Synthesis of 4-oxothiazolidine-2,5-diylidenes containing thioamide group based on dithiomalonamides

Обыденнов, Константин Л.; Golovko, N. A.; Kosterina, M. F.; Поспелова, T. А.; Слепухин, П. А.; Morzherin, Yu. Yu.

doi:10.1007/s11172-014-0599-2

Cited by 10 publications

(4 citation statements)

References 30 publications

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“…Dithiomalondianilide 1 is actively used as an S,S-or S,N-bidentate complexing agent [35][36][37][38][39][40][41][42][43], a lubricant [44,45] and a corrosion inhibitor [46]. However, the synthetic potential of compound 1 as a reagent for heterocyclic chemistry has not yet been fully disclosed, and heterocyclization reactions were reported in only a few papers [47][48][49][50][51][52][53][54][55][56][57][58]. As cyclic disulfides, 1,2-dithiol derivatives are of special interest in biological studies since such disulfides are particularly prone to redox reactions (for the chemistry and biological activity of disulfides, see review papers [59][60][61][62][63]).…”

Section: Synthesismentioning

confidence: 99%

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

Dotsenko,

Bespalov,

Sinotsko

et al. 2024

IJMS

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New [1,2]dithiolo[3,4-b]pyridine-5-carboxamides were synthesized through the reaction of dithiomalondianilide (N,N′-diphenyldithiomalondiamide) with 3-aryl-2-cyanoacrylamides or via a three-component reaction involving aromatic aldehydes, cyanoacetamide and dithiomalondianilide in the presence of morpholine. The structure of 6-amino-4-(2,4-dichloro- phenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamide was confirmed using X-ray crystallography. To understand the reaction mechanism in detail, density functional theory (DFT) calculations were performed with a Grimme B97-3c composite computational scheme. The results revealed that the rate-limiting step is a cyclization process leading to the closure of the 1,4-dihydropyridine ring, with an activation barrier of 28.8 kcal/mol. Some of the dithiolo[3,4-b]pyridines exhibited moderate herbicide safening effects against 2,4-D. Additionally, ADMET (Absorption, Distribution, Metabolism, Excretion, Toxicity) parameters were calculated and molecular docking studies were performed to identify potential protein targets.

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Section: Synthesismentioning

confidence: 99%

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

Dotsenko,

Bespalov,

Sinotsko

et al. 2024

IJMS

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“…Dithiomalonodiamides and, in particular, N,N'diphenyldithiomalonodiamide 1 are actively used in various chemistry fields as bidentate complexing agents [1][2][3][4][5][6], steel corrosion inhibitors [7], reagents for the Ag + extraction from chloride-containing aqueous solutions [8], and also as starting reagents for the synthesis of a number of sulfur-containing heterocyclic systems-derivatives of 1,2-dithiol [9][10][11][12][13][14], thiazole [15,16], 1,3-dithiine [17][18][19][20][21][22], [1,2]dithiolo [3,4-b]pyridine [23], 1,2,3-thiadiazole [24], thiophene [25,26], 3,5-diaminopyrazole [11,26,27], etc. (Scheme 1).…”

Section: Doi: 101134/s1070363221110037mentioning

confidence: 99%

N,N′-Diphenyldithiomalonodiamide: Structural Features, Acidic Properties, and In Silico Estimation of Biological Activity

et al. 2021

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The spectral characteristics of dithiomalondianilide ( N , N ′-diphenyldithiomalonodiamide) were studied, and the dissociation constant was determined by potentiometric titration. Quantum-chemical methods at the B3LYP-D3BJ/6-311+G (2d,p) level were used to calculate the molecular geometry and vibrational spectra of the most stable tautomeric forms of dithiomalondianilide. The bioavailability parameters were calculated, and possible protein targets were predicted by the protein ligand docking method.

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“…For materials applications of thiazolidines, see: Matsui et al (2010). For the synthesis of related compounds, see: Obydennov et al (2014 Symmetry codes: (i) Àx þ 1; y À 1 2 ; Àz; (ii) Àx þ 2; y þ 1 2 ; Àz þ 1.…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of (2Z)-2-{(5Z)-5-[3-fluoro-2-(4-phenylpiperidin-1-yl)benzylidene]-4-oxo-3-(p-tolyl)-1,3-thiazolidin-2-ylidene}-N-(p-tolyl)ethanethioamide dimethyl sulfoxide monosolvate

et al. 2015

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The title compound, C 37 H 34 FN 3 OS 2 ÁC 2 H 6 OS, was obtained by the Knoevenagel condensation. The thiazolidine ring is essentially planar (r.m.s. deviation = 0.025 Å ) and forms dihedral angles of 4.2 (3), 68.60 (14) and 39.57 (15) with the attached thioamide group, p-tolyl group benzene ring and fluoro-substituted benzene ring, respectively. The exocyclic double bonds are in a Z configuration. In the crystal, the dimethyl sulfoxide solvent molecule is connected to the main molecule via an N-HÁ Á ÁO hydrogen bond. Weak C-HÁ Á ÁO hydrogen bonds link the components of the structure into a two-dimensional network parallel to (101). Weak intramolecular C-HÁ Á ÁS hydrogen bonds are also observed. The crystal is an inversion twin with a ratio of twin components 0.78 (2):0.22 (6).

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Synthesis of 4-oxothiazolidine-2,5-diylidenes containing thioamide group based on dithiomalonamides

Cited by 10 publications

References 30 publications

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies

N,N′-Diphenyldithiomalonodiamide: Structural Features, Acidic Properties, and In Silico Estimation of Biological Activity

Crystal structure of (2Z)-2-{(5Z)-5-[3-fluoro-2-(4-phenylpiperidin-1-yl)benzylidene]-4-oxo-3-(p-tolyl)-1,3-thiazolidin-2-ylidene}-N-(p-tolyl)ethanethioamide dimethyl sulfoxide monosolvate

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