Antitumor activity of some polynitrile derivatives

Насакин, О. Е.; Lyshchikov, A. N.; Kayukov, Ya. S.; Sheverdov, V. P.

doi:10.1007/bf02524593

Cited by 29 publications

(9 citation statements)

References 4 publications

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“…Unusual processes of regiospecific quasi-hydrolysis of a cyano group and abnormal resistance of the imine moiety to be hydrolyzed in aqueous acidic media were observed in the course of the described transformation. Moreover, the intermediate 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles 3 had demonstrated a cytotoxic activity in various cancer cell lines [32], therefore the derived 3,4-dihydro-2 H -pyrans 2 are very promising for biological studies.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Ievlev

Ершов

Belikov

et al. 2016

Beilstein J. Org. Chem.

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SummaryAn efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.

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Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Ievlev

Ершов

Belikov

et al. 2016

Beilstein J. Org. Chem.

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“…The action of aqueous bromine on the equal amounts of carbonyl compounds and two equivalents of malononitrile in the presence of NaOAc in EtOH-H 2 O solution results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 43–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring [8, 16, 17] and those possessing different types of pharmacological activity [1–3, 18, 19]. The procedure utilizes inexpensive reagents; it is easily carried out and the work up is not complicated.…”

Section: Discussionmentioning

confidence: 99%

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Vereshchagin

Elinson

Stepanov

et al. 2011

ISRN Organic Chemistry

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The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.

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“…The antitumor activity was on average greater than that of carbo-and heterocycles [12] prepared from pyrrolidin-3,3,4,4-tetracarbonitriles and 4-oxoalkan-1,1,2,2-tetracarbonitriles.…”

mentioning

confidence: 83%

“…In addition, the 4-oxoalkan-1,1,2,2-tetracarbonitriles 6-imino-2,7-dioxabicyclo[3, 2, 1]octan-4,4,5-tricarbonitriles, 9-oxo-1,2,3,4b,5,6,8a,9-octahydropyrido[3 1 ,4 1 :3, 4]pyrrolo[1, 2-a]- [1,3,5]triazin-4b,8a-dicarbonitriles, 1-oxo-3a,4,5,7a-tetrahydro-1H-pyrrolo[3, 4-c]pyridin-3a,7a-dicarbonitriles, and 1,2,3,4-tetrahydropyridin-3,3,4,4-tetracarbonitriles were tested for antitumor activity [12]. The most active among them was 2-(4-bromophenyl)-5,6-tetramethylen-1,2,3,4-tetrahydropyridin-3,3,4,4-tetr acarbonitrile.…”

mentioning

confidence: 99%

Antitumor activity of polycyano-substituted carbo- and heterocycles prepared from 3-(2,2-dialkylhydrazino)-4-R-1,1,2,2-tetracyanocyclopentanes

2008

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Anticancer activity tests have been carried out at the National Cancer Institute (USA) on a series of polycyano-substituted carbo-and heterocyclic compounds synthesized from 3-(2,2-dialkylhydrazino)-4-R-1,1,2,2-tetracyanocyclopentanes. It is established that 1,1,2,2-tetracyano-substituted derivatives are the most active, showing a high activity comparable with that of reference drugs with respect to colon, ovarian, prostate, and renal cancer. The antitumor effect of the investigated compounds is explained by the presence of dialkylhydrazino-and 1,1,2,2-tetracyanoethyl moieties in their structures.Cyano-containing compounds are attracting special attention at present in the search for new antitumor agents. Thus, the cyanogenetic glucosides linamarin, lotaustralin, heterodentrin, dhurrin, amygdalin, and tetraphyllin A, which were isolated from seeds and pits of certain plants of the family Rosaceae, subfamily plum, are used in experimental oncology [1].Furthermore, several RTK-blockers [2], Ras oncogene inhibitors [3], transferase enzyme inhibitors [4], inhibitors of signal transduction from oncogenic growth factor receptors and hormones from the cell surface to the nucleus [5], blockers of biosynthesis of hormones involved in the development of breast cancer [6,7], and radio-and chemo-sensitizers for cancer therapy [8] have been found among cyano-containing compounds.Several drugs containing cyano groups are already used in medical practice to battle oncological diseases. These are the antiandrogens bicalutamide, anastrazole, and letrozole [9] and the antibiotic toyocamycin [10]. 670 0091-150X/08/4212-0670

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Antitumor activity of some polynitrile derivatives

Cited by 29 publications

References 4 publications

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Antitumor activity of polycyano-substituted carbo- and heterocycles prepared from 3-(2,2-dialkylhydrazino)-4-R-1,1,2,2-tetracyanocyclopentanes

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