New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation
Background. Benzoxazole derivatives have different biological activities. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of (3-benzoxazole-2-yl) phenylamine derivatives, 3-benzoxa...
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| Format: | Article |
| Language: | English |
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Wiley
2021-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2021/6631868 |
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| author | Mohamed A. Abdelgawad Mohammad M. Al-Sanea Mohamed A. Zaki Enas I. A. Mohamed Shabana I. Khan Babu L. Tekwani Amar G Chittiboyina Ikhlas A Khan Tarfah Al-Warhi Nada Aljaeed Ohoud J. Alotaibi Abdulsalam A. M. Alkhaldi Heba A. H. Elshemy |
| author_facet | Mohamed A. Abdelgawad Mohammad M. Al-Sanea Mohamed A. Zaki Enas I. A. Mohamed Shabana I. Khan Babu L. Tekwani Amar G Chittiboyina Ikhlas A Khan Tarfah Al-Warhi Nada Aljaeed Ohoud J. Alotaibi Abdulsalam A. M. Alkhaldi Heba A. H. Elshemy |
| author_sort | Mohamed A. Abdelgawad |
| collection | DOAJ |
| description | Background. Benzoxazole derivatives have different biological activities. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of (3-benzoxazole-2-yl) phenylamine derivatives, 3-benzoxazoloyl acetamide, and butyramide derivatives. Methods. These novel analogs were synthesized in straightforward simple chemistry without any quantitative chromatographic separations in reasonable yields. The biological evaluation of all target compounds as potential antimalarial, antileishmanial, antitrypanosomal, and antimicrobial agents was performed by various well-established cell-based methods. Results. Compounds 6d and 5a showed promising biological screening data. The amidation of 3-benzoxazolyl aniline 1 with the chloroacetyl functional group resulted in a good antimalarial activity and showed moderate inhibitory activities against leishmanial and trypanosomal spp. Moreover, chloroacetyl functionalization of benzoxazolyl aniline serves as a good early goal for constructing and synthesizing new antimicrobial and antiprotozoal agents. The molecular docking study rationalizes the relative inhibitory activity of compound 5a as an antimalarial agent with the deregulation of PfPNP activity which has emerged as a major mechanism of these targets. |
| format | Article |
| id | doaj-art-7fb32d72aa924d23adf9e407426bca42 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2021-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-7fb32d72aa924d23adf9e407426bca422025-02-03T05:58:22ZengWileyJournal of Chemistry2090-90632090-90712021-01-01202110.1155/2021/66318686631868New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological EvaluationMohamed A. Abdelgawad0Mohammad M. Al-Sanea1Mohamed A. Zaki2Enas I. A. Mohamed3Shabana I. Khan4Babu L. Tekwani5Amar G Chittiboyina6Ikhlas A Khan7Tarfah Al-Warhi8Nada Aljaeed9Ohoud J. Alotaibi10Abdulsalam A. M. Alkhaldi11Heba A. H. Elshemy12Department of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Sakakah, Aljouf 72341, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Sakakah, Aljouf 72341, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, EgyptNational Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Oxford, Mississippi 38677, USANational Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Oxford, Mississippi 38677, USANational Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Oxford, Mississippi 38677, USANational Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Oxford, Mississippi 38677, USADepartment of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh, Saudi ArabiaDepartment of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh, Saudi ArabiaDepartment of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh, Saudi ArabiaBiology Department, College of Science, Jouf University, Sakakah, Aljouf 72341, Saudi ArabiaPharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, EgyptBackground. Benzoxazole derivatives have different biological activities. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of (3-benzoxazole-2-yl) phenylamine derivatives, 3-benzoxazoloyl acetamide, and butyramide derivatives. Methods. These novel analogs were synthesized in straightforward simple chemistry without any quantitative chromatographic separations in reasonable yields. The biological evaluation of all target compounds as potential antimalarial, antileishmanial, antitrypanosomal, and antimicrobial agents was performed by various well-established cell-based methods. Results. Compounds 6d and 5a showed promising biological screening data. The amidation of 3-benzoxazolyl aniline 1 with the chloroacetyl functional group resulted in a good antimalarial activity and showed moderate inhibitory activities against leishmanial and trypanosomal spp. Moreover, chloroacetyl functionalization of benzoxazolyl aniline serves as a good early goal for constructing and synthesizing new antimicrobial and antiprotozoal agents. The molecular docking study rationalizes the relative inhibitory activity of compound 5a as an antimalarial agent with the deregulation of PfPNP activity which has emerged as a major mechanism of these targets.http://dx.doi.org/10.1155/2021/6631868 |
| spellingShingle | Mohamed A. Abdelgawad Mohammad M. Al-Sanea Mohamed A. Zaki Enas I. A. Mohamed Shabana I. Khan Babu L. Tekwani Amar G Chittiboyina Ikhlas A Khan Tarfah Al-Warhi Nada Aljaeed Ohoud J. Alotaibi Abdulsalam A. M. Alkhaldi Heba A. H. Elshemy New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation Journal of Chemistry |
| title | New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation |
| title_full | New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation |
| title_fullStr | New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation |
| title_full_unstemmed | New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation |
| title_short | New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation |
| title_sort | new benzoxazole derivatives as antiprotozoal agents in silico studies synthesis and biological evaluation |
| url | http://dx.doi.org/10.1155/2021/6631868 |
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