A new synthesis of 2-aroylbenzothiazoles iodine-promoted domino transformations of anilines, acetophenones, and elemental sulfur was demonstrated. The highlights of this tandem synthesis are (1) easily available anilines and acetophenones as feedstock; (2) transition metal-free conditions; (3) inexpensive, nontoxic, easy handling, and abundant elemental sulfur as a building block. This synthetic strategy would complement the existing methods in the synthesis of this important heterocyclic scaffold. To our best knowledge, the formation of 2-aroylbenzothiazoles from simple anilines, acetophenones, and elemental sulfur was not previously reported in the literature.
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http://dx.doi.org/10.1039/d0ra01750g | DOI Listing |
Chem Commun (Camb)
January 2025
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
We report a cascade synthesis of indole-fused benzodiazepines by the photocatalyzed addition of phenacyl radical, generated from α-acetoxy acetophenone, to 2-(3-methyl-1-indol-1-yl)aniline, and subsequent cyclodehydration. A range of indole-fused benzodiazepines were obtained from readily available substrates.
View Article and Find Full Text PDFUltrasonics
January 2025
Department of Chemistry, University of Calicut, Calicut University (PO), Malappuram DT, Kerala - 673635, India. Electronic address:
Biomolecules
December 2023
Department of Molecular Pathology, Graduate School of Medicine, Osaka Metropolitan University, 1-4-3 Asahi-machi, Abeno-ku, Osaka 545-8585, Japan.
Occupational exposure to aromatic amines (AAs) is an important risk factor for urinary bladder cancer. This study aimed to evaluate the toxicity of AAs and analyze the carcinogenic mechanisms in rat bladder by comprehensive analysis of DNA adducts (DNA adductome). DNA was extracted from the bladder epithelia of rats treated with AAs, including acetoacet--toluidine (AAOT) and -toluidine (OTD), and adductome analysis was performed.
View Article and Find Full Text PDFInt J Mol Sci
November 2023
Laboratory of Drug Targets Histopathology, Institute of Cardiology, Lithuanian University of Health Sciences, Sukilėlių pr. 13, 50162 Kaunas, Lithuania.
The title compounds were synthesized by the reaction of 5-oxo-1-(4-(phenylamino)phenyl)pyrrolidine-3-carbohydrazide with various aldehydes bearing aromatic and heterocyclic moieties and acetophenones, and their cytotoxicity was tested via MTT assay against human triple-negative breast cancer MDA-MB-231, human melanoma IGR39, human pancreatic carcinoma Panc-1, and prostate cancer cell line PPC-1. Furthermore, the selectivity of compounds towards cancer cells compared to fibroblasts was also investigated. Four compounds were identified as the most promising anticancer agents out of a series of pyrrolidinone-hydrazone derivatives bearing a diphenylamine moiety.
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