Cargando…

Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity

[Image: see text] The metal-free cascade transformation of geldanamycin benzoquinone core is proposed at relatively mild conditions. This approach yields new benzoxazole ansamycin antibiotics and enables their functionalization in an atom-economic manner, irrespective of the type of amine used. The...

Descripción completa

Detalles Bibliográficos
Autores principales:	Skrzypczak, Natalia, Pyta, Krystian, Bohusz, Wiktor, Leśniewska, Aleksandra, Gdaniec, Maria, Ruszkowski, Piotr, Schilf, Wojciech, Bartl, Franz, Przybylski, Piotr
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2023
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10337034/ https://www.ncbi.nlm.nih.gov/pubmed/37276434 http://dx.doi.org/10.1021/acs.joc.3c00493

Ejemplares similares

Regioselective approach to colchiceine tropolone ring functionalization at C(9) and C(10) yielding new anticancer hybrid derivatives containing heterocyclic structural motifs
por: Pyta, Krystian, et al.
Publicado: (2022)

Anticancer activity and toxicity of new quaternary ammonium geldanamycin derivative salts and their mixtures with potentiators
por: Skrzypczak, Natalia, et al.
Publicado: (2021)

An Approach to Modify 14-Membered Lactone Macrolide Antibiotic Scaffolds
por: Janas, Anna, et al.
Publicado: (2022)

New Ansamycins from the Deep-Sea-Derived Bacterium Ochrobactrum sp. OUCMDZ-2164
por: Fan, Yaqin, et al.
Publicado: (2018)

Cholinesterases Inhibition, Anticancer and Antioxidant Activity of Novel Benzoxazole and Naphthoxazole Analogs
por: Skrzypek, Alicja, et al.
Publicado: (2022)

Mode of Action of Kanglemycin A, an Ansamycin Natural Product that Is Active against Rifampicin-Resistant Mycobacterium tuberculosis
por: Mosaei, Hamed, et al.
Publicado: (2018)

o-Benzoquinone dioxime
por: Gervasio, Giuliana, et al.
Publicado: (2010)

Design, synthesis and biological potential of heterocyclic benzoxazole scaffolds as promising antimicrobial and anticancer agents
por: Kakkar, Saloni, et al.
Publicado: (2018)

Analgesic and Anticancer Activity of Benzoxazole Clubbed 2-Pyrrolidinones as Novel Inhibitors of Monoacylglycerol Lipase
por: Afzal, Obaid, et al.
Publicado: (2021)

Molecular-docking-guided design, palladium-catalyzed synthesis and anticancer activity of paclitaxel-benzoxazoles hybrids
por: Jiang, Ting, et al.
Publicado: (2022)

Novel polymeric derivatives of betulin with anticancer activity
por: Niewolik, Daria, et al.
Publicado: (2019)

Dual C–H activation: Rh(iii)-catalyzed cascade π-extended annulation of 2-arylindole with benzoquinone
por: Zhang, Qijing, et al.
Publicado: (2021)

Synthesis, Structure and Cytotoxic Properties of Copper(II) Complexes of 2-Iminocoumarins Bearing a 1,3,5-Triazine or Benzoxazole/Benzothiazole Moiety
por: Makowska, Anna, et al.
Publicado: (2022)

Synergistic catalysis: cis-cyclopropanation of benzoxazoles
por: Meazza, Marta, et al.
Publicado: (2016)

The Ansamycin Antibiotic, Rifamycin SV, Inhibits BCL6 Transcriptional Repression and Forms a Complex with the BCL6-BTB/POZ Domain
por: Evans, Sian E., et al.
Publicado: (2014)

Streptomyces rugosispiralis sp. nov., a Novel Actinobacterium Isolated from Peat Swamp Forest Soil That Produces Ansamycin Derivatives and Nocardamines
por: Weeraphan, Trinset, et al.
Publicado: (2023)

Benzoxazole derivatives: design, synthesis and biological evaluation
por: Kakkar, Saloni, et al.
Publicado: (2018)

Highly Lipophilic Benzoxazoles with Potential Antibacterial Activity
por: Vinšová, Jarmila, et al.
Publicado: (2005)

Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway
por: Rocha, Daniele F. O., et al.
Publicado: (2013)

Effects of Benzoquinones on Radicles of Orobanche and Phelipanche Species
por: Fernández-Aparicio, Mónica, et al.
Publicado: (2021)

Thymoquinone (2-Isoprpyl-5-methyl-1, 4-benzoquinone) as a chemopreventive/anticancer agent: Chemistry and biological effects
por: Ahmad, Anas, et al.
Publicado: (2019)

Design, synthesis and evaluation of anticancer activity of novel 2-thioxoimidazolidin-4-one derivatives bearing pyrazole, triazole and benzoxazole moieties
por: Elhady, Heba A., et al.
Publicado: (2018)

5-Iodo-3-phenyl-2,1-benzoxazole
por: Teslenko, Yuriy, et al.
Publicado: (2013)

Palladium-Catalyzed Direct C=H Functionalization of Benzoquinone**
por: Walker, Sarah E, et al.
Publicado: (2014)

A mechanism for 1,4-Benzoquinone-induced genotoxicity
por: Son, Mi Young, et al.
Publicado: (2016)

Benzoquinone Enhances Hyperpolarization of Surface Alcohols with Para-Hydrogen
por: Norcott, Philip L.
Publicado: (2023)

In silico studies of a novel scaffold of benzoxazole derivatives as anticancer agents by 3D-QSAR, molecular docking and molecular dynamics simulations
por: Jiang, Yuhan, et al.
Publicado: (2023)

5-tert-Butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)-2-thienyl]-1,3-benzoxazole
por: Li, Yu-Feng, et al.
Publicado: (2008)

Seasonal interest in pectus excavatum and pectus carinatum: a retrospective analysis of Google Trends data
por: Skrzypczak, Piotr, et al.
Publicado: (2021)

2-(1,3-Benzoxazol-2-yl)guanidinium chloride
por: Mohamed, Shaaban K., et al.
Publicado: (2011)

2-(4-Aminophenyl)-1,3-benzoxazole
por: Qu, Yuan, et al.
Publicado: (2008)

Crystal Structure and Stereochemistry Study of 2-Substituted Benzoxazole Derivatives
por: Mabied, Ahmed F., et al.
Publicado: (2014)

Exploring the biocombinatorial potential of benzoxazoles: generation of novel caboxamycin derivatives
por: Losada, Armando A., et al.
Publicado: (2017)

Benzoxazole-Based Metal Complexes to Reverse Multidrug Resistance in Bacteria
por: Kincses, Annamária, et al.
Publicado: (2020)

In Vitro Anti-Candida Activity and Action Mode of Benzoxazole Derivatives
por: Staniszewska, Monika, et al.
Publicado: (2021)

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes
por: Tran, Phuong Hoang, et al.
Publicado: (2018)

Design, Synthesis, and Anti-Fungal Evaluation of Heterocyclic Benzoxazole Derivatives
por: Wang, Ruibo, et al.
Publicado: (2022)

Research Progress of Benzothiazole and Benzoxazole Derivatives in the Discovery of Agricultural Chemicals
por: Zou, Yue, et al.
Publicado: (2023)

Inhibition of constitutive and cxc-chemokine-induced NF-κB activity potentiates ansamycin-based HSP90-inhibitor cytotoxicity in castrate-resistant prostate cancer cells
por: Seaton, A, et al.
Publicado: (2009)

Identification of benzoquinones in pretreated lignocellulosic feedstocks and inhibitory effects on yeast
por: Stagge, Stefan, et al.
Publicado: (2015)

Cannot write session to /tmp/vufind_sessions/sess_pe8akmbri6r66rofpem4ntkqia