Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment
Isomers of monothioureas, 2a–2d, derived from the reaction of disubstituted benzoyl isothiocyanate and dibenzylamine were synthesised and characterised by using elementary analysis CHNS and IR, 1H NMR, and 13C NMR spectroscopies. The compounds were screened for their in vitro antibacterial activity...
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| Format: | Article |
| Language: | English |
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Wiley
2018-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/9176280 |
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| author | Huda Misral Suhaila Sapari Tajudin Rahman Nazlina Ibrahim Bohari M. Yamin Siti Aishah Hasbullah |
| author_facet | Huda Misral Suhaila Sapari Tajudin Rahman Nazlina Ibrahim Bohari M. Yamin Siti Aishah Hasbullah |
| author_sort | Huda Misral |
| collection | DOAJ |
| description | Isomers of monothioureas, 2a–2d, derived from the reaction of disubstituted benzoyl isothiocyanate and dibenzylamine were synthesised and characterised by using elementary analysis CHNS and IR, 1H NMR, and 13C NMR spectroscopies. The compounds were screened for their in vitro antibacterial activity by using selected Gram-positive bacteria, and moderate inhibition activity was displayed for compound 2b with the value of inhibition zone 11 ± 0.8 mm at a concentration of 50 mg/ml. The outcomes of Lipinski’s rule of five assessment appeared to be in agreement with all compounds as they adhered to most of the rules, in which they can be preliminarily classified as active drug-like. The frontier molecular orbitals (HOMO and LUMO) for halogen-substituted 3,4-dichloro (2a) and 3,4-difluoro (2b) were also determined by applying the computational method of density functional theory (DFT) to determine their relationship as a molecular descriptor in antibacterial activities. The value of LUMO energy for compound 2b (1.8229 eV) is lower than that of compound 2a (1.8492 eV) which indicates higher antibacterial activities. |
| format | Article |
| id | doaj-art-3663ac4a8f1045af9f66bfe519bbf5a4 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-3663ac4a8f1045af9f66bfe519bbf5a42025-08-20T03:55:07ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/91762809176280Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness AssessmentHuda Misral0Suhaila Sapari1Tajudin Rahman2Nazlina Ibrahim3Bohari M. Yamin4Siti Aishah Hasbullah5School of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 Bangi, Selangor, MalaysiaIsomers of monothioureas, 2a–2d, derived from the reaction of disubstituted benzoyl isothiocyanate and dibenzylamine were synthesised and characterised by using elementary analysis CHNS and IR, 1H NMR, and 13C NMR spectroscopies. The compounds were screened for their in vitro antibacterial activity by using selected Gram-positive bacteria, and moderate inhibition activity was displayed for compound 2b with the value of inhibition zone 11 ± 0.8 mm at a concentration of 50 mg/ml. The outcomes of Lipinski’s rule of five assessment appeared to be in agreement with all compounds as they adhered to most of the rules, in which they can be preliminarily classified as active drug-like. The frontier molecular orbitals (HOMO and LUMO) for halogen-substituted 3,4-dichloro (2a) and 3,4-difluoro (2b) were also determined by applying the computational method of density functional theory (DFT) to determine their relationship as a molecular descriptor in antibacterial activities. The value of LUMO energy for compound 2b (1.8229 eV) is lower than that of compound 2a (1.8492 eV) which indicates higher antibacterial activities.http://dx.doi.org/10.1155/2018/9176280 |
| spellingShingle | Huda Misral Suhaila Sapari Tajudin Rahman Nazlina Ibrahim Bohari M. Yamin Siti Aishah Hasbullah Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment Journal of Chemistry |
| title | Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment |
| title_full | Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment |
| title_fullStr | Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment |
| title_full_unstemmed | Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment |
| title_short | Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment |
| title_sort | evaluation of novel n dibenzylcarbamothioyl benzamide derivatives as antibacterial agents by using dft and drug likeness assessment |
| url | http://dx.doi.org/10.1155/2018/9176280 |
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