3'-bromo-3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl | 1375102-84-3

• 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: 3'-bromo-3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl
• 英文别名: 3',5-diallyl-3-bromo-4'-methoxy-[1,1'-biphenyl]-2-ol；2-Bromo-6-(4-methoxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
• CAS: 1375102-84-3
• 化学式: C₁₉H₁₉BrO₂
• 分子量: 359.263
• InChiKey: YTTQAFLXAUBCGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4'-甲氧基-3',5-二-2-丙烯基-(1,1'-联苯)-2-醇 在 异丙基氯化镁 、 1,3-二溴-5,5-二甲基海因 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.67h， 以66%的产率得到3'-bromo-3,5'-diallyl-2'-hydroxy-4-methoxy-1,1'-biphenyl
  参考文献：
  名称：

  Design and synthesis of 4-O-methylhonokiol analogs as inhibitors of cyclooxygenase-2 (COX-2) and PGF1 production

  摘要：

  A series of novel 4-O-methylhonokiol analogs were synthesized in light of revealing structure-activity relationship for inhibitory effect of COX-2 enzyme. The key strategy of the molecular design was oriented towards modification of the potential metabolic soft spots (e. g., phenol and olefin) or by altering the polar surface area via incorporating heterocycles such as isoxazole and triazole. Most of all exhibited the inhibitory effects on COX-2 and PGF(1) production but not macrophage NO production. Especially, aryl carbamates 10 and 11 exhibited more potent inhibitory activity against COX-2 and PGF(1) production. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.028

文献信息

• In vitro growth inhibition of human cancer cells by novel honokiol analogs
  作者：Jyh Ming Lin、A.S. Prakasha Gowda、Arun K. Sharma、Shantu Amin

  DOI：10.1016/j.bmc.2012.03.062

  日期：2012.5

  Honokiol possesses many pharmacological activities including anti-cancer properties. Here in, we designed and synthesized honokiol analogs that block major honokiol metabolic pathway which may enhance their effectiveness. We studied their cytotoxicity in human cancer cells and evaluated possible mechanism of cell cycle arrest. Two analogs, namely 2 and 4, showed much higher growth inhibitory activity in A549 human lung cancer cells and significant increase of cell population in the G0-G1 phase. Further elucidation of the inhibition mechanism on cell cycle showed that analogs 2 and 4 inhibit both CDK1 and cyclin B1 protein levels in A549 cells. (C) 2012 Elsevier Ltd. All rights reserved.
• Design and synthesis of 4-O-methylhonokiol analogs as inhibitors of cyclooxygenase-2 (COX-2) and PGF1 production
  作者：Bit Lee、Jae-Hwan Kwak、Shin-Won Huang、Jae-Yong Jang、Sanglae Lim、Young-Shin Kwak、Kiho Lee、Hyung Sook Kim、Sang-Bae Han、Jin-Tae Hong、Heesoon Lee、Sukgil Song、Seung-Yong Seo、Jae-Kyung Jung

  DOI：10.1016/j.bmc.2012.03.028

  日期：2012.5

  A series of novel 4-O-methylhonokiol analogs were synthesized in light of revealing structure-activity relationship for inhibitory effect of COX-2 enzyme. The key strategy of the molecular design was oriented towards modification of the potential metabolic soft spots (e. g., phenol and olefin) or by altering the polar surface area via incorporating heterocycles such as isoxazole and triazole. Most of all exhibited the inhibitory effects on COX-2 and PGF(1) production but not macrophage NO production. Especially, aryl carbamates 10 and 11 exhibited more potent inhibitory activity against COX-2 and PGF(1) production. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.