(2E)-3-(1-benzothiophen-2-yl)-1-(4-hydroxyphenyl)prop-2-en-1-one: Synthesis, Characterization (IR, NMR and UV-Vis) DFT Study and Antimicrobial Activity | [Journal of Chemical Society of Pakistan • 2021]

Author(s):

1. Nevin Süleymanoğlu: Vocational School of Technical Sciences, Gazi University, Ostim, Ankara, Turkey.

2. Reşat Ustabaş: Department of Mathematics and Science Education, Educational Faculty, Ondokuz Mayıs University,Kurupelit, Samsun, Turkey

3. Fatih Eyduran: Department of Chemistry, Faculty of Arts &Sciences, Adnan Menderes University, 09100, Aydın, Turkey

4. Şahin Direkel: Department of Medical Microbiology, Faculty of Medicine, Giresun University, 28100 Giresun, Turkey.

5. Yasemin Unver: Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey.

6. Nuran Kahriman: Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey.

Abstract:

Summary: In this study new chalcone derivative (2E)-3-(1-benzothiophen-2-yl)-1-(4hydroxyphenyl)prop-2-en-1-one (I), which has important pharmacological applications, was designed and synthesized. IR, NMR and LC-MS/MS empirical methods were used in order to confirm the molecular structure of the synthesized compound I. Both two tautomeric forms of the molecule were optimized by using density functional theory (DFT) method. The structural parameters formed after optimization and structural parameters obtained from similar compounds by X-ray diffraction show a good correlation. The theoretical and experimental results of IR and NMR are generally compatible, but difference arises between some values. This difference shows the existence of O-H···O type intermolecular hydrogen bond. By using its UV-Vis data, the visible absorption maximums of the molecule were analyzed. Compound I was tested against kind of Leishmania major from the point of antileishmanial activity, against kind of Candida albicans from the point of antifungal activity and against fourteen kinds of bacteria from the point of antibacterial activity in this study. The test results showed, that compound I was effective on eight kinds of bacteria and the activity strength on six bacteria among the eight was MIC: 5000 µg/mL and on the rest two kinds MIC: 1250 µg/mL. Besides, it was also found out, that compound I has MIC: 5000 µg/mL antileishmanial activity. Since bacterial and parasitic infections form serious health problems globally, compound I may be a medication candidate in future; if its antibacterial and antiparasitic effect are taken into consideration.

Page(s): 712-725

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 43, Issue: 6, Year: 2021

Keywords:

Antimicrobial activity , chalcone , DFT study , UVVis , Leishmania major , FTIRNMR

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