Arylmethylidene Derivatives Research Articles

Recognition of arylmethylidene derivatives of imidazothiazolotriazinones as novel tubulin polymerization inhibitors.

Two series of arylmethylidene derivatives of imidazothiazolotriazinone differing in the structure of the imidazothiazolotriazine fragment were synthesized and their antiproliferative activity and effect on tubulin polymerization were evaluated. Some of the synthesized derivatives showed a significant antiproliferative effect, among which (Z)-7-(2,4-dichlorobenzylidene)-1,3-diethyl-1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-2,8(3H,7H)-dione 2n exhibited the highest antiproliferative activity. The GI50 values of the compound against 56 of the 58 cell lines were 19.4-87.8 nM; against the remaining 2 cell lines, they were 0.544-1.29 μM. Moreover, further mechanism analysis demonstrated that 2n caused G2/M arrest, induced cell apoptosis in K562 cells and blocked tubulin polymerization in the same way as colchicine.

Synthesis and spectral studies of novel nicotinonitrile-based fluorescent dyes

The synthesis of novel highly efficient fluorescent dyes of 4-amino-2-chloro-6-arylpyridine-3,5-dicarbonitrile series via heterocyclization of aryl(heteryl)methylidene derivatives of malononitrile dimer bearing electron-donor groups was described. Solvatochromic behavior and substituents effect on the spectral-luminescent properties were also investigated. Strong solvatochromism and high relative fluorescence quantum yields up to 0.92 despite the large Stokes shift values and were observed.

An approach to the synthesis of α-cyanostilbazole derivatives based on the heterocyclization of tetracyanopropenides

The synthesis of α-cyanostilbazole derivatives via the heterocyclization reaction of arylmethylidene derivatives of the malononitrile trimer (YMNT-) is described. This approach opens up the possibility for the one step synthesis of α-cyanostilbazole derivatives with a highly functionalized pyridine fragment. The spectral-luminescent properties in solution as well as in the solid state were investigated. The obtained α-cyanostilbazoles, depending on the aryl ring substituents, exhibit solid-phase fluorescence from blue to red.

Micelle-Catalyzed Synthesis of Arylmethylidene Derivatives of Malononitrile Trimer and Study of Their Optical Properties

Potassium salts of arylmethylidene derivatives of malononitrile trimer were obtained by the reactions of aromatic aldehydes with malononitrile trimer in an aqueous medium under micellar catalysis. The optical properties of the synthesized salts were studied to show they absorb in the range of 313–436 nm, depending on the substituent. Exchange reactions with various metal salts showed that the synthesized derivatives of malononitrile trimer form difficultly soluble compounds with silver salts.

Cascade of Michael Addition/Retro‐Michael Reaction/Skeletal Rearrangement in the Synthesis of Arylmethylidene Derivatives of Imidazothiazolotriazines

AbstractChemo‐, regio‐ and diastereoselective approach to the synthesis of arylmethylideneimidazothiazolotriazines has been developed based on the Michael addition/retro‐Michael reaction and Michael addition/retro‐Michael reaction/skeletal rearrangement cascade processes in the reactions of imidazo[4,5‐e]thiazolo[3,2‐b][1,2,4]triazines with arylmethylidene derivatives of malononitrile.

Arylmethylidenefuranones: Reactions with C- and N-Nucleophiles

In the review, data on the reactions of arylmethylidene derivatives of 3H-furan-2-ones with C-, N-, N,N-, and N,O-nucleophilic agents and amines of the heterocyclic series are systematized. It is demonstrated that the direction of the reaction depends on the structure of initial reagents, the strength of nucleophilic agent, and the reaction conditions. A wide range of acyclic, cyclic, and heterocyclic compounds are obtained: amides, 4-oxoalkanoic hydrazides, pyrrolones, benzofurans, furopyridines, phenanthrenes, pyrosolinones, pyridazinones, oxazines, thiadiazoles, triazolediazepinones, etc.

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents.

The arylmethylidene derivatives of furan-2(3H)-ones are important building blocks for the synthesis of various heterocyclic compounds containing pyrimidine and pyridazine structural fragments, analogues of nitrogen-containing bases of pyrimidine series. In order to continue the development of constructing of molecules containing pyridine and pyridazine fragments, this article is devoted to the synthesis of new biologically active compounds with these moieties. The introduction of a heterocyclic chromenone fragment changes the previously observed 5-R-3-arylmethylidenefuran-2(3H)-ones route of reaction with guanidine carbonate and leads to 3-[(2-amino-4-(2-hydroxyphenyl)pyrimidin-5-yl)methylene]-5-phenylfuran-2(3H)-ones (2a–d). The structure of the reaction products depends on the nature of the aromatic substituent at the C-3 position of the furanone ring. The interaction of 5-aryl-3-arylmethylidenefuran-2(3H)-ones (1e–h) with thiourea in the basic medium leads to the isolation of 5-(2-oxo-2-phenylethyl)-6-aryl-2-thioxotetrahydropyrimidine-4(1H)-ones (3a–d), demonstrating pronounced plant-growth regulatory activity. Optimal conditions for all discussed processes were developed.

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Previously unknown dispiropyrrolidines were synthesized by 1,3-dipolar cycloaddition of azomethine ylide to 3-arylmethylidene-3Н-furan-2-ones. The cycloaddition reaction was demonstrated to proceed diastereoselectively through an endo-transition state. Alternative transition states for the reaction are discussed.

ChemInform Abstract: Double Heteroannulation Reactions of 1‐Naphthol with Alkyl‐ and Arylmethylidene Derivatives of Malononitrile Dimer.

AbstractThe synthesis of novel chromeno pyridine derivatives (IV) is achieved through double heteroannulation reactions of Michael adducts derived from 1‐naphthol and derivatives of malononitrile dimer.

Double heteroannulation reactions of 1-naphthol with alkyl- and arylmethylidene derivatives of malononitrile dimer

The synthesis of 7H-benzo[7,8]chromeno[2,3-b]pyridine derivatives from the reactions of arylmethylidene derivatives of malononitrile dimer with 1-naphthol is described.

Synthesis of arylmethylidene(ethylidene)furanones

The data on the methods of synthesizing arylmethylidene(ethylidene) derivatives of 3H-furan-2-ones and related compounds based on the heterocyclization of different acids and their functional derivatives as well as the condensation of heterocyclic compounds with carbonyl components, are systematized in the review.

One-pot synthesis of 2-(dicyanomethylene)-1,2-dihydropyridine derivatives

The synthesis of 2-(dicyanomethylene)-1,2-dihydropyridine derivatives from the reactions of arylmethylidene derivatives of malononitrile dimers with 1,3-dicarbonyl compounds is described.

Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers

Reaction of arylmethylidene derivatives of malononitrile dimer with 1,3-cyclohexanediones in anhydrous methanol in the presence of sodium methylate as catalyst affords 4-amino-5-aryl-2-methoxy-6-oxo-5,6,7,8,9,10-hexahydrobenzo[b][1,8]naphthyridine-3-carbonitrile. In the presence of strong electron-donor substituents in the benzene ring the reaction takes another route resulting in 4-amino-2-aryl-6-methoxypyridine-3,5-dicarbonitriles.

ChemInform Abstract: Arylmethylidene Derivatives of Furan‐2(3H)‐ones in the Synthesis of Furopyridinecarbonitriles.

ChemInform Abstract: Arylmethylidene Derivatives of Furan‐2(3H)‐ones in the Synthesis of Furopyridinecarbonitriles.

ChemInform Abstract: Heterocyclization of Arylmethylidene Derivatives of Malononitrile Dimer: Synthesis of 4‐Amino‐6‐aryl‐2‐halopyridine‐3,5‐dicarbonitriles.

AbstractHighly functionalized pyridines are prepared via nucleophilic addition of arylmethylidene derivatives of malononitrile dimer halides to hydrogen (I) followed by cyclization and aromatization under the action of SeO2 or Br2 as the oxidizing agent.

Arylmethylidene derivatives of furan-2(3H)-ones in the synthesis of furopyridinecarbonitriles

Arylmethylidene derivatives of furan-2(3H)-ones in the synthesis of furopyridinecarbonitriles

Heterocyclization of arylmethylidene derivatives of malononitrile dimer: synthesis of 4-amino-6-aryl-2-halopyridine-3,5-dicarbonitriles

The synthesis of 4-amino-6-aryl-2-halopyridine-3,5-dicarbonitriles from the reaction of arylmethylidene derivatives of malononitrile dimer with hydrohalic acid in the presence of an oxidizing agent is described.

Reaction of 5-aryl-3H-furan-2-ones and their 3-arylmethylidene derivatives with thiosemicarbazide

O The interest to 3Н-furan-2—ones and their arylmethylidene derivatives is due to the structural features. The presence of several electrophilic sites, the reciprocal position of groups makes these compounds valuable substrates for the synthesis of versatile heterocyclic systems [1]. The goal of this study was obtaining substituted triazole structures by the reactions of 5-aryl-3Нfuran-2-ones and their 3-arylmethylidene derivatives with thiosemicarbazide under the conditions of basic catalysis. Reactions of 5-aryl-3Н-furan-2-ones Ia, Ib with thiosemicarbazide were carried out in ethanol solution in the presence of a catalytic quantity of triethylamine.

ChemInform Abstract: Reaction of Bromomalononitrile with 2‐Amino‐4‐arylbuta‐1,3‐diene‐1,1,3‐tricarbonitriles.

3-Amino-4-aryl-1-dicyanomethylidene-1,3a,4,4a-tetrahydrocyclopropa[c]pyrrole-3a,4a-dicarbonitriles were synthesized by reaction of 2-amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles (arylmethylidene derivatives of malononitrile dimer) with bromomalononitrile.

Reaction of 3-Arylmethylidene-3H-furan-2-ones with 3-Amino-1,2,4-triazole as a Convenient Technique to Synthesize Condensed Diazepinones

The interaction of the arylmethylidene derivatives of 3H-furan-2-ones with 3-amino-1,2,4-triazole was studied. The structure of the final products depends on reaction conditions and reagent ratio.