Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds
A series of 4-amino-5-substituted-thiophene derivatives 3, 5 and 7, along with their corresponding thieno[3,2-d]pyrimidine compounds 4, 6 and 8, were synthesized and characterized. DFT calculations were utilized to determine frontier orbitals energies. The data showed that the compounds have low HOM...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2023-12-01
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| Series: | Journal of Taibah University for Science |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/16583655.2023.2164993 |
| _version_ | 1797215171018489856 |
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| author | Aisha Hossan Mansoor Alsahag Ali Alisaac Majid A. Bamaga Adel I. Alalawy Nashwa M. El-Metwaly |
| author_facet | Aisha Hossan Mansoor Alsahag Ali Alisaac Majid A. Bamaga Adel I. Alalawy Nashwa M. El-Metwaly |
| author_sort | Aisha Hossan |
| collection | DOAJ |
| description | A series of 4-amino-5-substituted-thiophene derivatives 3, 5 and 7, along with their corresponding thieno[3,2-d]pyrimidine compounds 4, 6 and 8, were synthesized and characterized. DFT calculations were utilized to determine frontier orbitals energies. The data showed that the compounds have low HOMO and LUMO energies, where 4-methyl thienopyrimidine 4 and 5 have the lowest values. According to results of antibacterial activity against two distinct strains of Gram positive and negative bacteria through two different concentrations (0.5 and 1.0 mg/mL). Compounds 6 and 8 show (IC50 = 43.53±3.26, 45.64±3.42 and 39.72±2.98, 42.57±3.19 mg/mL) good action toward S. aureus compared to chloramphenicol. Meanwhile, cytotoxic activity for inspected derivatives was evaluated toward three cancer cell lines. The investigated thiophene derivatives 4, 6 and 7 were displayed potent cytotoxic effectiveness (14.53±0.54, 11.17±0.42, 16.76±0.63 μM) against MCF-7 versus 5-fluorouracil as standard drug. In addition, the theoretical study such as molecular docking was stimulated. |
| first_indexed | 2024-03-10T08:13:50Z |
| format | Article |
| id | doaj.art-9b614e68e4a14a5e965b63662ffb3e73 |
| institution | Directory Open Access Journal |
| issn | 1658-3655 |
| language | English |
| last_indexed | 2024-04-24T11:25:49Z |
| publishDate | 2023-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Taibah University for Science |
| spelling | doaj.art-9b614e68e4a14a5e965b63662ffb3e732024-04-10T20:17:48ZengTaylor & Francis GroupJournal of Taibah University for Science1658-36552023-12-0117110.1080/16583655.2023.2164993Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compoundsAisha Hossan0Mansoor Alsahag1Ali Alisaac2Majid A. Bamaga3Adel I. Alalawy4Nashwa M. El-Metwaly5Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi ArabiaDepartment of Laboratory Medicine, Faculty of Applied Medical Sciences, Albaha University, Al Bahah, Saudi ArabiaDepartment of Laboratory Medicine, Faculty of Applied Medical Sciences, Albaha University, Al Bahah, Saudi ArabiaDepartment of Environmental and Health Research, The Custodian of The Two Holy Mosques Institute of Hajj and Umrah Research, Umm Al-Qura University, Makkah, Saudi ArabiaDepartment of Biochemistry, Faculty of Science, University of Tabuk, Tabuk, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al Qura University, Makkah, Saudi ArabiaA series of 4-amino-5-substituted-thiophene derivatives 3, 5 and 7, along with their corresponding thieno[3,2-d]pyrimidine compounds 4, 6 and 8, were synthesized and characterized. DFT calculations were utilized to determine frontier orbitals energies. The data showed that the compounds have low HOMO and LUMO energies, where 4-methyl thienopyrimidine 4 and 5 have the lowest values. According to results of antibacterial activity against two distinct strains of Gram positive and negative bacteria through two different concentrations (0.5 and 1.0 mg/mL). Compounds 6 and 8 show (IC50 = 43.53±3.26, 45.64±3.42 and 39.72±2.98, 42.57±3.19 mg/mL) good action toward S. aureus compared to chloramphenicol. Meanwhile, cytotoxic activity for inspected derivatives was evaluated toward three cancer cell lines. The investigated thiophene derivatives 4, 6 and 7 were displayed potent cytotoxic effectiveness (14.53±0.54, 11.17±0.42, 16.76±0.63 μM) against MCF-7 versus 5-fluorouracil as standard drug. In addition, the theoretical study such as molecular docking was stimulated.https://www.tandfonline.com/doi/10.1080/16583655.2023.21649934-AminothiophenethienopyrimidineMulliken’s chargesantimicrobialHCT-116molecular docking |
| spellingShingle | Aisha Hossan Mansoor Alsahag Ali Alisaac Majid A. Bamaga Adel I. Alalawy Nashwa M. El-Metwaly Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds Journal of Taibah University for Science 4-Aminothiophene thienopyrimidine Mulliken’s charges antimicrobial HCT-116 molecular docking |
| title | Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds |
| title_full | Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds |
| title_fullStr | Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds |
| title_full_unstemmed | Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds |
| title_short | Synthesis, molecular modelling and biological evaluation of new 4-aminothiophene and thienopyrimidine compounds |
| title_sort | synthesis molecular modelling and biological evaluation of new 4 aminothiophene and thienopyrimidine compounds |
| topic | 4-Aminothiophene thienopyrimidine Mulliken’s charges antimicrobial HCT-116 molecular docking |
| url | https://www.tandfonline.com/doi/10.1080/16583655.2023.2164993 |
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