Synthesis, Characterization, Antimicrobial and Antioxidant Activities of The Homocyclotrimer Of 4-Oxo-4h-Thieno[3,4-C]Chromene-3-Diazonium Sulfate
| Autor: | Tsemeugne Joseph, Sondengam Beibam Lucas, Ngongang Ndjintchui Arnaud, Nkeng-Efouet-Alango Pepin, Kouamo Sylvian, Chouna Jean Rodolphe, Emmanuel Sopbué Fondjo, Tamokou Jean-de-Dieu, Ngouanet Doriane, Kuiate Jules-Roger, Djeukoua Dimo Kamal Sorel |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Antioxidant
Azo compounds medicine.medical_treatment Pharmaceutical Science Coumarin 010402 general chemistry 01 natural sciences Coupling reaction Article chemistry.chemical_compound Drug Discovery medicine Organic chemistry Sulfate Pharmacology Vitamin C 010405 organic chemistry Holigomer Antimicrobial 0104 chemical sciences 2-aminothiophene chemistry Homocyclotrimerization Yield (chemistry) Molecular Medicine Ferric medicine.drug SAR |
| Zdroj: | The Open Medicinal Chemistry Journal |
| ISSN: | 1874-1045 |
| Popis: | The in situ formed 4-oxo-4H-thieno[3,4-c]chromene-3-diazonium sulfate (5) in the coupling reactions involving the parent 2-aminothiophene (4) and various phenolic and arylamines' couplers, readily undergoes homocyclotrimerization at low temperature to afford in fairly good yield the first ever reported eighteen member ring heteroaromatic holigomer 6. Compound 6 was fully characterized by its elemental analysis, IR, UV-Vis, (1)H-NMR, (13)C-NMR and HRMS spectral data. The HMBC and HSQC techniques were used to ascertain the structural assignments. A comparative study on the antimicrobial and antioxidant activities of compounds 3, 4 and 6 was carried out to assess the SAR due to the transformations (from 3 to 6 via 4) on the tested compounds. It was found that compounds 6 and 4 were respectively the most active compounds against bacteria (MIC = 32-64 μg/ml) and yeasts (MIC = 16-64 μg/ml). Compound 6 also showed high radical-scavenging activities and ferric reducing power when compared with vitamin C and BHT used as reference antioxidants. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|