2,5-bis(3,5-di-tert-butyl-4-hydroxybenz-(E)-ylidene)cyclopentanone

• 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(3,5-di-tert-butyl-4-hydroxybenz-(E)-ylidene)cyclopentanone
• 英文别名: 2,5-bis-(3,5-di-tert-butyl-4-hydroxybenzylidene)cyclopentanone；2,5-Bis(3,5-di-tert-butyl-4-hydroxybenzylidene)cyclopentanone；(2E,5E)-2,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]cyclopentan-1-one
• 化学式: C₃₅H₄₈O₃
• 分子量: 516.764
• InChiKey: AWUSJMKLSWCCKF-DFEHQXHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环戊酮 、 3,5-二叔丁基-4-羟基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以82%的产率得到2,5-bis(3,5-di-tert-butyl-4-hydroxybenz-(E)-ylidene)cyclopentanone
  参考文献：
  名称：

  姜黄素类似物作为强效醛糖还原酶抑制剂

  摘要：

  在本研究中，从姜黄中分离的姜黄素被证明对牛晶状体醛糖还原酶具有抑制活性。为了找到更有效的醛糖还原酶抑制剂，合成了姜黄素类似物并评估了它们抑制牛晶状体醛糖还原酶的能力。结果表明，具有四羟基基团的化合物、2,6-双(3,4-二羟基亚苄基)环己酮(A2)、2,5-双(3,4-二羟基亚苄基)环戊酮(B2)、1,5-双( 3,4-二羟基苯基)-1,4-戊二烯-3-一(C2)和3,5-双(3,4-二羟基苯亚甲基)-4-哌啶酮(D2)对醛糖还原酶具有显着的抑制作用，IC50分别为 2.9 μM、2.6 μM、3.4 μM 和 4.9 μM。

  DOI：

  10.1002/ardp.200500205

文献信息

• Curcumin Analogs as Potent Aldose Reductase Inhibitors
  作者：Zhi-Yun Du、Ya-Dan Bao、Zhong Liu、Wei Qiao、Lin Ma、Zhi-Shu Huang、Lian-Quan Gu、Albert S. C. Chan

  DOI：10.1002/ardp.200500205

  日期：2006.3

  study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6‐bis(3,4‐dihydroxybenzylidene)cyclohexanone

  在本研究中，从姜黄中分离的姜黄素被证明对牛晶状体醛糖还原酶具有抑制活性。为了找到更有效的醛糖还原酶抑制剂，合成了姜黄素类似物并评估了它们抑制牛晶状体醛糖还原酶的能力。结果表明，具有四羟基基团的化合物、2,6-双(3,4-二羟基亚苄基)环己酮(A2)、2,5-双(3,4-二羟基亚苄基)环戊酮(B2)、1,5-双( 3,4-二羟基苯基)-1,4-戊二烯-3-一(C2)和3,5-双(3,4-二羟基苯亚甲基)-4-哌啶酮(D2)对醛糖还原酶具有显着的抑制作用，IC50分别为 2.9 μM、2.6 μM、3.4 μM 和 4.9 μM。
• α-Glucosidase inhibition of natural curcuminoids and curcumin analogs
  作者：Zhi-yun Du、Rong-rong Liu、Wei-yan Shao、Xue-pu Mao、Lin Ma、Lian-quan Gu、Zhi-shu Huang、Albert S.C. Chan

  DOI：10.1016/j.ejmech.2005.10.012

  日期：2006.2

  Natural curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) isolated from Curcuma longa (turmeric), and synthetic curcumin analogs (A(1-7), B1-7, C1-6 and D1-7) were evaluated in vitro for the a-glucosidase inhibitory activity via UV and circular dichroism (CD) spectroscopy. The results indicated that natural curcuminoid compound 3 showed a remarkable inhibitory effect with IC50 of 23.0 mu M, and the synthetic compounds A(2), B-2, C-2 and D-2 showed potent inhibitory effects with IC50 of 2.8, 2.6, 1.6 and 8.2 mu M, respectively. Kinetic study exhibited that the mechanism of alpha-glucosidase inhibition of both 3 and C-2 was non-competitive. The structure activity relationship revealed that the ortho dihydroxyl groups could form a more tight interaction with a-glucosidase to exert more potential inhibitory activities. (c) 2006 Elsevier SAS. All fights reserved.
• 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship
  作者：S.S. Sardjiman、M.S. Reksohadiprodjo、L Hakim、H van der Goot、H Timmerman

  DOI：10.1016/s0223-5234(97)83288-6

  日期：1997.7

  A series of 1,5-diphenyl-1,4-pentadiene-3-ones and cyclic analogues with OH-groups in the pam position of the phenyl rings and various meta substituents were prepared and their antioxidant activity compared with that of curcumin. Most of them exhibited potent antioxidative activity, especially when all the meta positions were substituted by methoxy groups.
• The synthesis, spectroscopic characterization and structure of three bis(arylmethylidene)cyclopentanones
  作者：Yi-Feng Sun、Zhu-Yuan Wang、Xue Zhao、Ze-Bao Zheng、Ji-Kun Li、Ren-Tao Wu、Yi-Ping Cui

  DOI：10.1016/j.dyepig.2009.12.010

  日期：2010.6

  Three bis(arylmethylidene)cyclopentanone dyes were synthesized and their structures and properties elucidated using single-crystal X-ray diffraction, mass spectrometry, 1H nuclear magnetic resonance, IR and UV–Vis spectroscopy. X-ray analyses revealed that two were monoclinic, with space group P21/c, while the third dye was triclinic, with space group P1¯. All three molecules adopted an E-configuration

  合成了三种双（芳基亚甲基）环戊酮染料，并使用单晶X射线衍射，质谱，1 H核磁共振，IR和UV-Vis光谱对它们的结构和性质进行了阐明。X射线分析表明，两种是单斜晶系，其空间群为P 2 1 / c，而第三种染料是三斜晶系，其空间群为P1个¯。这三个分子都围绕中心烯烃键采用E-构型，呈现蝴蝶形的几何形状。利用密度泛函理论的分子结构优化表明，优化后的几何参数与实验值基本吻合。另外，推导了最高的占据分子轨道水平和最低的未占据分子轨道水平。