Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations
Given the importance of carbohydrate-based drugs, this study focused on the synthesis of five novel analogs (3–7) of methyl 4,6-O-benzylidene-α-D-glucopyranoside (2, MBDG). In vitro antimicrobial screening revealed that these MBDG derivatives possess promising antifungal activity against Aspergillus...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-06-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S266702242400330X |
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| author | Sarkar M.A. Kawsar Md. Ahad Hossain Mohammad I. Hosen Mehul P. Parmar Subham G. Patel Hitendra M. Patel Imtiaj Hasan Suvro Biswas Md. Abu Saleh |
| author_facet | Sarkar M.A. Kawsar Md. Ahad Hossain Mohammad I. Hosen Mehul P. Parmar Subham G. Patel Hitendra M. Patel Imtiaj Hasan Suvro Biswas Md. Abu Saleh |
| author_sort | Sarkar M.A. Kawsar |
| collection | DOAJ |
| description | Given the importance of carbohydrate-based drugs, this study focused on the synthesis of five novel analogs (3–7) of methyl 4,6-O-benzylidene-α-D-glucopyranoside (2, MBDG). In vitro antimicrobial screening revealed that these MBDG derivatives possess promising antifungal activity against Aspergillus niger and moderate antibacterial activity. Compound 4 exhibited an MIC of 0.68–2.7 mg/mL and an MBC of 1.35–5.4 mg/mL against five different bacterial strains. The insertion of various acyl groups, particularly (CH3(CH2)3CO-) and (CH3(CH2)4CO-) at the second and third positions of MBDG (2), increased the antimicrobial effectiveness. Compound 6 was found to reduce EAC (Ehrlich ascites carcinoma) cell proliferation by 30.17% at 500 μg/mL, with an IC50 value of 852.47 μg/mL. Furthermore, frontier molecular orbital (FMO) and molecular electrostatic potential (MEP) analyses were conducted to investigate the physicochemical properties and relative reactivities of the newly synthesized MBDGs. Molecular docking analysis revealed that compounds 4 and 5 bind efficiently with binding affinities of -7.2 kcal/moL and -5.7 kcal/moL against Bacillus subtilis and A. niger, respectively, compared with the standard drug azithromycin. The stability of the protein‒ligand complexes were ascertained via MMPBSA binding free energy calculations and molecular dynamics (MD) simulations. These findings demonstrate that compounds 4 and 5 may be useful antimicrobial medications. An in silico ADMET assay was employed to evaluate the pharmacological and toxicological properties of the MBDGs. |
| format | Article |
| id | doaj-art-6ad253c556bf4e62a8331f21506c100f |
| institution | Kabale University |
| issn | 2667-0224 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Chemical Physics Impact |
| spelling | doaj-art-6ad253c556bf4e62a8331f21506c100f2025-08-20T03:45:28ZengElsevierChemical Physics Impact2667-02242025-06-011010078610.1016/j.chphi.2024.100786Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigationsSarkar M.A. Kawsar0Md. Ahad Hossain1Mohammad I. Hosen2Mehul P. Parmar3Subham G. Patel4Hitendra M. Patel5Imtiaj Hasan6Suvro Biswas7Md. Abu Saleh8Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh; Corresponding author.Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, BangladeshLaboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, BangladeshDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388120, Gujarat, IndiaDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388120, Gujarat, IndiaDepartment of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388120, Gujarat, IndiaDepartment of Microbiology, University of Rajshahi, Rajshahi 6205, Bangladesh; Department of Biochemistry and Molecular Biology, University of Rajshahi, Rajshahi 6205, BangladeshMicrobiology Laboratory, Department of Genetic Engineering and Biotechnology, University of Rajshahi, Rajshahi 6205, BangladeshMicrobiology Laboratory, Department of Genetic Engineering and Biotechnology, University of Rajshahi, Rajshahi 6205, BangladeshGiven the importance of carbohydrate-based drugs, this study focused on the synthesis of five novel analogs (3–7) of methyl 4,6-O-benzylidene-α-D-glucopyranoside (2, MBDG). In vitro antimicrobial screening revealed that these MBDG derivatives possess promising antifungal activity against Aspergillus niger and moderate antibacterial activity. Compound 4 exhibited an MIC of 0.68–2.7 mg/mL and an MBC of 1.35–5.4 mg/mL against five different bacterial strains. The insertion of various acyl groups, particularly (CH3(CH2)3CO-) and (CH3(CH2)4CO-) at the second and third positions of MBDG (2), increased the antimicrobial effectiveness. Compound 6 was found to reduce EAC (Ehrlich ascites carcinoma) cell proliferation by 30.17% at 500 μg/mL, with an IC50 value of 852.47 μg/mL. Furthermore, frontier molecular orbital (FMO) and molecular electrostatic potential (MEP) analyses were conducted to investigate the physicochemical properties and relative reactivities of the newly synthesized MBDGs. Molecular docking analysis revealed that compounds 4 and 5 bind efficiently with binding affinities of -7.2 kcal/moL and -5.7 kcal/moL against Bacillus subtilis and A. niger, respectively, compared with the standard drug azithromycin. The stability of the protein‒ligand complexes were ascertained via MMPBSA binding free energy calculations and molecular dynamics (MD) simulations. These findings demonstrate that compounds 4 and 5 may be useful antimicrobial medications. An in silico ADMET assay was employed to evaluate the pharmacological and toxicological properties of the MBDGs.http://www.sciencedirect.com/science/article/pii/S266702242400330XMBDG derivativesAntimicrobial studyAnticancer studyMolecular dockingMD simulationIn silico ADMET prediction |
| spellingShingle | Sarkar M.A. Kawsar Md. Ahad Hossain Mohammad I. Hosen Mehul P. Parmar Subham G. Patel Hitendra M. Patel Imtiaj Hasan Suvro Biswas Md. Abu Saleh Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations Chemical Physics Impact MBDG derivatives Antimicrobial study Anticancer study Molecular docking MD simulation In silico ADMET prediction |
| title | Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations |
| title_full | Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations |
| title_fullStr | Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations |
| title_full_unstemmed | Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations |
| title_short | Novel benzylidene derivatives: Synthesis and their antimicrobial and anticancer studies and in silico investigations |
| title_sort | novel benzylidene derivatives synthesis and their antimicrobial and anticancer studies and in silico investigations |
| topic | MBDG derivatives Antimicrobial study Anticancer study Molecular docking MD simulation In silico ADMET prediction |
| url | http://www.sciencedirect.com/science/article/pii/S266702242400330X |
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