2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini
Yıl: 2023 Cilt: 9 Sayı: 2 Sayfa Aralığı: 465 - 476 Metin Dili: Türkçe DOI: 10.28979/jarnas.1174437 İndeks Tarihi: 10-07-2023
2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini
Öz: 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.
Anahtar Kelime: Microwave Assisted Synthesis of 2-, 3-, 4-Bromo Azaflavonones from Amino Chalcones in Solid Phase Environment, Determination of Antimicrobial and Antioxidant Activities
Öz: 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
Anahtar Kelime: Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
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| APA | YUCEL T, Fandaklı S, Demir I, YAYLI N (2023). 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. , 465 - 476. 10.28979/jarnas.1174437 |
| Chicago | YUCEL TAYYİBE BEYZA,Fandaklı Seda,Demir Ismail,YAYLI Nurettin 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. (2023): 465 - 476. 10.28979/jarnas.1174437 |
| MLA | YUCEL TAYYİBE BEYZA,Fandaklı Seda,Demir Ismail,YAYLI Nurettin 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. , 2023, ss.465 - 476. 10.28979/jarnas.1174437 |
| AMA | YUCEL T,Fandaklı S,Demir I,YAYLI N 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. . 2023; 465 - 476. 10.28979/jarnas.1174437 |
| Vancouver | YUCEL T,Fandaklı S,Demir I,YAYLI N 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. . 2023; 465 - 476. 10.28979/jarnas.1174437 |
| IEEE | YUCEL T,Fandaklı S,Demir I,YAYLI N "2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini." , ss.465 - 476, 2023. 10.28979/jarnas.1174437 |
| ISNAD | YUCEL, TAYYİBE BEYZA vd. "2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini". (2023), 465-476. https://doi.org/10.28979/jarnas.1174437 |
| APA | YUCEL T, Fandaklı S, Demir I, YAYLI N (2023). 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. Journal of advanced research in natural and applied sciences (Online), 9(2), 465 - 476. 10.28979/jarnas.1174437 |
| Chicago | YUCEL TAYYİBE BEYZA,Fandaklı Seda,Demir Ismail,YAYLI Nurettin 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. Journal of advanced research in natural and applied sciences (Online) 9, no.2 (2023): 465 - 476. 10.28979/jarnas.1174437 |
| MLA | YUCEL TAYYİBE BEYZA,Fandaklı Seda,Demir Ismail,YAYLI Nurettin 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. Journal of advanced research in natural and applied sciences (Online), vol.9, no.2, 2023, ss.465 - 476. 10.28979/jarnas.1174437 |
| AMA | YUCEL T,Fandaklı S,Demir I,YAYLI N 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. Journal of advanced research in natural and applied sciences (Online). 2023; 9(2): 465 - 476. 10.28979/jarnas.1174437 |
| Vancouver | YUCEL T,Fandaklı S,Demir I,YAYLI N 2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini. Journal of advanced research in natural and applied sciences (Online). 2023; 9(2): 465 - 476. 10.28979/jarnas.1174437 |
| IEEE | YUCEL T,Fandaklı S,Demir I,YAYLI N "2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini." Journal of advanced research in natural and applied sciences (Online), 9, ss.465 - 476, 2023. 10.28979/jarnas.1174437 |
| ISNAD | YUCEL, TAYYİBE BEYZA vd. "2-, 3-, 4-Bromo Azaflavanonların Amino Kalkonlardan Katı Faz Ortamında Mikrodalga Destekli Sentezi, Antimikrobiyal ve Antioksidan Aktivitelerinin Tayini". Journal of advanced research in natural and applied sciences (Online) 9/2 (2023), 465-476. https://doi.org/10.28979/jarnas.1174437 |
