Russian Journal of Organic Chemistry最新文献

An effective synthesis of optically pure macrocyclic polylactones is developed, involving the [1+1] condensation of a natural triol (castor oil) with thionyl chloride in carbon tetrachloride in the presence of DMF as a base and (N,N-dimethylamino)pyridine as a catalyst and followed by the [1+1] condensation of the resulting macrocyclic alcohol with sebacoyl chloride under similar conditions.

A series of Betti base derivatives were synthesized by the one-pot three-component DBU-catalyzed condensation of 6-bromonaphthalen-2-ol, qinolin-3-amine, and substituted benzaldehydes under mild reaction conditions and characterized by IR and NMR spectroscopy and mass spectrometry. In vitro α-amylase inhibition assay showed that the synthesized compounds compare in potency with the antidiabetic drug Acarbose, while one of the derivatives (R = 4-CF₃) showed a superior activity than Ascarbose. In silico docking studies correlated the inhibitory potency with strong binding affinity, particularly for compounds bearing electron-acceptor substituents (F, NO₂, and CF₃). The results of the α-amylase assay and molecular docking suggest that the synthesized Betti base derivatives are promising candidates for further development as α-amylase inhibitors, with potential applications in antidiabetic therapies.

Density functional theory calculations were used to investigate the structural and electronic properties of three halogen-substituted indeno[1,2-b]quinoxaline–oxazole derivatives: (E)-5-(4-bromophenyl)-2-[2-(7,8-dimethyl-11H-indeno[1,2-b]quinoxalin-11-ylidene)hydrazinyl]oxazole, (E)-5-(4-chlorophenyl)-2-[2-(7,8-dimethyl-11H-indeno[1,2-b]quinoxalin-11-ylidene)hydrazinyl]oxazole, and (E)-2-[2-(7,8-dimethyl-11H-indeno[1,2-b]quinoxalin-11-ylidene)hydrazinyl]-5-(4-fluorophenyl)oxazole. Stable molecular structures for all the three compounds were confirmed through geometry optimization at the RB3LYP/3-21G level of theory. Electronic structure analysis revealed that the frontier molecular orbital energy gaps are strongly influenced by the halogen substituent: ΔE_gap 3.44 eV (Br), 1.79 eV (Cl), and 1.75 eV (F). These variations indicate differences in molecular reactivity, charge transfer properties, and optoelectronic potential. Electrostatic potential (ESP) mapping further elucidated charge distribution patterns, highlighting electrophilic and nucleophilic regions. The findings provide valuable insights into the electronic modulation of the studied quinoxaline–oxazole derivatives, making them promising candidates for optoelectronic and material science applications.

New conjugates were synthesized by the reaction of acetylsalicylic acid chlorides, naproxen, ibuprofen, and ketoprofen with 2- and 6-aminomaleopimaric acid derivatives. The structures of the synthesized compounds were proven by IR and ¹H and ¹³C NMR spectroscopy, mass spectrometry, and elemental analysis.

A method for the synthesis of 1,1,1-(6-methyl-1-aryl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanones by the reaction of 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione with anilines in the presence of catalytic amounts of acetic acid was developed. It was found that the reactivity of substituted anilines in the studied reaction depends on the nature and position of the substituent, decreasing in the series: 2,4-Me₂-С₆H₃NH₂ > С₆H₅NH₂ 4-Me-С₆H₄NH₂ 2-Me-С₆H₄NH₂ > 3-Me-С₆H₄NH₂ 2-MeO-С₆H₄NH₂ > 4-MeC(O)-С₆H₄NH₂ 4-Br-С₆H₄NH₂.

Ethyl esters of 4-spiro-fused 6,7-dimethoxydihydroisoquinoline-1-carboxylatic acids were reduced to the corresponding 1-(hydroxymethyl)tetrahydroisoquinolines. The latter were cyclized with Formalin to form oxazoloisoquinolines, which were then recyclized into tetrahydropyranoisoquinolines by treatment with hydrobromic and concentrated hydrochloric acids. Spiro-fused 1-(hydroxymethyl)isoquinoline-6,7-diols were reacted with dibromoethane to obtain the corresponding dioxinoisoquinolines.

A series of novel chalcone derivatives bearing a pyridylisoxazole–benzoxazole moiety were synthesized and evaluated for in vitro anticancer activity against four human cancer cell lines. The majority of the synthesized compounds exhibited significant anticancer potency. Among them, six compounds demonstrated activity comparable to the reference drug etoposide, and one derivative, 1-(3,5-dinitrophenyl)-3-{2-[4-(pyridin-4-yl)isoxazol-3-yl]benzo[d]oxazol-5-yl}prop-2-en-1-one, was found to be more potent than the positive control.

Dimethyl acetals of N-tosyl-2-(5-oxopentanoyl)-, N-tosyl-2-(6-oxohexanoyl)-, and N-pivaloyl-2-(5-oxohexanoyl)anilines have been synthesized. The resulting acetals, as well as 5-(2-[(benzoylamino)-3-methylphenyl]-5-oxopentanoic acid and its methyl ester were reacted with hydroxylamine to obtain the corresponding ketoximes as syn/anti isomer mixtures.

4-Aryl-2,4-dioxobutanoic acids react with 3-nitro- and 4-nitrobenzohydrazides in a 1 : 2 ratio to form the corresponding 3-aryl-1-(3-nitrobenzoyl)-5-[2-(3-nitrobenzoyl)hydrazinyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acids and 3-aryl-1-(4-nitrobenzoyl)-5-[2-(4-nitrobenzoyl)hydrazinyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acids. The structure of the products was confirmed by X-ray diffraction analysis. The reaction proceeds under mild, catalyst-free conditions to give high yields, and the products were isolated without column chromatography. The synthesized compounds exhibit potential for diverse biological activities.

Two new series of compounds containing azomethine (–CH=N–) and sulfonamide (–SO₂NH–) linkages―(E)-4-[(4-alkoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamides and (E)-4-[(4-alkoxy-3-methoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamides, each of 7 derivatives―were synthesized, and their mesogenic behavior was investigated. Optical polarizing microscopy with a heating stage was used to determine phase transition temperatures, revealing that ten synthesized compounds exhibited nematic mesophases. The transition temperatures decreased with increasing alkyl chain length, while the lateral ortho-methoxyl substitution in the phenyl ring in (E)-4-[(4-alkoxy-3-methoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamides further reduced mesophase stability due to steric hindrance and disrupted molecular packing. The products exhibited enantiotropic nematic mesomorphism, with transition temperatures following an expected trend. Density functional theory calculations provided insights into the molecular geometries, electronic properties, and intermolecular interactions of the synthesized compounds. The HOMO–LUMO energy gaps indicated a higher stability of (E)-4-[(4-alkoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamides compared to (E)-4-[(4-alkoxy-3-methoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamides. Molecular electrostatic potential maps highlighted charge distributions influencing self-assembly and mesophase formation.