2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini
Abstract
Bu çalışmada, 2-aminoasetofenon bileşiğinden başlanarak 2-,3-,4- bromo substitue azakalkon (1-3) bileşikleri sentezlendi. 1-3 Nolu bileşiklerinin katıfaz ortamında mikrodalga cihazı kullanılarak 2-, 3-, 4-bromo azaflavanon bileşikleri (4-6), sırasıyla %52, %89 ve %77 verimlerle sentezlendi. Sentezlenen bileşikler spektroskopik olarak 1Hidrojen, 13Karbon, Bağlanmış Proton Testi (APT) NMR, Fourier Dönüşümlü Kızılötesi Spektroskopisi (FT-IR) Infrared ve Sıvı kromatografi-kütle spektrometresi/kütle spektrometresi (LC-MS/MS)yöntemleriyle karakterize edildi. Sentezlenen bileşiklerin antimikrobiyal aktiviteleri 12 ayrı mikroorganizmaya (4 adet Gram pozitif, 7 adet Gram negatif ve 1 fungus) karşı disk difüzyon yöntemi kullanılarak test edildi ve minimum inhibisyon konsantrasyonu (MİK) hesaplandı. Sentezlenen azakalkon ve azaflavanon bileşikleri (1-6) test edilen mikroorganizmalar arasında en yüksek etkiyi Candida tropicalis’a karşı gösterdi. 3-Bromo azaflavanon (5) bileşiği Gram pozitif Enterococcus feacalis, Staphylococcus aureus ve fungus Candida tropicalis’a karşı etkili bulundu. Test edilen hiçbir bileşik Gram negatif bakterilere karşı etkinlik göstermedi. Sentezlenen bileşikler arasında en yüksek aktiviteyi 6.25 µg/mL’lik MIC değeri ile 2 numaralı azakalkon bileşiği Candida tropicalis’a karşı gösterdi. Ayrıca sentezlenen 1-6 nolu bileşiklerin antioksidan aktiviteleri plazmanın demir indirgeme yeteneği (FRAP) ve 1,1-Difenil-2-pikrilhidrazil kapasitesi (DPPH) yöntemlerine göre yapıldı. Antioksidant testi sonucunda, 3-bromo kalkon (173,78±1,76 ve 0,48±0,01) ve 3-bromo azaflavanon (279,05±1,77 ve 0,093±0,001) bileşiklerinin en yüksek antioksidan aktiviteye sahip oldukları görüldü.
References
- Roleiraa, M. F. F., Varelaa, C. L., Gomes, A. R., Costa, S. C., ve Silva, E.J.T. (2021). The health components of spices and herbs: The medicinal chemistry point of view. Chapter 2: Aromatic Herbs in Food Bioactive Compounds, Processing, and Applications, Pages 35-92. https://seap.taylors.edu.my/file/rems/publication/107450_8147_1.pdf.
- Sinyeue, C., Matsui, M., Oelgemöller, M., Bregier, F., Chaleix, V., Sol, V., ve Lebouvier, N. (2022). Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents. Molecules, 27, 1781-1801. https://doi.org/ 10.3390/molecules27061781
Microwave Assisted Synthesis of 2-, 3-, 4-Bromo Azaflavonones from Amino Chalcones in Solid Phase Environment, Determination of Antimicrobial and Antioxidant Activities
Abstract
In this study, 2-, 3-, 4-bromo azachalcones (1-3) were synthesized starting from the 2-aminoacetophenone. 2-, 3-, 4-bromo azaflavanones (4-6) were synthesized from the compounds 1-3 by using a microwave method in the solid phase environment with the yields of 52%, 89%, and 77%, respectively. The synthesized compounds were characterized spectroscopically ( 1H, 13C, Attached Proton Test (APT) NMR, Fouirer Transform Infrared Spectrophotometer (FT-IR) and Liquid Chromatography-Mass Spectroscopy (LC-MS/MS). The antimicrobial activities of the synthesized compounds were tested against 12 different microorganisms (4 Gram positive, 7 Gram negative and 1 fungus) using the disk diffusion method and the minimum inhibition concentration (MIC) was calculated. The synthesized azachalcone and azaflavanone compounds (1-6) showed the highest efficacy against Candida tropicalis among the microorganisms tested. 3-Bromo azaflavanone (5) was found to be effective against Gram positive Enterococcus feacalis, Staphylococcus aureus and fungus Candida tropicalis. None of the compounds showed activity against Gram-negative bacteria. Compound 2 showed the highest activity against Candida tropicalis among the tested compounds with a MIC value of 6.25 µg/mL. In addition, antioxidant activities of synthesized compounds 1- 6 were performed according to FRAP and DPPH methods. As a result of the antioxidant test, it was observed that 3-bromo chalcone (173.78±1.76 and 0.48±0.01) and 3-bromo azaflavanone (279.05±1.77 and 0.093±0.001) had shown the highest antioxidant activity
References
- Roleiraa, M. F. F., Varelaa, C. L., Gomes, A. R., Costa, S. C., ve Silva, E.J.T. (2021). The health components of spices and herbs: The medicinal chemistry point of view. Chapter 2: Aromatic Herbs in Food Bioactive Compounds, Processing, and Applications, Pages 35-92. https://seap.taylors.edu.my/file/rems/publication/107450_8147_1.pdf.
- Sinyeue, C., Matsui, M., Oelgemöller, M., Bregier, F., Chaleix, V., Sol, V., ve Lebouvier, N. (2022). Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents. Molecules, 27, 1781-1801. https://doi.org/ 10.3390/molecules27061781
Details
| Primary Language | Turkish |
|---|---|
| Subjects | Chemical Engineering |
| Journal Section | Makaleler |
| Authors | |
| Early Pub Date | June 21, 2023 |
| Publication Date | June 30, 2023 |
| Submission Date | September 13, 2022 |
| Published in Issue | Year 2023 Volume: 9 Issue: 2 |
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