通过乙烯基吲哚的酸催化氢芳基化反应合成双吲哚甲烷及其初步生物学研究
Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.
作者信息
Pathak Tejas P, Osiak Jaroslaw G, Vaden Rachel M, Welm Bryan E, Sigman Matthew S
机构信息
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112.
出版信息
Tetrahedron. 2012 Jul 1;68(26):5203-5208. doi: 10.1016/j.tet.2012.03.075.
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.
摘要
报道了一种乙烯基吲哚的酸催化氢芳基化反应，该反应能够耐受多种杂环作为外源亲核试剂，如吲哚、吡咯和中氮茚。该方法能以良好至优异的产率快速得到具有生物学相关性的双吲哚甲烷骨架。对几种合成类似物的生物活性评估显示，它们对MCF-7乳腺癌细胞系具有细胞毒性活性和选择性。
相似文献
1
Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.
Tetrahedron. 2012 Jul 1;68(26):5203-5208. doi: 10.1016/j.tet.2012.03.075.
2
Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.
Org Lett. 2011 May 20;13(10):2774-7. doi: 10.1021/ol200913r. Epub 2011 Apr 21.
3
Gold-Catalyzed cis-Hydroarylation of Ynamides with Indoles: Regio- and Stereoselective Synthesis of a Class of 2-Vinylindoles.
Org Lett. 2016 Oct 7;18(19):4798-4801. doi: 10.1021/acs.orglett.6b02189. Epub 2016 Sep 9.
4
Brønsted Acid Catalyzed [3+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2-a]indoles.
Chemistry. 2016 May 17;22(21):7074-8. doi: 10.1002/chem.201601020. Epub 2016 Mar 30.
5
Formal [4+2] reaction between 1,3-diynes and pyrroles: gold(I)-catalyzed indole synthesis by double hydroarylation.
Chemistry. 2015 Jan 19;21(4):1463-7. doi: 10.1002/chem.201405903. Epub 2014 Nov 28.
6
Application of 3-Alkyl-2-vinylindoles in Catalytic Asymmetric Dearomative (2+3) Cycloadditions.
J Org Chem. 2021 Aug 6;86(15):10427-10439. doi: 10.1021/acs.joc.1c01105. Epub 2021 Jul 27.
7
Palladium-catalyzed oxidative cross-coupling of N-tosylhydrazones with indoles: synthesis of N-vinylindoles.
Org Lett. 2013 Jun 21;15(12):3022-5. doi: 10.1021/ol401217h. Epub 2013 Jun 4.
8
Metal-free, Phosphoric Acid-catalyzed Regioselective 1,6-Hydroarylation of para-Quinone Methides with Indoles in Water.
Chem Asian J. 2022 May 2;17(9):e202200042. doi: 10.1002/asia.202200042. Epub 2022 Mar 24.
9
Silver-catalyzed cyclization of 2-pyridyl alkynyl carbinols with isocyanides: divergent synthesis of indolizines and pyrroles.
Chem Commun (Camb). 2014 Oct 14;50(80):11837-9. doi: 10.1039/c4cc04905e.
10
Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2 H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1 H-pyrrolizines.
Org Lett. 2019 Jan 18;21(2):519-523. doi: 10.1021/acs.orglett.8b03833. Epub 2019 Jan 8.
引用本文的文献
1
Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative.
J Org Chem. 2024 Jun 21;89(12):8620-8631. doi: 10.1021/acs.joc.4c00552. Epub 2024 May 29.
2
Efficient Green Synthesis, Anticancer Activity, and Molecular Docking Studies of Indolemethanes Using a Bioglycerol-Based Carbon Sulfonic Acid Catalyst.
ACS Omega. 2023 Sep 20;8(39):36401-36411. doi: 10.1021/acsomega.3c05293. eCollection 2023 Oct 3.
3
Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety.
RSC Adv. 2023 Jun 22;13(27):18964-18973. doi: 10.1039/d3ra03480a. eCollection 2023 Jun 15.
4
Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center.
Beilstein J Org Chem. 2021 Jun 18;17:1464-1475. doi: 10.3762/bjoc.17.102. eCollection 2021.
5
Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers.
Angew Chem Int Ed Engl. 2019 Oct 21;58(43):15386-15389. doi: 10.1002/anie.201909852. Epub 2019 Sep 12.
6
Stereospecific nickel-catalyzed cross-coupling reactions of alkyl Grignard reagents and identification of selective anti-breast-cancer agents.
Angew Chem Int Ed Engl. 2014 Feb 24;53(9):2422-2427. doi: 10.1002/anie.201308666. Epub 2014 Jan 29.
本文引用的文献
1
Chiral Brønsted acid catalyzed pinacol rearrangement.
Angew Chem Int Ed Engl. 2010 Dec 10;49(50):9734-6. doi: 10.1002/anie.201004778.
2
Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.
J Am Chem Soc. 2010 Jun 16;132(23):7870-1. doi: 10.1021/ja103472a.
3
Synthesis of biindole-diazo conjugates as a colorimetric anion receptor.
Org Lett. 2010 Jun 4;12(11):2634-7. doi: 10.1021/ol100830b.
4
Synthesis of 3-substituted indoles via reactive alkylideneindolenine intermediates.
Org Biomol Chem. 2010 Mar 21;8(6):1259-70. doi: 10.1039/b919891a. Epub 2009 Dec 16.
5
Bis- and trisindolylmethanes (BIMs and TIMs).
Chem Rev. 2010 Apr 14;110(4):2250-93. doi: 10.1021/cr900195a.
6
One-pot synthesis of symmetric and unsymmetric 1,1-bis-indolylmethanes via tandem iron-catalyzed C-H bond oxidation and C-O bond cleavage.
J Org Chem. 2009 Nov 20;74(22):8848-51. doi: 10.1021/jo902093p.
7
Highly enantioselective alkylation reaction of enamides by Brønsted-acid catalysis.
Org Lett. 2009 Oct 15;11(20):4620-3. doi: 10.1021/ol901892s.
8
Exploring bis-(indolyl)methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors.
Bioorg Med Chem Lett. 2009 May 15;19(10):2840-3. doi: 10.1016/j.bmcl.2009.03.101. Epub 2009 Mar 26.
9
Novel 2-step synthetic indole compound 1,1,3-tri(3-indolyl)cyclohexane inhibits cancer cell growth in lung cancer cells and xenograft models.
Cancer. 2008 Aug 15;113(4):815-25. doi: 10.1002/cncr.23619.
10
Cancer chemotherapy with indole-3-carbinol, bis(3'-indolyl)methane and synthetic analogs.
Cancer Lett. 2008 Oct 8;269(2):326-38. doi: 10.1016/j.canlet.2008.04.021. Epub 2008 May 22.
Zotero 插件