3,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(E)-ylidene)-4-piperidone hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(E)-ylidene)-4-piperidone hydrochloride
• 英文别名: (3E,5E)-3,5-bis[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]piperidin-4-one;hydrochloride
• 化学式: C₂₁H₁₉Br₂NO₅*ClH
• 分子量: 561.654
• InChiKey: LCGJZUXJNWJATP-USYMAKMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 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：
  88
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-哌啶酮 、 5-溴香兰素 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 以75%的产率得到3,5-bis(3-bromo-4-hydroxy-5-methoxybenz-(E)-ylidene)-4-piperidone hydrochloride
  参考文献：
  名称：

  α-Glucosidase inhibition of natural curcuminoids and curcumin analogs

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2005.10.012

文献信息

• 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.