1-(methylsulfinylmethyl)-7-thiabicyclo[3.3.1]non-3-en-2-one-7-oxide (I) and studied the anti-inflammatory and antiarrhythmic properties of this compound.The synthesis I was conducted according to the scheme depicted below. In the first step, we obtained 4-methyl-1-(methylthiomethyl)-7-thiabicyclo[3.3.1]non-3-en-2-one (II) via alkylthiomethylation of propanone with a mixture of formaldehyde, methylmercaptan, and sodium sulfide in an alkaline medium [5]. In the second step, compound II was oxidized in a 28 -30% aqueous hydrogen peroxide solution at 20°C, and the target compound I was obtained with a yield of 95%.The purity and the proposed structures of the synthesized compounds were confirmed by the results of elemental analyses and by the data of IR, 1 H NMR, and 13 C NMR spectroscopy (Tables 1 and 2). The IR spectra of compounds I and II exhibit absorption bands at 1656, 1618, 1624, and 1654 cm -1 characteristic of the stretching vibrations of the C=O and C=C bonds [6].In the 13 C NMR spectrum of compound I, the signals from carbon atoms C 6 (48.43 and 48.54 ppm), C 8 (56.75 and 56.06 ppm), C 11 (62.62 and 61.52 ppm), and C 13 (36.08 and 35.79 ppm) are shifted toward lower fields as compared to the analogous signals in the spectrum of compound II (Table 2). In addition, almost all signals in the 13 C NMR spectrum of compound I are doubled, which is indicative of the existence of two isomers. The spectra were assigned separately to each isomer. The appearance of a diastereomer pair is related to the presence of a chiral carbon atoms C 1 and a pyramidal sulfoxide sulfur atom in the aliphatic substituent, which make possible the formation of two d-diastereomers with R*R* and R*S* centers [7].The 1 H C NMR spectrum of compound I displays clearly distinguished signals due to the greater isomer and shows the signals from diastereotopic protons at C 11 in the form of two doublets with a geminal spin -spin coupling constant of 13.3 Hz and a relative chemical shift Dd = 0.61 ppm. For the second diastereomer, this difference is below 0.29 ppm. Based on the published data [7], the diastereomer with a greater difference of the chemical shifts is identified as the erythro isomer (Ia), while the component with a smaller Dd value is identified as the threo isomer (Ib). Both isomers are 659