336190-07-9Relevant academic research and scientific papers
Antiproliferative Activity of 2-Aroyland 2-Heteroyl-1,1,3,3-Tetracyanoprop-2-en-1-ides
Kayukov, Ya. S.,Mar’yasov, M. A.,Nasakin, O. E.
, (2020/05/22)
The influence of previously synthesized 2-aroyl-1,1,3,3-tetracyanoprop-2-en-1-ides on the growth of conditionally normal and tumor cells was studied in continuation of a search for new anticancer drugs. Cytotoxicities of the compounds were studied with respect to human tumor cell lines from the ATCC. All compounds were ineffective against melanoma and lung and ovary cancer cell lines and exhibited moderate activity in the other cases. The tested compounds exhibited highly selective effects because they were safe for conditionally normal skin fibroblasts.
Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
Karpov, Sergey V.,Grigor'Ev, Arthur A.,Kayukov, Yakov S.,Karpova, Irina V.,Nasakin, Oleg E.,Tafeenko, Victor A.
, p. 6402 - 6408 (2016/08/16)
A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
New procedures for preparing 2,2,3,3-tetracyanocyclopropyl ketones
Bardasov,Kayukova,Kayukov,Ershov,Nasakin
experimental part, p. 1431 - 1434 (2010/01/05)
New procedures were developed for preparing 2,2,3,3-tetracyanocyclopropyl ketones, based on reactions of substituted glyoxals with bromomalononitrile.
Synthesis of 2,2,3,3-tetracyanocyclopropyl ketones and their reactions with oxygen-centered nucleophiles
Bardasov,Kayukova,Kayukov, Ya. S.,Ershov,Nasakin,Tafeenko
experimental part, p. 1325 - 1335 (2010/01/11)
A procedure for the synthesis of 2,2,3,3-tetracyanocyclopropyl ketones has been developed on the basis of three-component Wideqvist reaction of dihydroxymethyl ketones, 2-bromomalononitrile, and malononitrile. The presence of five electron-withdrawing groups in the resulting cyclopropyl ketones determines high acidity of proton in the cyclopropane ring. Facile deprotonation by the action of bases promotes opening of the three-membered ring with formation of either 1,1,3,3-tetracyanopropenides or (in the presence of alcohols or oximes), [2-alkoxy(aminooxy)-5-amino-4-cyanofuran-3(2H)-ylidene] malononitriles. The reaction with acetone oxime was not accompanied by cleavage of the three-membered ring, and nucleophilic attack was directed at the cyano groups in the trans position with respect to the carbonyl group to give the corresponding (1R*,5S*,6R*)-4-amino-2,2-bis(prop-2- ylideneaminooxy)-3-azabicyclo[3.1.0]hex-3-ene-1,5-dicarbonit riles.
A new route to 1-substituted 2,2,3,3-tetracyanocyclopropanes
Sheverdov,Ershov,Nasakin,Selyunina,Tikhonova,Chernushkin,Khrustalev
, p. 1251 - 1253 (2007/10/03)
2,2,3,3-Tetracyanocyclorpropyl ketones were prepared by reaction of tetracyanoethylene with α-chloro ketones.
