Synthesis, DFT Calculations, and Molecular Docking Study of Acetohydrazide‐Based Sulfonamide Derivatives as Paraoxonase 1 Inhibitors

Author:

Arslan Gülnur12,Gökçe Başak3,Muhammed Muhammed Tilahun1,Albayrak Özlem3,Önkol Tijen2,Özçelik Azime Berna2

Affiliation:

1. Department of Pharmaceutical Chemistry Faculty of Pharmacy Suleyman Demirel University Isparta 32260 Türkiye

2. Department of Pharmaceutical Chemistry Faculty of Pharmacy Gazi University Ankara 06100 Türkiye

3. Department of Biochemistry Faculty of Pharmacy Suleyman Demirel University Isparta 32260 Türkiye

Abstract

AbstractParaoxonase 1 (PON1), an esterase linked to high‐density lipoprotein (HDL), is known to have strong antioxidant and anti‐cardiovascular properties. In this study, eleven acetohydrazide‐based sulfonamide derivatives were synthesized. All compounds were characterized by appropriate spectroscopic techniques and elemental analyses. To better understand the inhibitory properties of the new sulfonamide derivatives, theirin vitroeffects on purified PON1 enzyme activity were studied. For this purpose, PON1 was purified from human serum using simple chromatographic methods. In the experimental study, the novel compounds were found to be potent inhibitors of paraoxonase 1. The mode of binding to the enzyme, for the relatively active compounds, was investigated through molecular docking. The most active compound N′‐(naphthalen‐2‐ylsulfonyl)‐2‐(2‐oxo‐1,3‐benzothiazol‐3(2H)‐yl)acetohydrazide demonstrated the highest interaction with the enzyme. Furthermore, the electrochemical properties of these compounds were assessed through DFT (density functional theory) analysis. N′‐(naphthalen‐2‐ylsulfonyl)‐2‐(2‐oxo‐1,3‐benzothiazol‐3(2H)‐yl)acetohydrazide is anticipated to have the highest potential to take part in electron exchanges whereas N′‐[(4‐fluorophenyl)sulfonyl]‐2‐(2‐oxo‐1,3‐benzoxazol‐3(2H)‐yl)acetohydrazide is expected to have the highest chemical stability.

Publisher

Wiley

Subject

General Chemistry

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3