Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

Abdou, Moaz M.; El‐Saeed, Rasha A.; Bondock, Samir

doi:10.1016/j.arabjc.2015.06.012

Cited by 79 publications

(54 citation statements)

References 267 publications

(155 reference statements)

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“…Upon consumption of the starting materials 1 and 2, after 4 h of heating (monitored by TLC), the obtained solution was neutralized with acetic acid and isolated by filtration, affording a yellow solid as the new product. It is well known that the 2,4-dioxocoumarin exist as an equilibrium mixture of their 2,4-dioxo-(a), 2-hydroxy-4-oxo-(b) and 4-hydroxy-2-oxo-(c) forms, being this latter the main component of the mixture [18]. In consequence, it is expected that its 3-acetyl derivative 1 should exist as the same type of mixtures with the tautomer 1c as the main component [19].…”

Section: Resultsmentioning

confidence: 99%

(E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one

Abonı́a

Gutiérrez

Quiroga

et al. 2018

Molbank

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The coumarinyl-quinolinylchalcone hybrid (E)-3-[3-(2-butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one 3b was prepared in good yield from a Claisen-Schmidt condensation reaction between 3-acetyl-4-hydroxy-2H-chromen-2-one 1 and 2-butoxyquinoline-3-carbaldehyde 2 in methanol at reflux and catalyzed by KOH pellets. The structure of the synthesized compound 3b was fully confirmed by FTIR-ATR, (1D and 2D) NMR experiments, EIMS and elemental analysis.

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Section: Resultsmentioning

confidence: 99%

(E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one

Abonı́a

Gutiérrez

Quiroga

et al. 2018

Molbank

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“…4-hydroxycoumarin is a structural motif present in various pharmaceuticals and clinical drugs like warfarin, etc. [43,44]. Based on their unique pharmacological properties, Praveen et al speculated that combining the structural characteristics of both spirooxindole and 4-hydroxycoumarin moieties by a hybrid pharmacophore approach could remarkably enhance the biological activity.…”

Section: Spirooxindole Tetrahydrofurans and 4h-pyransmentioning

confidence: 99%

The Development of Biologically Important Spirooxindoles as New Antimicrobial Agents

Yang

Zhu

Liao

et al. 2018

CMC

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This review highlights the importance of spirooxindoles as potential antimicrobial agents. The antimicrobial activity of spirooxindoles against different types of bacteria is less studied, mainly centering on primary antimicrobial assessment, some of these compounds have showed interesting antimicrobial activity. However, the current study is only limited to primary antimicrobial assessment, no detailed modes of action are investigated.

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“…Further, there is growing interest in the development of synthetic strategy for furo [3,2-c]pyran-4-ones and furo [3,2-c]chromen-4-ones. Many methods have been successfully advanced for the synthesis of furo [3,2-c]pyran-4-ones and furo [3,2-c]chromen-4-ones utilizing different typical procedures [21][22][23][24][25][26][27]. Therefore, herein we report a simple and straight forward synthesis of furo [3,2-c]pyran-4-ones and furo [3,2-c]chromen-4-ones from readily available versatile materials, dehydroacetic acid and 4-hydroxycoumarin, respectively.…”

Section: Introductionmentioning

confidence: 99%

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

Rani¹,

Kamra²,

Thakral³

et al. 2021

Preprint

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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.

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Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

Abstract: This review aims to document the publications concerning 4-hydroxycoumarin, its synthesis, chemical reactivity and reactions during the period from 1996 up to now.

Cited by 79 publications

References 267 publications

(E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one

(E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one

The Development of Biologically Important Spirooxindoles as New Antimicrobial Agents

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

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