Efficient Microwave‐Assisted Synthesis, In Vitro Antimicrobial Evaluation of Furo[3,2‐c]pyrones and Furo[3,2‐c]coumarins along with Molecular Docking Studies

Rani, Suman; Kamra, Nisha; Kumar, Devinder; Kumar, Ashwani

doi:10.1002/slct.202003648

Cited by 5 publications

(1 citation statement)

References 31 publications

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“…[19] Further, there is growing interest in the development of synthetic strategy for furo [3,2-c]pyran/chromen-4-ones and subsequently 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. [20][21][22][23][24][25][26][27] Therefore, in continuation of our previous work, [28] we planned to synthesize highly oxygenated furo [3,2-c]pyran/chromen-4-ones (oxygen-containing oxygen heterocycles) from dehydroacetic acid and 4-hydroxycoumarin or their chalcone, respectively, utilizing simple protocol. The synthesized compounds were characterized and screened for cytotoxicity as well as antimicrobial activities.…”

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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 anticancer and antimicrobial agents

Rani

Kumar

Kamra

et al. 2021

Journal of Heterocyclic Chem

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Synthesis of a number of highly oxygenated furo [3,2-c]pyran/chromen-4-one has been accomplished by one-pot reaction from easily available dehydroacetic acid/3-acetyl-4-hydroxycoumarin or their chalcones and α-bromoketones. 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. Of these compounds, 9d showed better activity against prostate PC-3 cell line with IC 50 value 3.8 μM. The synthesized compounds were also studied for antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive and Escherichia coli, Pseudomonas aeruginosa -Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. 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. Compounds 5d and 5e showed promising activity against P. aeruginosa. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

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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 anticancer and antimicrobial agents

Rani

Kumar

Kamra

et al. 2021

Journal of Heterocyclic Chem

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Synthesis of Spiro[benzo[b]thiophene‐2(3H),1′‐cyclopropan]‐3‐ones via Domino Reaction Between Thioaurones and Sulfur Ylides

Dai

Hao

et al. 2021

Asian J Org Chem

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A Cs 2 CO 3 -promoted domino reaction between thioaurones and sulfur ylides was developed. A series of spiro [benzo[b]thiophene-2(3H),1'-cyclopropan]-3-ones were obtained in good-to-high yields. The present domino strategy tolerated both electron-withdrawing and electron-donating groups on both thioaurones and sulfur ylides. The reaction mechanism and the origin of the observed diastereoselectivity were investigated.Scheme 4. The proposed mechanism and the stereoselectivity, along with the computed relative free-energy values (given in square brackets, kcal/mol) by DFT calculations.

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Coumarin Derivatives: Microwave Synthesis and Biological Properties—A Review

Habibi,

Talbi,

Hamri

et al. 2024

Journal of Heterocyclic Chem

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Many molecules called coumarins with very varied biological activities and widely used in the food, pharmaceutical, cosmetic, and medical industries. Their structure has a significant impact on their biological activity and their possible applications. Advanced synthesis frequently leads to an increase in the production of various chemical wastes. The amount of hazardous organic substances used and produced is reduced by the application of environmentally friendly synthesis techniques. Numerous techniques are employed in green chemistry, including the use of ionic liquids and deep eutectic solvents, solvent‐free synthesis, mechanical synthesis, multicomponent reactions, ultrasound, and microwaves. These green synthesis techniques have been successfully applied to all common condensation reactions for the synthesis of coumarin, including the Perkin, Knoevenagel, Pechmann, Kostanecki‐Robinson, and Reformansky reactions. These methods not only reduce the use and production of toxic chemicals, but also improve the yield, purity, and energy consumption of the product. This review summarizes the methods of microwave synthesis of coumarin derivatives, as well as their biological activities.

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Efficient Microwave‐Assisted Synthesis, In Vitro Antimicrobial Evaluation of Furo[3,2‐c]pyrones and Furo[3,2‐c]coumarins along with Molecular Docking Studies

Cited by 5 publications

References 31 publications

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

Synthesis of Spiro[benzo[b]thiophene‐2(3H),1′‐cyclopropan]‐3‐ones via Domino Reaction Between Thioaurones and Sulfur Ylides

Coumarin Derivatives: Microwave Synthesis and Biological Properties—A Review

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