2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus
An effective and greener method for the synthesis of 2-(phenyl)-4H-chromen-4-ones has been developed by reacting 2-hydroxychalcones and tert-butyl hydroperoxide (TBHP) in the presence of a base via ultrasonic irradiation. Ultrasonic irradiation is used to replace conventional energy sources in synth...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2022-01-01
|
| Series: | Current Research in Green and Sustainable Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666086521001818 |
| _version_ | 1811196924739452928 |
|---|---|
| author | Ahanthem Priyanca Devi Naveen Dhingra Uma Bhardwaj R.S. Chundawat Chetan K. Joshi Shivendra Singh Keshav Lalit Ameta |
| author_facet | Ahanthem Priyanca Devi Naveen Dhingra Uma Bhardwaj R.S. Chundawat Chetan K. Joshi Shivendra Singh Keshav Lalit Ameta |
| author_sort | Ahanthem Priyanca Devi |
| collection | DOAJ |
| description | An effective and greener method for the synthesis of 2-(phenyl)-4H-chromen-4-ones has been developed by reacting 2-hydroxychalcones and tert-butyl hydroperoxide (TBHP) in the presence of a base via ultrasonic irradiation. Ultrasonic irradiation is used to replace conventional energy sources in synthesis. In terms of energy conservation and waste reduction, ultrasonic irradiations are increasingly being used as eco-friendly, green, and clean solutions in organic processes. Antifungal activity of all the synthesized compounds was evaluated against three fungi strains. Compound 4d showed the highest activity against A. fumigatus, R. stolonifer and M. mucedo with the values of 20 ± 0.47 mm, 19 ± 0.46 mm and 22 ± 0.49 mm respectively. Compound 4d also showed highest moldock score and formed H-bond with active amino acids. Compounds bearing lipophilic electron withdrawing groups showed more potent activity compared to compounds having electron donating groups. |
| first_indexed | 2024-04-12T01:06:50Z |
| format | Article |
| id | doaj.art-9eb13e18971d4c4991b1d639a38b107f |
| institution | Directory Open Access Journal |
| issn | 2666-0865 |
| language | English |
| last_indexed | 2024-04-12T01:06:50Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Current Research in Green and Sustainable Chemistry |
| spelling | doaj.art-9eb13e18971d4c4991b1d639a38b107f2022-12-22T03:54:14ZengElsevierCurrent Research in Green and Sustainable Chemistry2666-08652022-01-0151002342-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatusAhanthem Priyanca Devi0Naveen Dhingra1Uma Bhardwaj2R.S. Chundawat3Chetan K. Joshi4Shivendra Singh5Keshav Lalit Ameta6Department of Chemistry, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, IndiaDepartment of Bioscience, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, IndiaDepartment of Bioscience, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, IndiaDepartment of Bioscience, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, IndiaDepartment of Zoology, Govt. Science College, Sikar, 332001, Rajasthan, IndiaDepartment of Chemistry, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, IndiaDepartment of Chemistry, School of Liberal Arts and Sciences, Mody University of Science and Technology, Lakshmangarh, 332311, Rajasthan, India; Corresponding author.An effective and greener method for the synthesis of 2-(phenyl)-4H-chromen-4-ones has been developed by reacting 2-hydroxychalcones and tert-butyl hydroperoxide (TBHP) in the presence of a base via ultrasonic irradiation. Ultrasonic irradiation is used to replace conventional energy sources in synthesis. In terms of energy conservation and waste reduction, ultrasonic irradiations are increasingly being used as eco-friendly, green, and clean solutions in organic processes. Antifungal activity of all the synthesized compounds was evaluated against three fungi strains. Compound 4d showed the highest activity against A. fumigatus, R. stolonifer and M. mucedo with the values of 20 ± 0.47 mm, 19 ± 0.46 mm and 22 ± 0.49 mm respectively. Compound 4d also showed highest moldock score and formed H-bond with active amino acids. Compounds bearing lipophilic electron withdrawing groups showed more potent activity compared to compounds having electron donating groups.http://www.sciencedirect.com/science/article/pii/S2666086521001818Chalcones2-(phenyl)-4H-chromen-4-onesAntifungal activityMolecular dockingChitinase |
| spellingShingle | Ahanthem Priyanca Devi Naveen Dhingra Uma Bhardwaj R.S. Chundawat Chetan K. Joshi Shivendra Singh Keshav Lalit Ameta 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus Current Research in Green and Sustainable Chemistry Chalcones 2-(phenyl)-4H-chromen-4-ones Antifungal activity Molecular docking Chitinase |
| title | 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus |
| title_full | 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus |
| title_fullStr | 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus |
| title_full_unstemmed | 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus |
| title_short | 2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus |
| title_sort | 2 phenyl 4h chromen 4 ones green synthesis characterization in vitro antifungal evaluation and molecular docking approach toward aspergillus fumigatus |
| topic | Chalcones 2-(phenyl)-4H-chromen-4-ones Antifungal activity Molecular docking Chitinase |
| url | http://www.sciencedirect.com/science/article/pii/S2666086521001818 |
| work_keys_str_mv | AT ahanthempriyancadevi 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT naveendhingra 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT umabhardwaj 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT rschundawat 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT chetankjoshi 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT shivendrasingh 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus AT keshavlalitameta 2phenyl4hchromen4onesgreensynthesischaracterizationinvitroantifungalevaluationandmoleculardockingapproachtowardaspergillusfumigatus |