Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations
A series of novel riminophenazine derivatives, having ionizable alkyl substituents at N-5 and a variety of substituents on the C-3 imino nitrogen, at C-8 and on the pendant aryl group, have been designed and synthesized. Preliminary investigations into the relationship between lipophilicity, redox p...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/14/4200 |
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| author | Mpelegeng Victoria Bvumbi Chris van der Westhuyzen Edwin M. Mmutlane Andile Ngwane |
| author_facet | Mpelegeng Victoria Bvumbi Chris van der Westhuyzen Edwin M. Mmutlane Andile Ngwane |
| author_sort | Mpelegeng Victoria Bvumbi |
| collection | DOAJ |
| description | A series of novel riminophenazine derivatives, having ionizable alkyl substituents at N-5 and a variety of substituents on the C-3 imino nitrogen, at C-8 and on the pendant aryl group, have been designed and synthesized. Preliminary investigations into the relationship between lipophilicity, redox potential, and antimycobacterial activity were conducted, using the in vitro activity against <i>Mycobacterium tuberculosis</i> H<sub>37</sub>Rv, mammalian cytotoxicity, and the redox potential of the compounds determined by cyclic voltammetry as measures. Results revealed an activity “cliff” associated with C-8 substitution (<b>10l</b> and <b>10m</b>) that, along with defined redox activity, point to a new class of riminophenazines as potential anti-tuberculosis agents having reasonable activity (MIC<sub>99</sub> ~1 µM). |
| first_indexed | 2024-03-10T09:31:04Z |
| format | Article |
| id | doaj.art-fe9ef91b9abc4c87814cebc879b2bf08 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T09:31:04Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fe9ef91b9abc4c87814cebc879b2bf082023-11-22T04:30:05ZengMDPI AGMolecules1420-30492021-07-012614420010.3390/molecules26144200Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical EvaluationsMpelegeng Victoria Bvumbi0Chris van der Westhuyzen1Edwin M. Mmutlane2Andile Ngwane3Department of Chemistry, University of Johannesburg, Auckland Park 2006, South AfricaCSIR, Pharmaceutical Technologies, Pretoria 0001, South AfricaDepartment of Chemistry, University of Johannesburg, Auckland Park 2006, South AfricaDivision of Molecular Biology and Human Genetics, Department of Biomedical Sciences, Faculty of Medicine and Health Sciences, Stellenbosch University, Tygerberg 7505, South AfricaA series of novel riminophenazine derivatives, having ionizable alkyl substituents at N-5 and a variety of substituents on the C-3 imino nitrogen, at C-8 and on the pendant aryl group, have been designed and synthesized. Preliminary investigations into the relationship between lipophilicity, redox potential, and antimycobacterial activity were conducted, using the in vitro activity against <i>Mycobacterium tuberculosis</i> H<sub>37</sub>Rv, mammalian cytotoxicity, and the redox potential of the compounds determined by cyclic voltammetry as measures. Results revealed an activity “cliff” associated with C-8 substitution (<b>10l</b> and <b>10m</b>) that, along with defined redox activity, point to a new class of riminophenazines as potential anti-tuberculosis agents having reasonable activity (MIC<sub>99</sub> ~1 µM).https://www.mdpi.com/1420-3049/26/14/4200riminophenazinesalkyl substituentdrug discovery<i>Mycobacterium tuberculosis</i> |
| spellingShingle | Mpelegeng Victoria Bvumbi Chris van der Westhuyzen Edwin M. Mmutlane Andile Ngwane Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations Molecules riminophenazines alkyl substituent drug discovery <i>Mycobacterium tuberculosis</i> |
| title | Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations |
| title_full | Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations |
| title_fullStr | Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations |
| title_full_unstemmed | Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations |
| title_short | Riminophenazine Derivatives as Potential Antituberculosis Agents: Synthesis, Biological, and Electrochemical Evaluations |
| title_sort | riminophenazine derivatives as potential antituberculosis agents synthesis biological and electrochemical evaluations |
| topic | riminophenazines alkyl substituent drug discovery <i>Mycobacterium tuberculosis</i> |
| url | https://www.mdpi.com/1420-3049/26/14/4200 |
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