Synthesis, Characterization, Theoretical Analyses, and Investigation of Their Biological Activities of Acetovanillone-Derived Novel Benzyl Ethers

Küçük Resim Yok

Tarih

2022

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Taylor & Francis Ltd

Erişim Hakkı

info:eu-repo/semantics/closedAccess

Özet

In this study, acetovanillone-derived novel benzyl ethers were synthesized as target compounds. For the synthesis of these target compounds, ketone derivatives (3a-b) were synthesized as the starting compounds. Compounds 4a-b, which are alcohol derivatives, were then synthesized from the reduction of these ketone derivatives. In the last stage of the synthesis study, benzyl ether derivatives (6a-h, 7a-h), the target compounds containing acetovanillone, were synthesized from the reaction of the alcohol derivatives (4a-b) with various benzyl halides (5a-h). The structures of the synthesized compounds were characterized by various spectroscopic methods (FT-IR, H-1 NMR, C-13 NMR, mass spectrometry, and elemental analysis). In vitro antileishmanial and antibacterial activity tests were then performed for all synthesized compounds. Biological activity tests showed that while only a few of the compounds had antileishmanial activity, most had antibacterial activity. In addition, the ADME parameters, pharmacokinetic properties, and drug-like nature of all compounds were theoretically investigated using the SwissADME webserver. Finally, molecular docking simulations were carried out to support in vitro investigations and evaluate the inhibition effect of the synthesized compounds on the 3IW2 (Mycobacterium tuberculosis (Mtb) Cyp125; Pdb ID: 3IW2) receptor structure. Also, possible binding sites of some compounds with high affinity to Mtb Cyp125 according to docking results were identified.

Açıklama

Anahtar Kelimeler

Acetovanillone, benzyl ethers, biological activity, ADME, molecular docking simulation

Kaynak

Polycyclic Aromatic Compounds

WoS Q Değeri

Q3

Scopus Q Değeri

Q3

Cilt

42

Sayı

8

Künye