3-methylbenzyl 3',4'-dihydroxybenzoate | 1070881-36-5

• 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-methylbenzyl 3',4'-dihydroxybenzoate
• 英文别名: (3-methylphenyl)methyl 3,4-dihydroxybenzoate
• CAS: 1070881-36-5
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: AJMOOANKAONKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原儿茶酸 、 3-甲基苄基氯 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以53%的产率得到3-methylbenzyl 3',4'-dihydroxybenzoate
  参考文献：
  名称：

  Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension

  摘要：

  Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.056

文献信息

• Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension
  作者：Osamu Ohno、Mao Ye、Tomoyuki Koyama、Kazunaga Yazawa、Emi Mura、Hiroshi Matsumoto、Takao Ichino、Kaoru Yamada、Kazuhiko Nakamura、Tomohiro Ohno、Kohji Yamaguchi、Junji Ishida、Akiyoshi Fukamizu、Daisuke Uemura

  DOI：10.1016/j.bmc.2008.03.056

  日期：2008.8

  Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension. (c) 2008 Elsevier Ltd. All rights reserved.