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Polysulfur- and Sulfur-Nitrogen Heterocycles II

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 8023

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Prof. Dr. Oleg A. Rakitin

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N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia
Interests: heterocyclic chemistry; sulfur-nitrogen heterocycles; selenium heterocycles; synthetic methods; biologically active compounds; organic sensitizers for DSSCs and OLEDs; 1,2,3-dithiazoles; 1,2,5-thiadiazoles; 1,2,5-oxadiazoles; disulfur dichloride
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Dear Colleagues,

Heterocyclic chemistry is a vast and important subject. Many different heterocyclic systems have now been explored. In the last century, a family of structures at the border line between organic and inorganic chemistry, which are characterized by an unusually high ratio of heteroatoms (sulfur and nitrogen) to carbon, was discovered. It turned out that these structures can be of practical interest as semiconductors, liquid crystals, and agrochemical, antimicrobial, antiviral, and similar objects. This Special Issue will focus on recent advances in the synthesis, reactivity, and uses of polysulfur– and sulfur–nitrogen heterocycles.

Prof. Dr. Oleg A. Rakitin
Guest Editor

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Keywords

heterocycles
synthetic methods
medicinal, photovoltaic materials
reactivity
computational applications

Published Papers (5 papers)

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Research

17 pages, 1938 KiB

Open AccessArticle

New Aspects of the Reaction of Thioacetamide and N-Substituted Maleimides

by Yulia V. Aseeva, Nadezhda V. Stolpovskaya, Dmitriy Y. Vandyshev, Vladimir B. Sulimov, Mikhail A. Prezent, Mikhail E. Minyaev and Khidmet S. Shikhaliev

Molecules 2022, 27(24), 8800; https://doi.org/10.3390/molecules27248800 - 12 Dec 2022

Viewed by 1228

Abstract

N-Arylmaleimides are universal substrates for the synthesis of various heterocyclic compounds with a wide spectrum of biological activity. However, their reactions with thioacetamides have not been comprehensively studied. We studied the reactions of thioacetamide with N-arylmaleimides under various conditions. We established for the first time that three types of products: epithiopyrrolo[3,4-c]pyridines, pyrrolo[3,4-c]pyridines and 3,3′-thiobis(1-arylpyrrolidine-2,5-diones) can be obtained in different conditions. In all cases, two maleimide molecules are involved in the reaction. 3,3′-Thiobis(1-arylpyrrolidine-2,5-diones) are the major products when the reaction is conducted at boiling in acetic acid. When thioacetamide and N-arylmaleimide are kept in dioxane at 50 °C, epithiopyrrolo[3,4-c]pyridines can be isolated, which, when heated in dioxane, in acetic acid or in methanol in the presence of catalytic amounts of sodium methoxide, are converted into pyrrolo[3,4-c]pyridines by eliminating hydrogen sulfide. The reaction of thioacetamide and N-arylmaleimide in dioxane at boiling temperature with the portioned addition of N-arylmaleimide leads predominantly to the formation of pyrrolo[3,4-c]pyridines. The reaction of thioacetamide with N-alkylmaleimides under all the above conditions leads predominantly to the formation of the corresponding sulfides. The structure of the compounds obtained was characterized by a set of spectral analysis methods and X-ray diffraction (XRD) data. Full article

(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles II)

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12 pages, 2730 KiB

Open AccessArticle

New Cycloadditon Reaction of 2-Chloroprop-2-enethioamides with Dialkyl Acetylenedicarboxylates: Synthesis of Dialkyl 2-[4,5-bis(alkoxycarbonyl)-2-(aryl{alkyl}imino)-3(2H)-thienylidene]-1,3-dithiole-4,5-dicarboxylates

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molecules 2022, 27(20), 6887; https://doi.org/10.3390/molecules27206887 - 14 Oct 2022

Cited by 1 | Viewed by 869

Abstract

The 1,3-dipolar cycloaddition of 1,2-dithiole-3-thiones with alkynes to form 1,3-dithioles is one of the most studied reactions in this class of polysulfur-containing heterocycles. Nucleophilic substitution of chlorine atoms in dimethyl 2-(1,2-dichloro-2-thioxoethylidene)-1,3-dithiole-4,5-dicarboxylate, which was obtained by addition one molecules of DMAD to 4,5-dichloro-3H-1,2-dithiole-3-thione, led to a series of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides. Cycloaddition reaction of 2-chloro-2-(1,3-dithiol-2-ylidene)ethanethioamides with activated alkynes led to the unexpected formation of 2-(thiophen-3(2H)-ylidene)-1,3-dithioles via new intermediate, 1-(1,3-dithiol-2-ylidene)-N-phenylethan-1-yliumimidothioate. Structure of dimethyl 2-(4,5-bis(methoxycarbonyl)-2-(phenylimino)thiophen-3(2H)-ylidene)-1,3-dithiole-4,5-dicarboxylate was finally proven by single crystal X-ray diffraction study. Optimized reaction conditions and a mechanistic rationale for the 1,3-dipolar cycloaddition of novel intermediate are presented. Full article

(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles II)

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18 pages, 2942 KiB

Open AccessArticle

Synthesis of 4,5-Dihydro-1H-[1,2]dithiolo[3,4-c]quinoline-1-thione Derivatives and Their Application as Protein Kinase Inhibitors

by Svetlana M. Medvedeva and Khidmet S. Shikhaliev

Molecules 2022, 27(13), 4033; https://doi.org/10.3390/molecules27134033 - 23 Jun 2022

Cited by 4 | Viewed by 2005

Abstract

This study represents the design and synthesis of a new set of hybrid and chimeric derivatives of 4,5-dihydro-4,4-dimethyl-1H-[1,2]dithiolo[3,4-c]quinoline-1-thiones, the structure of which the tricyclic fragment linearly bound or/and condensed with another heterocyclic fragment. Using the PASS Online software, among the previously synthesized and new derivatives of 1,2-dithiolo[3,4-c]quinoline-1-thione we identified 12 substances with pleiotropic activity, including chemoprotective and antitumor activity. All the synthesized derivatives were screened for their inhibitory assessment against a number of kinases. Compounds which exhibited prominent inhibition percentage in cells (>85%) were also examined for their inhibitory efficiency on human kinases via ELISA utilizing sorafenib as a reference standard to estimate their IC₅₀ values. It was revealed that compounds 2a, 2b, 2c, and 2q displayed a significant inhibition JAK3 (IC₅₀ = 0.36 μM, 0.38 μM, 0.41 μM, and 0.46 μM, respectively); moreover, compounds 2a and 2b displayed excellent activities against NPM1-ALK (IC₅₀ = 0.54 μM, 0.25 μM, respectively), against cRAF[Y340D][Y341D], compound 2c showed excellent activity, and compound 2q showed weak activity (IC₅₀ = 0.78 μM, 5.34 μM, respectively) (sorafenib IC₅₀ = 0.78 μM, 0.43 μM, 1.95 μM, respectively). Thus, new promising preferred structures for the creation of drugs for the treatment of cancer and other multifactorial diseases in the future have been found. Full article

(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles II)

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13 pages, 5458 KiB

Open AccessArticle

Molecular Environment Effects That Modulate the Photophysical Properties of Novel 1,3-Phosphinoamines Based on 2,1,3-Benzothiadiazole

by Radmir M. Khisamov, Alexey A. Ryadun, Sergey N. Konchenko and Taisiya S. Sukhikh

Molecules 2022, 27(12), 3857; https://doi.org/10.3390/molecules27123857 - 16 Jun 2022

Cited by 3 | Viewed by 1306

Abstract

We report synthesis, crystal structure, and photophysical properties of novel 1,3-phosphinoamines based on 4-amino-2,1,3-benzothiadiazole (NH₂-btd): Ph₂PCH(Ph)NH-btd (1) and Ph₂P(E)CH(Ph)NH-btd, (E = O (2α and 2β·thf), S (3), Se (4)). Chalcogenides 2–4 exhibit bright emissions with a major band at 519–536 nm and a minor band at 840 nm. According to TD-DFT calculations, the first band is attributed to fluorescence, while the second band corresponds to phosphorescence. In the solid state, room temperature quantum yield reaches 93% in the case of the sulphide. The compounds under study feature effects of the molecular environment on the luminescent properties, which manifest themselves in fluorosolvatochromism as well as in a luminescent response to changes in crystal packing and in contributions to aggregation effects. Specifically, transformation of solid 2β·thf to solvate-free 2β either by aging or by grinding causes crystal packing changes, and, as a result, a hypsochromic shift of the emission band. Polystyrene films doped with 2 reveal a bathochromic shift upon increasing the mass fraction from 0.2 to 3.3%, which is caused by molecular aggregation effects. Full article

(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles II)

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16 pages, 3040 KiB

Open AccessArticle

Synthesis and Antimicrobial Activity Screening of Piperazines Bearing N,N′-Bis(1,3,4-thiadiazole) Moiety as Probable Enoyl-ACP Reductase Inhibitors

by Alaa Z. Omar, Najla A. Alshaye, Tawfik M. Mosa, Samir K. El-Sadany, Ezzat A. Hamed and Mohamed A. El-Atawy

Molecules 2022, 27(12), 3698; https://doi.org/10.3390/molecules27123698 - 09 Jun 2022

Cited by 10 | Viewed by 1985

Abstract

A new N,N′-disubstituted piperazine conjugated with 1,3,4-thiadiazole and 1,2,4-triazole was prepared and the chemical structures were identified by IR, NMR and elemental analysis. All the prepared compounds were tested for their antimicrobial activity. The antimicrobial results indicated that the tested compounds showed significant antibacterial activity against gram-negative strains, especially E. coli, relative to gram-positive bacteria. Docking analysis was performed to support the biological results; binding modes with the active site of enoyl reductase amino acids from E. coli showed very good scores, ranging from −6.1090 to −9.6184 kcal/mol. Correlation analysis was performed for the inhibition zone (nm) and the docking score. Full article

(This article belongs to the Special Issue Polysulfur- and Sulfur-Nitrogen Heterocycles II)

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