[Stereochemistry of substituting the allyl hydroxyl group with fluorine atom in prostaglandins. Synthesis of 15-fluoro-11,15-dideoxyprostaglandins E1]. / Stereokhimiia zameny allil'noi gidroksil'noi gruppy na atom ftora v prostaglandinakh. Sintez 15-ftor-11,15-didezoksiprostaglandinov E1.

(+/-)-15-Fluoro-11,15-dideoxyprostaglandin E1 and its methyl and ethyl esters were synthesized. Dehydroxyfluorination reaction (+/-)-11-deoxyprostaglandin E1 esters with various reagents based on SF4 was studied. Along with the target 15-fluorides (mixtures of alpha- and beta-epimers), products of allylic shift and dehydration in a ratio dependent on the fluorination agent were shown to be formed. With a morpholinotrifluorosulfuran-tris(morpholine)sulfonium trimethyldifluorosilicate mixture, the maximal excess (70%) of one of the 15-fluoro epimers was achieved. Possible mechanisms of dehydroxyfluorination of (+/-)-11-deoxyprostaglandin E1 esters with dialkylaminoflluorosulfurans were proposed. Methyl esters of 15-alpha-fluoro- and 15-beta-fluoro-11,15-dideoxyprostaglandin E1 exhibited moderate antiaggregation activity in rabbit platelet tests.

[The effect of new synthetic prostanoids on the aggregation activity of human thrombocytes]. / Vliianie novykh sinteticheskikh prostanoidov na agregatsionnuiu aktivnost' trombotsitov cheloveka.

We found that a number of new synthetic prostanoids caused a prominent reduction of human platelet aggregation in the in vitro experiments. Moreover, two of this agents, IOS 3933 and IOS 4732, gives storage stability. Hemoxygenase activity, metabolic homeostasis of bilirubin in brain and transport function of serum albumin in animals receiving cobalt chloride.

[The effect of new synthetic prostanoids on the indices of the blood coagulation system]. / Vliianie novykh sinteticheskikh prostanoidov na nekotorye pokazateli svertyvaiushchei sistemy krovi.

In the experiments on rabbits it was shown, that the administration of prostanoids IOS 3933 caused a reduction of ADP- and collagen induced platelet aggregation, platelet adhesion to collagen and elevation of t-PA level. This prostanoid prevented both a decrease in platelet count and reduction of AT III activity, but did not affect the protein C level during thromboplastin infusion.

[Total synthesis and properties of prostaglandins. XXXVIII. Synthesis of 11-deoxyprostaglandin-E1 derivatives with amino acids and amines]. / Total'nyi sintez i svoistva prostaglandinov. XXXVIII. Sintez proizvodnykh 11-dezoksiprostaglandina-D1 s aminokislotami i aminami.

In order to study the physiological functions of 11-deoxyprostaglandin E1-alpha, a series of its amide derivatives with amino acids and some amines were synthesized using mixed anhydride technique. The myotropic properties of newly synthesized compounds were investigated.

[Total synthesis and properties of prostaglandins. XXXI. Synthesis of pyranylated and glycosidated omega-hydroxyalkyl ethers of 11- deoxyprostaglandin E1]. / Total'nyi sintez i svoistva prostaglandinov. XXXI. Sintez piranilirvannykh i glikozidirovannykh omega-gidroksialkilovykh éfirov 11-dezoksiprostaglandina E1.

Four methods of the synthesis of model glycosides with 11-deoxyprostaglandin E1 and a connecting polymethylene chain as the aglycone are compared. Interaction of potassium salt of prostaglandin PG with omega-iodoalkylglycosides is the most promising approach.

[A method for predicting the course of chronic myeloleukemia]. / Sposob prognozirovaniia techeniia khronicheskogo mieloleikoza.

The effects of a synthetic prostaglandin E1 (PGE1) analog on colony-forming activity in agar cultures of peripheral blood and bone marrow was studied in 28 patients with chronic myeloid leukemia and 9 hematologically healthy subjects. Addition of PGE1 to normal bone marrow culture was followed by a significant drop in the number of colonies per dish in 8 out of the 9 subjects. In leukemic patients, the effect was bizarre. It proved to be in correlation with survival thus suggesting that the effect of PGE1 on colony-forming activity of granulocyte-macrophage precursors be used in predicting survival in patients with chronic myeloid leukemia.

[Total synthesis and properties of prostaglandins. XXI. Synthesis of a 4,4-dimethyl-4-sil analog of 11-deoxyprostaglandin E1]. / Total'nyi sintez i svoistva prostaglandinov. XXI. Sintez 4,4-dimetil-4-sila-analoga 11-dezoksiprostaglandina E1.

Total synthesis of a new prostaglandin analogue, 11-deoxy-4,4-dimethyl-4-sil-prostaglandin E1, is carried out through synthesis of a silicon-containing alpha-chain precursor and a 2-substituted cyclopentenone derivative followed by their cuprate-induced interaction.

[Prostaglandin-like inhibitors of prostaglandin-H-synthase]. / Prostaglandinopodobnye ingibitory prostaglandin-H-sintazy.

The effect of none prostaglandin-like cyclopentanone derivatives on the prostaglandin H synthase activity was studied. Seven substances proved to be inhibitors of the enzyme, some of the being similar to the well-known nonsteroid antiinflammatory drugs with respect to their inhibitory activity.

[Effect of doprostone on fatty acid metabolism disturbances in the rat heart caused by adrenergic influences]. / Vliianie doprostona na vyzyvaemye adrenergicheskimi vozdeistviiami narusheniia metabolizma zhirnykh kislot v serdtse krys.

Administration of isoproterenol results in a marked increase (by 4.85 times) of the blood serum concentration of free fatty acids. In the heart there was found a four-fold increase of the concentration of long-chain acylcarnitine against the background of a reduction of free carnitine content. A preliminary administration of doprostone in a dose of 50 micrograms/kg intraperitoneally for 10 days completely prevents isoproterenol-induced increase of the serum concentration of free fatty acids and the heart concentration of long-chain acylcarnitine. Doprostone contributes also to preservation of the myocardium content of free carnitine under conditions of adrenergic influences. Correction of fatty acid metabolism under the influence of doprostone indicates the possibility of the heart protection against lesions caused by fatty acids and their detergent metabolites (long-chain acyl-CoA and acylcarnitine) during adrenergic and ischemic influences.

[Total synthesis and properties of prostaglandins. XXIV. Synthesis of glycerides with prostaglandin acyl residues]. / Total'nyi sintez i svoistva prostaglandinov. XXIV. Sintez glitseridov s prostaglandinovym atsil'nym ostatkom.

Synthesis of a number of model triglycerides and lysoglycerides bearing the acyl moieties of 11-deoxyprostaglandin E1, and palmitic acid residues has been carried out.

[Effect of synthetic prostaglandin E1 on the cardiac blood supply and systemic hemodynamics in acute myocardial ischemia]. / Vliianie sinteticheskogo prostaglandina E1 na krovosnabzhenie serdtsa i sistemnuiu gemodinamiku pri ostroi ishemii miokarda.

The effect of a native synthetic prostaglandin E1 on the blood supply and basic parameters of hemodynamics in acute myocardial ischemia induced by coronary artery occlusion was studied. It was found that the preparation in doses of 5 and 10 mg/kg increases the general and collateral coronary circulation by redistributing it into the endocardium of myocardial ischemic lesion. PGE1 increased the systolic discharge and the minute volume of the heart, enhanced the contractile myocardium activity. With an increase of the preparation dose its positive effect was not enhanced.

[Experimental research on the antisecretory and antiulcer activity of (+/-) 15 alpha-OH-11-deoxyprostaglandin E1]. / Eksperimental'noe issledovanie antisekretornoi i protivoiazvennoi aktivnosti (+/-) 15 al'fa-OH-11-dezoksiprostaglandina E1.

(+/-) 15 alpha-OH-11-deoxyprostaglandin E1 was found to possess a pronounced antisecretory activity at stimulation of gastric secretion in cats with pentagastrin. In rats the compound exerted the protective effect of cells of the gastric mucosa, especially on indomethacin and stress models of ulcerogenesis. The cytoprotective effect of the compound seemed to be related to its action on secretion of mucus as well as to its stimulation of zinc accumulation in cells that stabilized cell membranes and suppressed the secretory activity of mast cells.

[Total synthesis and properties of prostaglandins. XIV. Amide derivatives of 3alpha-tetrahydrofuranyloxy-5-hydroxyimino-2beta- (3alpha-tetrahydrofuranyloxy-trans-1-octenyl)-cyclopentane- 1alpha-acetic acid]. / Total'nyi sintez i svoistva prostaglandinov. XIV. Amidnye proizvodnye 3alpha-tetragidrofuraniloksi-5-gidroksiimino-2beta- (3alpha-tetragidrofuraniloksi-trans-1-oktenil)-tsiklopentan- 1alpha-uksusnoi kisloty.

Several novel prostaglandins containing an amide group in the alpha-chain have been prepared by the mixed carbonic anhydride method from 3 alpha-tetrahydrofuranyloxy-5-hydroxyimino-2 beta-(3 alpha- tetrahydrofuranyloxy-trans-1-octenyl)-cyclopentane-1 alpha-acetic acid and omega-amino acids with a linear chain of varying length (CH2-group number from 1 to 7). The physico-chemical properties of the title compounds were studied.

[Complete synthesis and properties of prostaglandins. X. Hydroxyl-containing esters of 11-deoxyprostaglandin E1]. / Polnyi sintez i svoistva prostaglandinov. X. Gidroksilsoderzhashchieéfiry 11-dezoksiprostaglandina E1.

Hydroxyl-containing 11-deoxyprostaglandin E1 esters were synthesised by using the methods of mixed anhydrides and nucleophilic displacement.

[Theoretical study of prostaglandin E2 conformation]. / Teoreticheskoe issledovanie prostranstvennoi struktury prostaglandina E2.

The theoretical conformational analysis of PGE2 has been performed using semiempirical approach and fixed values of the bond length and valence angles. A set of low-energy conformations was obtained for the alpha-chain and the whole PGE2 molecule. Unlike the PGE1 molecule, PGE2 alpha-chain prefers semifolded conformations. The hairpin structures with the parallel orientation of alpha- and omega-chains are the lowest-energy conformations of PGE2 conformations of PGE1 and PGE2. Sterically similar explain the similar biological activity of the two molecules.

[Microbiological synthesis and transformation of prostaglandins]. / Mikrobiologicheskii sintez i prevrashchenie prostaglandinov.

The review surveys current literature on microbiological synthesis and modification of prostaglandins. Three possible approaches to the use of microorganisms for prostaglandin production are considered including synthesis de novo, arachidonic acid transformation, and prostaglandin modifications. The most typical reactions of prostaglandin transformations by microorganisms are analysed: hydrolysis, hydroxylation, reduction and beta-oxidation.

[Effect of totally synthetic racemic prostaglandins F2 alpha and 15 alpha-OH-11-deoxyprostaglandin E1 on small intestine motility in rabbits with dynamic ileus]. / Vliianie total'no-sinteticheskikh ratsemicheskikh prostaglandinov F2alpha i 15alpha-OH-11-dezoksiprostaglandina E1 na motoriku tonkoi kishki krolika v usloviiakh dinamicheskoi neprokhodimosti.

A comparative analysis of the effect of racemic PGF2 alpha--(+/-)PGF2 alpha, 15 alpha OH-II-deoxy-PGE1-(+/-)DPGE1, aceclidine, neostigmine methylsufate, galanthamini hydrobromidum, and pituitrine on the ileum motility was performed in rabbits with dynamic ileus induced by surgical trauma and peritonitis. In the model under study (+/-)PGF2 alpha was similar in its action to neostigmine methylsulfate and aceclidine, with (+/-)DPGE1 having a week effect.

[Experimental study on the effect of 11-deoxyprostaglandin E1 on hormonal balance in animals]. / Eksperimental'noe issledovanie vliianiia 11-dezoksiprostaglandina El na gormonal'nyi balans zhivotnykh.

The effects of prostaglandin F2 alpha and (+/-) 11-deoxyprostaglandin E1 (DPGE) on the levels of progesterone and estradiol in the blood plasma or serum of experimental animals were studied and compared. It was found for the first time that the synthetic analog of natural PGE1, DPGE, is capable to substantially reduce the progesterone level in the blood (rats and cows) and to induce the luteolysis of yellow bodies in the cow ovaries. It was demonstrated that DPGE promotes the resolution of both cyclic and persistent yellow bodies. The pattern of the drug action on rat blood steroid hormones depends on the time of pregnancy and is most pronounced in the last trimester of pregnancy.

[Effect of 1,4-naphthoquinones on lipolysis in hemorrhagic shock]. / Vliianie nekotorykh 1,4-naftokhinonov na lipoliz pri gemorragicheskom shoke.

Derivatives of 1,4-naphthoquinones increased the lipolytic activity of epididymal and perinephric fatty tissues. A compound AK-45 Na at a dose of 30 mg/kg elevated the positive effect of rheopolyglucine on lipid metabolism, contributing to mobilization as well as to consumption of lipids in hemorrhagic shock in rats and rabbits.