The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N, N-dimethylformamide and subsequent trapping with sulfur ylide. Moreover, this transformation has a broad range of substrate scope with a high functional-group tolerance. This new reaction was successfully utilized in the synthesis of the potent CYP19 aromatase inhibitor and late-stage functionalization on the bioactive complex estrone.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b00360 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis and Biological Evaluation of Novel 2-Aroyl Benzofuran-Based Hydroxamic Acids as Antimicrotubule Agents.
Int J Mol Sci
July 2024
Department of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, 44121 Ferrara, Italy.
Because of synergism between tubulin and HDAC inhibitors, we used the pharmacophore fusion strategy to generate potential tubulin-HDAC dual inhibitors. Drug design was based on the introduction of a -hydroxyacrylamide or a -hydroxypropiolamide at the 5-position of the 2-aroylbenzo[]furan skeleton, to produce compounds - and -, respectively. Among the synthesized compounds, derivatives , , , , and showed excellent antiproliferative activity, with IC values at single- or double-digit nanomolar levels, against the A549, HT-29, and MCF-7 cells resistant towards the control compound combretastatin A-4 (CA-4).
View Article and Find Full Text PDFSynthesis and Anticancer Activity of Rhopaladins' Analog RPDPD Against the HeLa Human Cervical Cancer Cell Line.
Front Chem
June 2022
Sinopharm Dongfeng General Hospital, Hubei University of Medicine, Shiyan, China.
Heterocyclic compounds were widely used in many domains; pyrrolidone is a derivative of heterocycles that can be used to synthesize anticancer drugs. A new fluorine-containing rhopaladins' analog()-2-(4-bromobenzoyl)--(tert-butyl)-4-(4-fluoro benzylidene)-5-oxo-1-propylpyrrolidine-2-carboxamide (RPDPD for short) of 2-aroyl-4-arylidene-5-oxopyrrolidine derivative was synthesized by the one-pot synthesis method and evaluated for its anti-tumor activity CCK8 assay and annexin V/propidium iodide (PI) staining of HeLa cells. The results exhibited that compound RPDPD has inhibited the proliferation of HeLa in a dose-dependent manner with an IC of 24.
View Article and Find Full Text PDFSynthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism.
Turk J Chem
October 2021
Muradiye Vocational School, Van Yüzüncü Yıl University, Van Turkey.
In this study, nine different C-2 aroyl imidazole derivatives were synthesized in a one pot reaction with two steps, and the reduction reactions of these derivatives with NaBH were carried out under mild conditions. Substitution reaction of obtained imidazo methanol derivatives with chloroacetylchloride reagent and ring reaction of substitution products were investigated. It was determined that 1,4-imidazoxazinone derivative was obtained as a result of the cyclization reaction.
View Article and Find Full Text PDFVisible-light driven regioselective synthesis, characterization and binding studies of 2-aroyl-3-methyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidines with DNA and BSA using biophysical and computational techniques.
Sci Rep
November 2021
Department of Chemistry, University of Delhi, New Delhi, 110007, India.
In recent times, fused azaheterocycles emerged as impressive therapeutic agents. Binding studies of such azaheterocycles with biomolecules is an important subject for pharmaceutical and biochemical studies aiming at the design and development of new drugs. Fused heterocyclic scaffolds, such as thiazolopyrmidines have long been used in the pharmaceutical industry for the treatment of various diseases.
View Article and Find Full Text PDFDiastereoselective desymmetrization reactions of prochiral para-quinamines with cyclopropenes generated in situ: access to fused hydroindol-5-one scaffolds.
Org Biomol Chem
September 2021
Department of Chemistry, Indian Institute of Technology Indore, Simrol, 453552, India.
Interesting desymmetric [3 + 2] annulation reactions between p-quinamines as prochiral N-donors and 2-aroyl-1-chlorocyclopropanecarboxylates facilitated by a base are reported. This successive double Michael reaction delivered a unique class of cyclopropane-fused hydoindol-5-one frameworks, each having four contiguous stereogenic centers, with three of them being fully substituted. Moreover, this method was found to provide acceptable chemical yields with promising diastereoselectivities (dr of up to ≤95 : 5) and to work with a variety of substrates.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!