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Vol 59, No 12 (2023)
Articles
Predislovie k stat'yam, opublikovannym po materialam vserossiyskoy konferentsii s mezhdunarodnym uchastiem «Idei i nasledie A.E. Favorskogo v organicheskoy khimii» (Sankt-Peterburg, 3–6 iyulya, 2023 g.)
Žurnal organičeskoj himii. 2023;59(12):1523-1524
1523-1524
Symposium on chemistry of alkynes, allenes and small cycles
Abstract
The symposium on the chemistry of alkynes, allenes and small cycles was held from July 3 to July 6, 2023 at St. Petersburg State University as part of the All-Russian conference with international participation “Ideas and legacy of A.E. Favorsky in organic chemistry”. Leading experts in the chemistry of alkynes, allenes and small cycles took part in the symposium; the latest achievements in the chemistry of these classes of compounds were presented and further development prospects were discussed. This review contains brief annotations of the reports and references to the corresponding publications of the authors.
Žurnal organičeskoj himii. 2023;59(12):1525-1548
1525-1548
Second All-Russian school of medical chemistry for young scientists
Abstract
The second school in medicinal chemistry was held from July 3 to July 6, 2023 at St. Petersburg State University as part of the All-Russian conference with international participation “Ideas and legacy of A.E. Favorsky in organic chemistry” with the support of the St. Petersburg branch of D.I. Mendeleev Russian Chemical Society. Leading experts in the field of medicinal chemistry, young scientists and students from various institutes and universities of Russia took part in the work.
Žurnal organičeskoj himii. 2023;59(12):1549-1575
1549-1575
Seminar “New organic functional materials”
Abstract
The “New Organic Functional Materials” seminar took place at St. Petersburg University as part of the All-Russian Conference featuring international participation that centered on “Ideas and Legacy of A.E. Favorsky in Organic Chemistry” from July 3-6, 2023. The seminar featured reports on organic materials possessing luminescent, photosensitizing, magnetic, conductive properties, and biological activity. The event also discussed innovative techniques for synthesizing functional organic molecules and their crystallochemical design. The review includes concise annotations of the reports and relevant references to the speakers’ works.
Žurnal organičeskoj himii. 2023;59(12):1576-1597
1576-1597
Synthesis and antituberculosis activity of new 5-alkynyl derivatives of 2-thiouridine: application of new scaffold
Abstract
We herein describe new potent inhibitors of mycobacteria based on 5-substituted 2-thiouridine derivatives. A series of new 5-alkynyl-substituted 2-thiouridine derivatives were synthesized via palladium-catalysed Sonogashira cross-coupling reaction of 5-iodo-2-thiopyrimidine base with terminal acetylenes with good yields in DMF at room temperature. It was found that sulfur atom in C2 position of pyrimidine ring had no impact on yields of target compounds. All obtained compounds were evaluated for their antimycobacterial activity against Mycobacetrium bovis and Mycobacterium tuberculosis at concentrations of 0.1-100 µg/ml using MABA test. Synthesized nucleosides showed high antimycobacterial activity against Mycobacterium bovis and Mycobacteri um tuberculosis. The obtained MIC50 values of 2-thionucleosides 14, 15 and 16 (0.28-0.75 µg/ml) significantly exceed characteristics of reference drug rifampicin, D-cycloserine and isoniazid, which gives prerequisites for further more detailed studies.
Žurnal organičeskoj himii. 2023;59(12):1598-1607
1598-1607
Design, synthesis and antiarrhythmic activity of new amide derivatives of indole-3-carboxylic acid
Abstract
The hERG (human ether-à-go-go-related gene) potassium channel has elicited intense scientific interest due to its counter-intuitive kinetics and its association with arrhythmia and sudden death. Kv1.5 potassium channel, encoded by KCNA5, is a promising target for the treatment of atrial fibrillation, one of the common arrhythmia. A new indole derivatives were synthesized via reaction of indole-3-carboxylic acid with 4-[2-(diethylamino)ethoxy]aniline under peptide coupling protocol in DMF with good yields and evaluated their antiarrythmic activity. Among them, 2-butyl- N -{4-[2-(diethylamino)ethoxy]phenyl}-1-(2-fluorobenzoyl)-1 H -indole-3-carboxamide 34 showed preferable anti-arrhythmic effects and favoured safety. These results indicate that lead compound can be a promising antiarrythmic drug for further studies.
Žurnal organičeskoj himii. 2023;59(12):1608-1619
1608-1619
Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones
Abstract
Synthesis of β-iodovinyl sulfones was performed out by direct bifunctionalization of internal alkynes using an economical LED light source with a maximum emission wavelength of 625 nm. The products were obtained in high yields (68 to 99%) using equivalent amounts of reagents. The reaction of arylsulfonyl iodides with internal alkynes proceeds by a radical mechanism and is a regioselective method for the synthesis of β-iodovinyl sulfones.
Žurnal organičeskoj himii. 2023;59(12):1620-1625
1620-1625
Studies of N-arylation of adamantane-containing amines using Chan-Lam reaction
Abstract
Optimization of the conditions of the Chan-Lam reaction was carried out to obtain N -aryl derivatives of adamantane-containing amines. Under optimal conditions [2 equiv p -tolylboronic acid, 2 equiv. DBU, 0.1 M solution in MeCN, 20 mol % Cu(OAc)2·H2O, 25°C, 24 h] reactions with a series of adamantane-containing amines and diamines, differing by the steric hindrances at the amino group, were performed. Strong dependence of the amine reactivity on their structure was observed, the best yield of the monoamine derivatives reached 74% and that of diamines - 66%.
Žurnal organičeskoj himii. 2023;59(12):1626-1636
1626-1636
1637-1643
Synchronous and zwitter-ion channels of (R)-5-methyl2-(1-methylethylidene)-cyclohexanone reaction with 4-phenyl-4H-1,2,4-triazoline-3,5-dione
Abstract
The interaction of pulegone with enophil - 4-phenyl-4 H -1,2,4-triazoline-3,5-dione leads to the formation of two described earlier epimers: 1-[(1 R ,4 R )-4-methyl-1-(1-methylethenyl)-2-oxocyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-dione ( RR -isomer) and 1-[(1 S ,4 R )-4-methyl-1-(1-methylethenyl)-2-oxocyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-dione ( SR -isomer). Along with these epimers, we found another isomer - 1-{1-methyl-1-[(4 R )-4methyl-6-oxocyclohex-1-en-1-yl]ethyl}-4-phenyl-1,2,4-triazolidine-3,5-dione. Quantum chemical modeling has established that isomeric products of hydrogen substitution in pulegone by enophil are formed along three routes. In the SR -isomer formation route, the ene reaction proceeds consistently. The other two routes are implemented with the enophil approach from the R -side of the pulegon. These routes consist of two consecutive stages. At the first stage, an intermediate of the type of asymmetric cyclic aziridine cation is formed. Elimination of a proton from one of the geminal methyl groups of the intermediate leads to an RR -isomer with a terminal double bond. When a proton is eliminated from the methylene group of the pulegog ring, an internal unsaturated compound is formed. The ratio of the yield of the isomer with an internal double binding and the RR -isomer depends on the polarity of the aprotic solvents.
Žurnal organičeskoj himii. 2023;59(12):1644-1652
1644-1652
Heterocyclization of fullerene with trifluoromethanesulfonamide
Abstract
The reaction of fullerene with trifluoromethanesulfonamide (triflamide), N , N -dichlorotriflamide and N -trifluoromethylsulfonyl(phenyl)iodinane in the presence of N -iodosuccinimide was studied. A single product of the aza[60]fulleroid structure was isolated.
Žurnal organičeskoj himii. 2023;59(12):1653-1656
1653-1656