(2E,5E)-2,5-bis(2-hydroxy-3-methoxylbenzylidene)cyclopentanone | 1261266-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E,5E)-2,5-bis(2-hydroxy-3-methoxylbenzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[(2-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 1261266-22-1
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: NVWKLHFCBFSGDK-JOBJLJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-3-甲基苯甲醛 、 环戊酮 在 甲醇 、 sodium methylate 作用下， 以61.2%的产率得到(2E,5E)-2,5-bis(2-hydroxy-3-methoxylbenzylidene)cyclopentanone
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages

  摘要：

  Curcumin is a multifunctional natural product with regulatory effects on inflammation. However, a major limitation for the application of curcumin is its poor bioavailability. We previously demonstrated that the mono-carbonyl analogues of curcumin possessed improved pharmacokinetic profiles. In this study, 33 novel mono-carbonyl analogues of curcumin were synthesized and their inhibition against TNF-alpha and IL-6 release was evaluated in LPS-stimulated RAW 264.7 macrophages. Based on the screening data, quantitative structure activity relationship was conducted, indicating that electron-withdrawing groups in benzene ring are favourable to anti-inflammatory activities of B-class compounds. Furthermore, compounds AN1 and 1382 demonstrated anti-inflammatory abilities in a dose-dependent manner. These raise the possibility that these compounds might serve as potential agents for the treatment of inflammatory diseases. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.037

文献信息

• 5-Bis-(2,6-difluoro-benzylidene) Cyclopentanone Acts as a Selective 11β-Hydroxysteroid Dehydrogenase one Inhibitor to Treat Diet-Induced Nonalcoholic Fatty Liver Disease in Mice
  作者：Hongguo Guan、Yiyan Wang、Huitao Li、Qiqi Zhu、Xiaoheng Li、Guang Liang、Ren-Shan Ge

  DOI：10.3389/fphar.2021.594437

  日期：——

  Background: 11β-Hydroxysteroid dehydrogenase one is responsible for activating inert glucocorticoid cortisone into biologically active cortisol in humans and may be a novel target for the treatment of nonalcoholic fatty liver disease. Methods: A series of benzylidene cyclopentanone derivatives were synthesized, and the selective inhibitory effects on rat, mouse and human 11β-hydroxysteroid dehydrogenase one

  背景：11β-羟基类固醇脱氢酶是一种负责将惰性糖皮质激素可的松活化为人类生物活性皮质醇的药物，可能是治疗非酒精性脂肪肝的新靶标。方法：合成了一系列亚苄基环戊酮衍生物，并筛选了对大鼠，小鼠和人11β-羟类固醇脱氢酶一和二的选择性抑制作用。最有效的化合物[5-双-（2,6-二氟亚苄基）-环戊酮]（WZS08）用于治疗高脂饮食100天的小鼠的非酒精性脂肪肝疾病。结果：WZS08是大鼠，小鼠和人11β-羟基类固醇脱氢酶1的最有效抑制剂，最大抑制浓度分别为378.0、244.1和621.1 nM，一半，并且在100μM时它不影响11β-羟基类固醇脱氢酶2。当给小鼠喂WZS08（1、2和4 mg / kg）达100天时，WZS08显着降低了4 mg / kg的血清胰岛素水平和胰岛素指数。在1 mg / kg的低浓度下，WZS08显着降低了血清甘油三酸酯，胆固醇，低密度脂蛋白和肝脂肪的水平。在1 mg /
• Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages
  作者：Chengguang Zhao、Yuepiao Cai、Xuzhi He、Jianling Li、Li Zhang、Jianzhang Wu、Yunjie Zhao、Shulin Yang、Xiaokun Li、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2010.09.037

  日期：2010.12

  Curcumin is a multifunctional natural product with regulatory effects on inflammation. However, a major limitation for the application of curcumin is its poor bioavailability. We previously demonstrated that the mono-carbonyl analogues of curcumin possessed improved pharmacokinetic profiles. In this study, 33 novel mono-carbonyl analogues of curcumin were synthesized and their inhibition against TNF-alpha and IL-6 release was evaluated in LPS-stimulated RAW 264.7 macrophages. Based on the screening data, quantitative structure activity relationship was conducted, indicating that electron-withdrawing groups in benzene ring are favourable to anti-inflammatory activities of B-class compounds. Furthermore, compounds AN1 and 1382 demonstrated anti-inflammatory abilities in a dose-dependent manner. These raise the possibility that these compounds might serve as potential agents for the treatment of inflammatory diseases. (C) 2010 Elsevier Masson SAS. All rights reserved.