3,4-bis(allyloxy)phenylacetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-bis(allyloxy)phenylacetic acid
• 英文别名: 3,4-bis(2-propenyloxy)benzeneacetic acid；2-(3,4-Bis(allyloxy)phenyl)acetic acid；2-[3,4-bis(prop-2-enoxy)phenyl]acetic acid
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: SRRWXUCWLNMZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3,4-二羟基苯乙酸	3,4-dihydroxyphenylacetate	102-32-9	C8H8O4	168.149

反应信息

• 作为反应物：
  描述：

  3,4-bis(allyloxy)phenylacetic acid 在 4-二甲氨基吡啶 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3,4-bis(allyloxy)phenylethyl 4-O-((trans)-3,4-bis(allyloxy)phenylacetyl)-6-O-alloc-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents

  摘要：

  Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PCl2 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PCl2 cells in a dose-dependent manner. The antiapoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.038
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 、 3-溴丙烯 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以92%的产率得到3,4-bis(allyloxy)phenylacetic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

  摘要：

  合成了一系列 3-苯乙烯基色酮衍生物（4-20），并分析了其抑制α-葡萄糖苷酶和抗氧化活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 15 和 20 同时显示出强大的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（15：EC50=17 µM；20：EC50=23 µM）和α-葡萄糖苷酶抑制活性（15：IC50=16 µM；20：IC50=10 µM）。我们的数据表明，3-strylchromone 衍生物是新型的 α-葡萄糖苷酶抑制剂，具有抵消饮食引起的糖尿病高血糖的潜力。

  DOI：

  10.1248/cpb.c14-00351

文献信息

• 苯乙醇苷类似物及其合成方法和应用
  申请人：北京大学

  公开号：CN105985389B

  公开（公告）日：2019-03-19

  本发明公开了苯乙醇苷类似物及其合成方法和应用。本发明利用生物电子等排体等药物设计原理改造类叶升麻苷获得一系列具有神经保护活性的苯乙醇苷衍生物、唾液酸甲苷甲酯衍生物以及9‑脱羧迷迭香酸类化合物。本发明进一步提供了苯乙醇苷类似物的合成方法。神经药理实验研究发现，本发明苯乙醇苷类似物通过抗凋亡、抗氧化损伤等途径，增加细胞存活率、降低细胞凋亡率、抑制细胞内活性氧的产生，明显减轻细胞的损伤，发挥神经保护作用。本发明所提供的苯乙醇苷类似物在预防或治疗包括神经退行性疾病、脑缺血等在内的神经性疾病中具有重要的应用潜力。
• Synthesis and Biological Evaluation of 3-Styrylchromone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors
  作者：Koichi Takao、Ryo Ishikawa、Yoshiaki Sugita

  DOI：10.1248/cpb.c14-00351

  日期：——

  A series of 3-styrylchromone derivatives (4–20) were synthesized and the structure–activity relationships for α-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC50=17 µM; 20: EC50=23 µM) and α-glucosidase inhibitory activity (15: IC50=16 µM; 20: IC50=10 µM). Our data suggest that 3-styrylchromone derivatives are novel α-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.

  合成了一系列 3-苯乙烯基色酮衍生物（4-20），并分析了其抑制α-葡萄糖苷酶和抗氧化活性的结构-活性关系。在合成的化合物中，含有儿茶酚分子的化合物 15 和 20 同时显示出强大的 1,1-二苯基-2-苦基肼（DPPH）自由基清除活性（15：EC50=17 µM；20：EC50=23 µM）和α-葡萄糖苷酶抑制活性（15：IC50=16 µM；20：IC50=10 µM）。我们的数据表明，3-strylchromone 衍生物是新型的 α-葡萄糖苷酶抑制剂，具有抵消饮食引起的糖尿病高血糖的潜力。
• Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents
  作者：Ying-Guo Liu、Xiaxi Li、De-Cai Xiong、Binhan Yu、Xiaoping Pu、Xin-Shan Ye

  DOI：10.1016/j.ejmech.2015.03.038

  日期：2015.5

  Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PCl2 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PCl2 cells in a dose-dependent manner. The antiapoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. (C) 2015 Elsevier Masson SAS. All rights reserved.