Literature DB >> 22778488

Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Tejas P Pathak1, Jaroslaw G Osiak, Rachel M Vaden, Bryan E Welm, Matthew S Sigman.   

Abstract

An acid-catalyzed hydroarylation reaction of vinyl indoles is reported, which tolerates a wide range of heterocycles as the exogenous nucleophile such as indoles, pyrroles, and indolizines. The method rapidly accesses the biologically relevant bisindolylmethane scaffold in good to excellent yields. Evaluation of the biological activity of several synthesized analogues reveals cytotoxic activity against and selectivity for the MCF-7 breast cancer cell line.

Entities:  

Year:  2012        PMID： 22778488      PMCID： PMC3390940          DOI： 10.1016/j.tet.2012.03.075

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  24 in total

1.  Ligand-independent activation of estrogen receptor function by 3, 3'-diindolylmethane in human breast cancer cells.

Authors:  J E Riby; G H Chang; G L Firestone; L F Bjeldanes
Journal:  Biochem Pharmacol       Date:  2000-07-15       Impact factor: 5.858

2.  Chiral Brønsted acid catalyzed pinacol rearrangement.

Authors:  Tao Liang; Zhenjie Zhang; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-10       Impact factor: 15.336

3.  Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Authors:  Tejas P Pathak; Keith M Gligorich; Bryan E Welm; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

4.  Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Authors:  Zigang Li; Junliang Zhang; Chad Brouwer; Cai-Guang Yang; Nicholas W Reich; Chuan He
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

5.  Bcl-2 family-mediated apoptotic effects of 3,3'-diindolylmethane (DIM) in human breast cancer cells.

Authors:  Chibo Hong; Gary L Firestone; Leonard F Bjeldanes
Journal:  Biochem Pharmacol       Date:  2002-03-15       Impact factor: 5.858

6.  Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents.

Authors:  Mary M Rozenman; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-11-10       Impact factor: 15.419

7.  3,3'-diindolylmethane and paclitaxel act synergistically to promote apoptosis in HER2/Neu human breast cancer cells.

Authors:  K P McGuire; N Ngoubilly; M Neavyn; S Lanza-Jacoby
Journal:  J Surg Res       Date:  2006-03-31       Impact factor: 2.192

8.  Pyrazole-based cathepsin S inhibitors with improved cellular potency.

Authors:  Jianmei Wei; Barbara A Pio; Hui Cai; Steven P Meduna; Siquan Sun; Yin Gu; Wen Jiang; Robin L Thurmond; Lars Karlsson; James P Edwards
Journal:  Bioorg Med Chem Lett       Date:  2007-08-22       Impact factor: 2.823

9.  One-pot synthesis of symmetric and unsymmetric 1,1-bis-indolylmethanes via tandem iron-catalyzed C-H bond oxidation and C-O bond cleavage.

Authors:  Xingwei Guo; Shiguang Pan; Jinhua Liu; Zhiping Li
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

10.  Highly enantioselective alkylation reaction of enamides by Brønsted-acid catalysis.

Authors:  Qi-Xiang Guo; Yun-Gui Peng; Jin-Wei Zhang; Liu Song; Zhang Feng; Liu-Zhu Gong
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005
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  3 in total

1.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.

Authors:  Ivelina M Yonova; A George Johnson; Charlotte A Osborne; Curtis E Moore; Naomi S Morrissette; Elizabeth R Jarvo
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

2.  Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.

Authors:  Johannes C L Walker; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

3.  Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center.

Authors:  Thanigaimalai Pillaiyar; Masoud Sedaghati; Andhika B Mahardhika; Lukas L Wendt; Christa E Müller
Journal:  Beilstein J Org Chem       Date:  2021-06-18       Impact factor: 2.883
  3 in total

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