Design and synthesis of highly oxygenated furo[3,2-c]pyran-4-ones and furo[3,2-c]chromen-4-ones scaffold as potential anticancer and antimicrobial agent

2021 · doi:10.3762/bxiv.2021.37.v1
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Researchers synthesized highly oxygenated furo[3,2-c]pyran-4-ones and furo[3,2-c]chromen-4-ones scaffolds using a simple one-pot reaction from dehydroacetic acid and 3-acetyl-4-hydroxycoumarin. The resulting compounds were evaluated for in vitro anticancer activity against colon, lung, prostate, and breast cancer cell lines, as well as antimicrobial potential against various bacterial and fungal strains. Several derivatives demonstrated significant cytotoxicity, particularly compound 9d against prostate PC-3 cells with an IC50 of 3.8 µM, while others showed superior antifungal efficacy compared to standard drugs. This paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

Synthesis of a number of highly oxygenated furo[3,2-c]pyran-4-one ( 4 , 5 ) and furo[3,2-c]chromen-4-one ( 8 , 9 ) has been accomplished by a simple one pot reaction from easily available versatile starting materials - dehydroacetic acid and 3-acetyl-4-hydroxycoumarin. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity ( in vitro ) against three Colon (HCT-116, SW-620, HT-24), Lung (A-549), Prostate-(PC-3), Breast-(MCF-7) cell lines. Compounds 5a , 9d , 9f showed good activity against breast MCF-7 cancer cell line having IC 50 values 6.9, 2.8, 5.3 µM, respectively. Out of these compound 9d showed better activity against prostate PC-3 cell line with IC 50 value 3.8 µM. The synthesized compounds were also studied for potential antibacterial activity ( in vitro ) using different strains of bacteria ( Bacillus subtilis and Staphylococcus aureus -Gram-positive, and Escherichia coli - Gram negative) as well as fungal strains ( Aspergillus niger and Candida albicans ) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The outcome of the antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis while 5h showed excellent and 5i and 9b showed better activity against E. coli . The compounds 5c - 5e displayed excellent activity against C. albicans and A. niger than Fluconazole.
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Materials

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry Synthesis of a number of highly oxygenated furo[3,2-c]pyran-4-one (4, 5) and furo[3,2-c]chromen-4-one (8, 9) has been accomplished by a simple one pot reaction from easily available versatile starting materials - dehydroacetic acid and 3-acetyl-4-hydroxycoumarin. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity (in vitro) against three Colon (HCT-116, SW-620, HT-24), Lung (A-549), Prostate-(PC-3), Breast-(MCF-7) cell lines. Compounds 5a, 9d, 9f showed good activity against breast MCF-7 cancer cell line having IC50 values 6.9, 2.8, 5.3 µM, respectively. Out of these compound 9d showed better activity against prostate PC-3 cell line with IC50 value 3.8 µM. The synthesized compounds were also studied for potential antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive, and Escherichia coli- Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The outcome of the antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis while 5h showed excellent and 5i and 9b showed better activity against E. coli. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

Keywords

3-Acetyl-4-hydroxycoumarin, anticancer, antimicrobial, dehydroacetic acid, furo[3,2-c]pyrone, furo[3,2-c]chromen-4-one | Format: PDF | Size: 2.6 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Rani, S.; Kamra, N.; Thakral, S.; Kumar, D.; Singh, A.; Sangwan, P. L.; Singh, S. K. Beilstein Arch. 2021, 202137. doi:10.3762/bxiv.2021.37.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2021 Rani et al.; licensee Beilstein-Institut. This is an open access work under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

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