2,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(E)-ylidene)cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(E)-ylidene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]cyclopentan-1-one
• 化学式: C₂₁H₁₈Br₂O₅
• 分子量: 510.179
• InChiKey: GNAXSIHSKYFRTD-ACFHMISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 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：

  5-溴香兰素 、 环戊酮 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以45%的产率得到2,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(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.