2,5-bis(m-bromobenzylidene)cyclopentanone | 1018785-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis(m-bromobenzylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(3-bromobenzylidene)cyclopentanone；2,5-Bis(3-bromobenzylidene)cyclopentanone；(2E,5E)-2,5-bis[(3-bromophenyl)methylidene]cyclopentan-1-one
• CAS: 1018785-62-0
• 化学式: C₁₉H₁₄Br₂O
• 分子量: 418.128
• InChiKey: MQKBSTJEWWWOFG-KAVGSWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-bis(m-bromobenzylidene)cyclopentanone 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-(3-Bromo-phenyl)-7-[1-(3-bromo-phenyl)-meth-(E)-ylidene]-2-methylsulfanyl-6,7-dihydro-5H-cyclopentapyrimidine
  参考文献：
  名称：

  核酸成分及其类似物：双环硫嘧啶核苷的新合成

  摘要：

  摘要描述了一种以1H-环戊嘧啶-2（3H）-硫酮和α-溴葡萄糖或α-溴半乳糖四乙酸酯为起始成分的稠合双环硫代嘧啶糖苷的合成方法。

  DOI：

  10.1080/15257770008035020
• 作为产物：
  描述：

  间溴苯甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以91%的产率得到2,5-bis(m-bromobenzylidene)cyclopentanone
  参考文献：
  名称：

  Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin

  摘要：

  本文描述了三种单羰基姜黄素类似物的合成。对七种革兰氏阳性和革兰氏阴性细菌进行了体外抗菌活性测试，并讨论了取代基对芳环和连接张力的空间结构的影响。观察到，与姜黄素相比，部分衍生物显示出显著的活性，并且大多数衍生物对氨苄西林抵抗的阴沟肠杆菌表现出活性。化合物A12、B09、B13、B14和C09显示出显著的体外抗菌活性。结果显示，杂环或长链取代基可能增强姜黄素类似物的活性。

  DOI：

  10.1248/cpb.56.162

文献信息

• Ananthakrishna Nadar; Renuga, Journal of the Indian Chemical Society, 2006, vol. 83, # 12, p. 1219 - 1222
  作者：Ananthakrishna Nadar、Renuga

  DOI：——

  日期：——
• Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin
  作者：Guang Liang、Xiaokun Li、Li Chen、Shulin Yang、Xudong Wu、Elaine Studer、Emily Gurley、Phillip B. Hylemon、Faqing Ye、Yueru Li、Huiping Zhou

  DOI：10.1016/j.bmcl.2007.12.068

  日期：2008.2

  Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The beta-diketone moiety renders curcumin to be rapidly metabolized by aldo -keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide ( LPS)-induced TNF-alpha and IL-6 synthesis in macrophages. (C) 2007 Elsevier Ltd. All rights reserved.
• SmI₃Catalyzed Condensation of Aliphatic Cycloketones and Aldehydes in Ionic Liquid
  作者：Xingliang Zheng、Yongmin Zhang

  DOI：10.1081/scc-120015572

  日期：2003.3

  SmI3 catalyzed condensation of aliphatic cycloketones and aldehydes was studied in ionic liquid. 2,5-Dibenzyldiene cyclopentanones and 2,6-dibenzyldienecyclohexanones were prepared in high yields under convenient conditions.
• Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors
  作者：Han Lin、Guo-Xin Hu、Jingjing Guo、Yufei Ge、Guang Liang、Qing-Quan Lian、Yanhui Chu、Xiaohuan Yuan、Ping Huang、Ren-Shan Ge

  DOI：10.1016/j.bmcl.2013.05.080

  日期：2013.8

  A series of structurally novel mono-carbonyl curcumin analogues have been synthesized and biologically evaluated to test their inhibitory potencies and the structure-activity relationship (SAR) on human and rat 11 beta-hydroxysteroid dehydrogenase isoform (11 beta-HSD1) activities. 11 beta-HSD1 selective inhibitors have been discovered and compound A10 is discovered as a very potent with an IC50 value of 97 nM without inhibiting 11 beta-HSD2. (C) 2013 Elsevier Ltd. All rights reserved.