1596-42-5Relevant articles and documents
It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity
Almeida, Renata G.,Barbosa, Breno P. A.,Braga, Antonio L.,Costa, Pedro M. S.,Gatto, Claudia C.,Jacob, Claus,Jardim, Guilherme A. M.,Lima, Daisy J. B.,Pereira, Cynthia L. M.,Pessoa, Claudia,Santos, Augusto C. C.,Scheide, Marcos R.,de Carvalho, Guilherme G. C.,Valen?a, Wagner O.,da Silva Júnior, Eufranio N.
supporting information, p. 1709 - 1721 (2021/11/16)
We report the synthesis of 47 new quinone-based derivativesviaclick chemistry and their subsequent evaluation against cancer cell lines and the control L929 murine fibroblast cell line. These compounds combine two redox centers, such as anortho-quinone/para-quinone or quinones/selenium with the 1,2,3-triazole nucleus. Several of these compounds present IC50values below 0.5 μM in cancer cell lines with significantly lower cytotoxicity in the control cell line L929 and good selectivity index. Hence, our study confirms the use of a complete and very diverse range of quinone compounds with potential application against certain cancer cell lines.
Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
Jana, Sripati,Koenigs, Rene M.
supporting information, p. 3653 - 3657 (2019/05/24)
The rearrangement of selenium ylides is even today almost unexplored, although it would provide access to important organoselenium compounds with broad downstream applications. In this report, the first systematic study of sigmatropic rearrangement reactions of selenium ylides using a simple rhodium catalyst with catalyst loadings as low as 0.01 mol % is described. Selenium oxide pyrolysis of the rearrangement products gives access to important 1,1-disubstituted butadienes.
Synthesis of [3-(trimethylsilyl)prop-2-yn-1-yl] selenides
Musalov,Andreev,Amosova,Larina,Potapov
, p. 1510 - 1513 (2017/12/07)
Efficient and selective methods have been developed for the synthesis of previously unknown organyl [3-(trimethylsilyl)prop-2-yn-1-yl] selenides, organyl prop-2-yn-1-yl selenides, and bis[3-(trimethylsilyl) prop-2-yn-1-yl] selenide by reactions of 3-bromo
Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights
Da Cruz, Eduardo H.G.,Silvers, Molly A.,Jardim, Guilherme A.M.,Resende, Jarbas M.,Cavalcanti, Bruno C.,Bomfim, Igor S.,Pessoa, Claudia,De Simone, Carlos A.,Botteselle, Giancarlo V.,Braga, Antonio L.,Nair, Divya K.,Namboothiri, Irishi N.N.,Boothman, David A.,Da Silva Júnior, Eufranio N.
, p. 1 - 16 (2016/07/06)
Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-11
Conjugate addition of vinylic organocuprates generated via transmetalation of phenylseleno-substituted vinylzirconates: Functionalization at the 4-position of enones
Segi, Masahito,Suzuki, Masahiro,Shintaku, Kazuki,Maeda, Hajime
experimental part, p. 545 - 552 (2012/01/05)
Hydrozirconation of propargylic selenides (1) or 4-phenylseleno-1-butyne (2) with Cp2ZrHCl, followed by in situ transmetalation to cuprate (Me2Cu(CN)Li2) and addition of enones, led to the formation of 1,4-adducts in good
Employment of palladium pincer-complexes in phenylselenylation of organohalides
Wallner, Olov A.,Szabo, Kalman J.
, p. 9215 - 9221 (2007/10/03)
Palladium pincer-complex-catalyzed selenylation of propargyl-, allyl-, benzyl-, and benzoyl halides could be achieved under mild reaction conditions employing trimethylstannylphenylselenide as selenylating agent. This reaction has a high functional group
Preparation of isoxazol(in)yl substituted selenides and their further deselenenylation reaction to synthesize 3,5-disubstituted isoxazoles
Xu, Wei Ming,Tang,Huang, Xian
, p. 501 - 506 (2007/10/03)
We report a mild 1,3-dipolar cycloaddition protocol for the preparation of 3-aryl-5-phenylselenomethyl isoxazoles and isoxazolines regioselectively. The former was further reacted with LDA and electrophilic substrates followed by selenoxide syn-eliminatio
Study toward the synthesis of selenofurans via seleno-Claisen rearrangement of allyl arylselenides
Stefani, Helio A.,Petragnani, Nicola,Ascenso, Maria F. C.,Zeni, Gilson
, p. 2161 - 2166 (2007/10/03)
Selenofuran derivatives were prepared using several phenyl alkenyl selenides via seleno-Claisen rearrangement.
A novel 3,4-bis(sulfenyl)- or 4-selenenyl-3-sulfenylpenta-2,4-dienylation of aldehydes using 4-ethoxy-1,2-bis(sulfenyl)- or 1-selenenyl-2-sulfenylbuta-1, 3-dienyl lithiums
Yoshimatsu, Mitsuhiro,Matsuura, Yasutaka,Gotoh, Kohei
, p. 1405 - 1412 (2007/10/03)
3,4-Dichalcogenopenta-2,4-dienylation of aldehydes proceeded in good to high yields using 4-ethoxy-1-(benzenesulfenyl)-2-(methanesulfenyl)- (5), 4-ethoxy-1,2-bis(benzenesulfenyl)but-1,3-diene (6), and 1-selenenyl derivatives 7 and 8. This novel four-carbo
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2007/10/03)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
