Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates

Kachanov, Andrey V.; Slabko, O. Yu.; Baranova, Olga V.; Shilova, Evgenia V.; Kaminskii, V. A.

doi:10.1016/j.tetlet.2004.04.071

Cited by 70 publications

(72 citation statements)

References 14 publications

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“…Compounds 1aec were prepared by addition of selenium dioxide [23] to malononitrile in DMSO at room temperature followed by reaction with the corresponding aminoaryl derivatives. Compound 1d was obtained from 1c by reaction with acetic anhydride.…”

Section: Chemistrymentioning

confidence: 99%

“…The selection of the new compounds to be synthesized was made according to the commercial availability so as the synthetic accessibility. So, the functionalization of positions 2 and 3, in order to obtain the corresponding ortho and meta derivatives from 1a, 2a, 1b and 2b, that requires an electrophilic substitution on a deactivated position, does not occur [23]. This difficulty has not been overcome, using other synthetic methods [24e26].…”

Section: Activity In Axenic Promastigotes and Amastigotesmentioning

confidence: 99%

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Selenocyanates and diselenides: A new class of potent antileishmanial agents

Plano

Baquedano

Moreno-Mateos

et al. 2011

European Journal of Medicinal Chemistry

122

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Section: Chemistrymentioning

confidence: 99%

Section: Activity In Axenic Promastigotes and Amastigotesmentioning

confidence: 99%

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Plano

Baquedano

Moreno-Mateos

et al. 2011

European Journal of Medicinal Chemistry

122

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“…The compound 4‐H 2 NC 6 H 4 SeCN was prepared according to procedures reported in the literature 33. Other analytical grade reagents and solvents were obtained commercially (Aldrich or Sigma).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and X‐ray Structural Characterization of Di‐p‐aminobenzenediselenide [p‐H₂NC₆H₄Se]₂ and its Mercury(II) Derivatives

Bublitz

Mello

Durigon

et al. 2014

Zeitschrift anorg allge chemie

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A synthetic route to obtain [p‐H2NC6H4Se]2 (1) in good yield was developed, and the crystal structure of the product was characterized for the first time. The synthesis and structure of the mercury(II) derivative [Hg(SeC6H4NH2)2] (2) was also investigated and is reported herein. The versatile coordination chemistry of [Hg(SeC6H4NH2)2] with halides of the same metal and PCy3 allows the synthesis of [Hg(X)(SeC6H4NH2)(PCy3)] (X = Cl, Br, I) (3–5). The products 1, 3–5 were isolated in crystalline form and characterized by X‐ray structure analysis.

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“…From benzo[ c ][1,2,5]selenadizole‐5‐acyl chloride and 4‐aminophenylselenocyanate (synthesized according to the general method described in the literature) 41.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and in vitro Anticancer Activities of some Selenadiazole Derivatives

Plano

Moreno

Font

et al. 2010

Archiv der Pharmazie

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A novel series of fourteen substituted selenadiazoles has been synthesized and the compounds tested for their in vitro antiproliferative and cytotoxic activities. The tests were carried out against leukemia (CCRF-CEM), colon (HT-29), lung (HTB-54), and breast (MCF-7) cancer cells. In order to assess the selectivity of the compounds under investigation the assays were also carried out on two non-tumoral lines - one mammary (184B5) and one bronchial epithelium (BEAS-2B) cell line. Assay-based antiproliferative activity studies revealed that seven derivatives (2a, 2c, 2e, 2f, 2g, 3a, and 3b) exhibited good activity against MCF-7 cells: for instance, 2c and 2f inhibited cell growth with nanomolar GI₅₀ values. Compound 2f had a better antitumoral profile than vinorelbine and paclitaxel, two drugs that are used as first-line treatments in advanced, recurrent, and/or metastatic cancer. In the other cell lines the compounds showed moderate activity or were inactive - with the exception of 2a, which was also found to have antiproliferative activity. Modulation of the cell cycle and apoptotic effects of active compounds were further evaluated in MCF-7 cells. Of these, 6-bromo[1,2,5]selenadiazolo[3,4-b]pyridine (2a) was the most active, with an apoptogenic effect 3.9 times higher than that of camptothecin, which was used as a positive control. Compound 2a also provoked cell cycle arrest with a significant decrease in the G₀/G₁ phase cell population and an increase in S and G₂/M cells, thus suggesting mitotic arrest prior to metaphase.

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Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates

Cited by 70 publications

References 14 publications

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Synthesis and X‐ray Structural Characterization of Di‐p‐aminobenzenediselenide [p‐H₂NC₆H₄Se]₂ and its Mercury(II) Derivatives

Synthesis and in vitro Anticancer Activities of some Selenadiazole Derivatives

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Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates

Cited by 70 publications

References 14 publications

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Synthesis and X‐ray Structural Characterization of Di‐p‐aminobenzenediselenide [p‐H2NC6H4Se]2 and its Mercury(II) Derivatives

Synthesis and in vitro Anticancer Activities of some Selenadiazole Derivatives

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Synthesis and X‐ray Structural Characterization of Di‐p‐aminobenzenediselenide [p‐H₂NC₆H₄Se]₂ and its Mercury(II) Derivatives