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Alkylaminophenols are synthetic derivatives well known for their anticancer activity. In this work, we report the antimicrobial and antioxidant activity of such compounds. A series (4,5,6) of alkylaminophenol compounds were prepared with fairly good yields by Petasis reaction. Synthesized compounds were characterized by 1 H-NMR and 13 C-NMR. The obtained compounds were tested against Gram-positive and Gram-negative bacteria. The compound 4 showed antimicrobial activity at a concentration of 10 mg/mL, while the 6 compound showed activity on S. aureus. Phenolic compounds have attracted attention due to their proximal and antioxidant activities. Since alkylaminophenols have phenolic structure, their antioxidant activity has been investigated. Thus, drug-active substances with high antioxidant capacity against diabetes, heart disease, and cancer were synthesized.

Öz Bu çalışmada; polimerleşme ve metal kompleksi oluşturabilme özelliklerine sahip amin türevi üç yeni monomer sentezlenmiştir. Sentez reaksiyonu olarak, petasis reaksiyonu seçilmiştir. Uygun optimizasyon koşullarında, herhangi bir katalizör kullanılmadan ve oldukça yüksek verimlerle hedef ürünler(monomer) elde edilmiştir. Reaksiyon verimine; sıcaklık, çözücü, atmosfer koşullarının yanısıra, substitüentlerin de etkili olduğu görülmüştür. Özellikle elektron salıcı substitüent içeren yapıların elektron çekici substitüent içeren bileşiklere göre daha istemli olduğu ve veriminin de yüksek olduğu görülmüştür. Alkilaminofenol bileşik sınıfına ait olan bu monomerlerin yapısal analizleri ise 1 H-NMR ve 13 C-NMR ile tamamlanmıştır. Sentezi yapılan monomerler, moleküler baskılanmış polimer olarak biyomoleküler tanımada kullanılabilir. Bu durum; bir çok hedef molekül için onları tanıyan uygun materyallerin elde edilmesi anlamına gelmektedir. Çalışma bu yönüyle oldukça önemlidir.

In this study, a new alkylaminophenol compound was synthesized and characterized by spectroscopic techniques (FT-IR, NMR, UV). The optimized molecular geometry and the vibrational wavenumbers were calculated using density functional theory (DFT) B3LYP/WB97XD and HF methods with 6-311++ G([Formula: see text], [Formula: see text]) basis set. Thus, theoretical data were compared within themselves before comparing with experimental data. The detailed interpretation of the vibrational spectra has been carried out by VEDA program. 1H-NMR and [Formula: see text]C-NMR chemical shifts of the compound were calculated using GIAO/IEFPCM method in CDCl3. Using time-dependent (TD-DFT) approach electronic properties such as HOMO and LUMO energies, the electronic spectrum of the title compound has been studied and reported. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Linear polarizability, anisotropic linear polarizability and hyperpolarizability values of the title compound were found to be higher than the values of the pNA compound that are used as a standard substance in the NLO analysis. Molecular electrostatic potential (MEP), the thermodynamic properties (heat capacity, entropy and enthalpy) were calculated. Also, to investigate the biological properties of the title compound, molecular docking was done with DNA(PDB ID: 414D). It has been observed that the effective interaction is hydrogen bonds.

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