In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents
Abstract A series of novel diphenylamine fluorinated chalcone derivatives (B1–B10) were synthesized and characterized using 1H and 13C NMR, IR, and MS, and purity was determined using HPLC. The compounds were evaluated for their antimicrobial, antimalarial, and anticancer activities, with Chloramphe...
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Nature Portfolio
2025-05-01
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| Online Access: | https://doi.org/10.1038/s41598-025-04073-6 |
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| author | Aviral Shah Kathan Desai Ajaykumar Bhanusali Shikha Agrawal Khushbu Patel Nilesh Naik Anuj Thakar Hem Naik Dilip Kanjariya Naved Malek Smita Jauhari Yogesh Kadam Bhavesh Patel Ankit B. Shah |
| author_facet | Aviral Shah Kathan Desai Ajaykumar Bhanusali Shikha Agrawal Khushbu Patel Nilesh Naik Anuj Thakar Hem Naik Dilip Kanjariya Naved Malek Smita Jauhari Yogesh Kadam Bhavesh Patel Ankit B. Shah |
| author_sort | Aviral Shah |
| collection | DOAJ |
| description | Abstract A series of novel diphenylamine fluorinated chalcone derivatives (B1–B10) were synthesized and characterized using 1H and 13C NMR, IR, and MS, and purity was determined using HPLC. The compounds were evaluated for their antimicrobial, antimalarial, and anticancer activities, with Chloramphenicol, Griseofulvin, and 5-Fluorouracil serving as standard reference drugs. Notably, B6 exhibited excellent antifungal activity, comparable to that of the standard drug Griseofulvin. Compounds B3 and B5 showed strong antimalarial effects against Plasmodium falciparum. Both B3 and B5 exhibit substantial cytotoxicity against HeLa cells, with IC50 values of 24.53 µg/ml for B5 and 32.42 µg/ml for B3. These results clearly demonstrate that both compounds outperform the standard drug 5-Fluorouracil, establishing their strong potential as effective alternatives in cancer therapy. Molecular docking studies revealed that B3 and B6 effectively interacted with the active site of Falcilysin, while B5 and B7 showed favourable binding to proteins 6GUE and 2 × 7 F. Molecular dynamics simulations confirmed the stability of B3 and B6 with P. falciparum, while B5 and B3 exhibited promising interactions with 6GUE and 2X7F. These results suggest that compounds B3 and B5 are potential lead candidates for developing novel antimicrobial, antimalarial, and anticancer therapies. |
| format | Article |
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| institution | DOAJ |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-05-01 |
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| spelling | doaj-art-3aba680a90cb4698809ee45a608f6ad92025-08-20T03:16:33ZengNature PortfolioScientific Reports2045-23222025-05-0115111910.1038/s41598-025-04073-6In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agentsAviral Shah0Kathan Desai1Ajaykumar Bhanusali2Shikha Agrawal3Khushbu Patel4Nilesh Naik5Anuj Thakar6Hem Naik7Dilip Kanjariya8Naved Malek9Smita Jauhari10Yogesh Kadam11Bhavesh Patel12Ankit B. Shah13Chemistry Department, Bhagwan Mahavir UniversityChemistry Department, Bhagwan Mahavir UniversityChemistry Department, Bhagwan Mahavir UniversityChemistry Department, Bhagwan Mahavir UniversityChemistry Department, Bhagwan Mahavir UniversityAnupam Rasayan India Limited, GIDCAnupam Rasayan India Limited, GIDCDepartment of Chemistry, S.V. National Institute of TechnologyDepartment of Chemistry, S.V. National Institute of TechnologyDepartment of Chemistry, S.V. National Institute of TechnologyDepartment of Chemistry, S.V. National Institute of TechnologyDepartment of Chemistry, School of Science and Technology, Vanita Vishram Women’s UniversityDepartment of Chemistry, Sir P. T. Sarvajanik College of ScienceChemistry Department, Bhagwan Mahavir UniversityAbstract A series of novel diphenylamine fluorinated chalcone derivatives (B1–B10) were synthesized and characterized using 1H and 13C NMR, IR, and MS, and purity was determined using HPLC. The compounds were evaluated for their antimicrobial, antimalarial, and anticancer activities, with Chloramphenicol, Griseofulvin, and 5-Fluorouracil serving as standard reference drugs. Notably, B6 exhibited excellent antifungal activity, comparable to that of the standard drug Griseofulvin. Compounds B3 and B5 showed strong antimalarial effects against Plasmodium falciparum. Both B3 and B5 exhibit substantial cytotoxicity against HeLa cells, with IC50 values of 24.53 µg/ml for B5 and 32.42 µg/ml for B3. These results clearly demonstrate that both compounds outperform the standard drug 5-Fluorouracil, establishing their strong potential as effective alternatives in cancer therapy. Molecular docking studies revealed that B3 and B6 effectively interacted with the active site of Falcilysin, while B5 and B7 showed favourable binding to proteins 6GUE and 2 × 7 F. Molecular dynamics simulations confirmed the stability of B3 and B6 with P. falciparum, while B5 and B3 exhibited promising interactions with 6GUE and 2X7F. These results suggest that compounds B3 and B5 are potential lead candidates for developing novel antimicrobial, antimalarial, and anticancer therapies.https://doi.org/10.1038/s41598-025-04073-6Fluorinated diphenylamine ChalconesIn vitro biological evaluationMethoxy functional group (-OCH3)In Silico study |
| spellingShingle | Aviral Shah Kathan Desai Ajaykumar Bhanusali Shikha Agrawal Khushbu Patel Nilesh Naik Anuj Thakar Hem Naik Dilip Kanjariya Naved Malek Smita Jauhari Yogesh Kadam Bhavesh Patel Ankit B. Shah In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents Scientific Reports Fluorinated diphenylamine Chalcones In vitro biological evaluation Methoxy functional group (-OCH3) In Silico study |
| title | In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| title_full | In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| title_fullStr | In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| title_full_unstemmed | In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| title_short | In vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| title_sort | in vitro and in silico evaluation of fluorinated diphenylamine chalcone derivatives as potential antimalarial and anticancer agents |
| topic | Fluorinated diphenylamine Chalcones In vitro biological evaluation Methoxy functional group (-OCH3) In Silico study |
| url | https://doi.org/10.1038/s41598-025-04073-6 |
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