Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages

Shrestha Aarajana; Oh Hye Jin; Kim Mi Jin; Pun Nirmala Tilija; Magar Til Bahadur Thapa; Bist Ganesh; Choi Hongseok; Park Pil-Hoon; Lee Eung-Seok

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Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages

机译：含有2-苄基-1-吲哚酮衍生物的卤素的设计，合成和结构 - 活性研究抑制LPS刺激的ROS型ROS生产中的RAP 264.7巨噬细胞

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As a continuous effort to discover new potential anti-inflammatory agents, we systematically designed and synthesized sixty-one 2-benzylidene-1-indanone derivatives with structural modification of chalcone, and evaluated their inhibitory activity on LPS-stimulated ROS production in RAW 264.7 macrophages. Systematic structure-activity relationship study revealed that hydroxyl group in C-5, C-6, or C-7 position of indanone moiety, and ortho-, meta-, or para-fluorine, trifluoromethyl, trifluoromethoxy, and bromine functionalities in phenyl ring are important for inhibition of ROS production in LPS-stimulated RAW 264.7 macrophages. Among all the tested compounds, 6-hydroxy-2-(2-(trifluoromethoxy) benzylidene)-2,3-dihydro-1H-inden-1-one (compound 44) showed the strongest inhibitory activity of ROS production. Further studies on the mode of action revealed that compound 44 potently suppressed LPS-stimulated ROS production via modulation of NADPH oxidase. The findings of this work could be useful to design 2-benzylidene-indanone based lead compounds as novel anti-inflammatory agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

机译：作为发现新的潜在抗炎剂的持续努力，我们系统地设计和合成了具有Chalcone的结构改性的六十一苄基-1-吲哚酮衍生物，并在原始264.7巨噬细胞中评价其对LPS刺激的ROS生产的抑制活性。系统的结构 - 活性关系研究表明，苯环的C-5，C-6或C-7位的羟基，C-6或C-7位位置，苯基环中的三氟甲基，三氟甲氧基和溴官能团对于LPS刺激的原始264.7巨噬细胞抑制ROS产生是重要的。在所有测试的化合物中，6-羟基-2-（2-（三氟甲氧基）苄基）-2,3-二氢-1H- Inden-1-On（化合物44）显示ROS生产的最强抑制活性。进一步研究作用方式显示，化合物44通过NADPH氧化酶的调节效果抑制了LPS刺激的ROS产生。这项工作的发现可用于设计基于2-苄基 - 吲哚酮的铅化合物作为新型抗炎剂。（c）2017年Elsevier Masson SAS。版权所有。

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来源
《European Journal of Medicinal Chemistry: Chimie Therapeutique》 |2017年第2017期|共18页
作者
Shrestha Aarajana; Oh Hye Jin; Kim Mi Jin; Pun Nirmala Tilija; Magar Til Bahadur Thapa; Bist Ganesh; Choi Hongseok; Park Pil-Hoon; Lee Eung-Seok;
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作者单位

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

Yeungnam Univ Coll Pharm Gyongsan 712749 South Korea;

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原文格式 PDF
正文语种 eng
中图分类药学;
关键词
Halogen containing 2-benzylidene-1-indanone; Anti-inflammatory agents; Inhibition of ROS production; RAW 264.7 macrophages; Structure-activity relationship;

机译：含有2-苄基-1-indanone的卤素;抗炎剂;抑制ROS生产;生成264.7巨噬细胞;结构 - 活动关系;

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1. Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages [J] . Shrestha Aarajana, Oh Hye Jin, Kim Mi Jin, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2017,第期

机译：含有2-苄基-1-吲哚酮衍生物的卤素的设计，合成和结构 - 活性研究抑制LPS刺激的ROS型ROS生产中的RAP 264.7巨噬细胞
2. Design and Synthesis of Fluorinated and/or Hydroxylated 2-Arylidene- 1-indanone Derivatives as an Inhibitor of LPS-stimulated ROS Production in EAW 264.7 Macrophages with Structure-Activity Relationship Study [J] . Pramila Katila, Aastha Shrestha, Aarajana Shrestha Bulletin of the Korean Chemical Society . 2018,第12期

机译：氟化和/或羟基化2-亚亚亚亚亚亚亚亚亚亚亚亚亚亚亚亚芳基1-吲哚酮衍生物的设计和合成LPS刺激的ROS生产中的抑制作用，具有结构 - 活性关系研究的巨噬细胞
3. Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study [J] . Bist Ganesh, Pun Nirmala Tilija, Magar Til Bahadur Thapa, Bioorganic and Medicinal Chemistry Letters . 2017,第5期

机译：用结构 - 活性关系研究抑制氟化和羟基硫氨酸的LPS刺激的ROS产生的氟化和羟基的氯丙酮
4. Comparison of Inhibitory Effects of Nine Flavonoids on Prostaglandin E2 Production and COX-2 Expression in LPS-Stimulated RAW264.7 Macrophages [C] . Xu Yirong, Wang Changlu, Wu Longyan, Biomedical Engineering and Biotechnology (iCBEB), 2012 International Conference on . 2012

机译：比较九种黄酮类化合物对LPS刺激的RAW264.7巨噬细胞中前列腺素E2产生和COX-2表达的抑制作用。
5. Isolated Polyphenols and Farnesol, Stable in Culture Medium, Function Synergistically in a Hormesial Manner to Modulate LPS-stimulated Raw 264.7 Macrophage Polarization toward the M0 or M2 State under Multiple Paradigms [D] . Murphy, Cameron C. 2018

机译：分离的多酚和法尼醇，在培养基中稳定，以激素方式协同作用，在多种范式下向L0刺激的原始264.7巨噬细胞极化向M0或M2状态。
6. Pro-oxidant activity of indicaxanthin from Opuntia ficus indica modulates arachidonate metabolism and prostaglandin synthesis through lipid peroxide production in LPS-stimulated RAW 264.7 macrophages [O] . M. Allegra, F. D’Acquisto, L. Tesoriere, 2014

机译：来自印度仙人掌的印度洋黄嘌呤的促氧化活性通过脂过氧化物的产生来调节脂多糖刺激的RAW 264.7巨噬细胞中花生四烯酸的代谢和前列腺素的合成。
7. Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study [O] . Tara Man Kadayat, Mi Jin Kim, Tae-Gyu Nam, 2014

机译：Inieny / Furanyl-羟基苯丙烯酮作为LPS诱导的ROS抑制剂，无需生产264.7巨噬细胞，其结构 - 活动关系研究

Design, synthesis, and structure-activity relationship study of halogen containing 2-benzylidene-1-indanone derivatives for inhibition of LPS-stimulated ROS production in RAW 264.7 macrophages

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