التفاصيل البيبلوغرافية
| العنوان: |
Synthesis and Biological Evaluation of Natural-Product-Inspired, Aminoalkyl-Substituted 1‑Benzopyrans as Novel Antiplasmodial Agents |
| المؤلفون: |
Jan-Frederik Uth (10702998), Frederik Börgel (2796301), Kirstin Lehmkuhl (1764781), Dirk Schepmann (1484284), Marcel Kaiser (41510), Valquiria A. P. Jabor (3842920), Maria Cristina Nonato (3188631), R. Luise Krauth-Siegel (549854), Thomas J. Schmidt (623656), Bernhard Wünsch (1484308) |
| سنة النشر: |
2021 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biochemistry, Microbiology, Physiology, Pharmacology, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, IC 50 values, 9 c, phenolic OH moiety, 1- Benzopyran -5-ol 8 b, aminoalcohol 19 c, nM, IC 50, LC, Novel Antiplasmodial Agents Herein, 1- aminoethyl-substituted chromenes, benzopyran |
| الوصف: |
Herein, relationships between the structures of 1-aminoethyl-substituted chromenes and their antimalarial activities were thoroughly investigated. At first, the methyl moiety in the side chain was removed to eliminate chirality. The hydrogenation state of the benzopyran system, the position of the phenolic OH moiety, and the distance of the basic amino moiety toward both aromatic rings were varied systematically. 1-Benzopyran-5-ol 8b (IC 50 = 10 nM), 1-benzopyran-7-ol 9c (IC 50 = 38 nM), and the aminoalcohol 19c (IC 50 = 17 nM) displayed antiplasmodial activity with IC 50 values below 50 nM. To identify the mechanism of action, inhibition of three key enzymes by 9c was investigated. 9c was not able to reduce the number of Plasmodia in erythrocytes of mice. This low in vivo activity was explained by fast clearance from blood plasma combined with rapid biotransformation of 9c . Three main metabolites of 9c were identified by liquid chromatography–mass spectrometry (LC–MS) methods. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| العلاقة: |
https://figshare.com/articles/journal_contribution/Synthesis_and_Biological_Evaluation_of_Natural-Product-Inspired_Aminoalkyl-Substituted_1_Benzopyrans_as_Novel_Antiplasmodial_Agents/14489382Test |
| DOI: |
10.1021/acs.jmedchem.1c00483.s001 |
| الإتاحة: |
https://doi.org/10.1021/acs.jmedchem.1c00483.s001Test |
| حقوق: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.AA27B575 |
| قاعدة البيانات: |
BASE |
