Methyl 2-[3-(cyanomethyl)-6-phenylmethoxyindol-1-yl]acetate | 1447648-54-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2-[3-(cyanomethyl)-6-phenylmethoxyindol-1-yl]acetate
• 英文别名: methyl 2-[3-(cyanomethyl)-6-phenylmethoxyindol-1-yl]acetate
• CAS: 1447648-54-5
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: BDPPJNQZVWRJTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2-[3-(cyanomethyl)-6-phenylmethoxyindol-1-yl]acetate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以71%的产率得到Methyl 2-[3-(cyanomethyl)-6-hydroxyindol-1-yl]acetate
  参考文献：
  名称：

  Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

  摘要：

  Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE(2) productions and was less cytotoxic than arvelexin on macrophage cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.114
• 作为产物：
  描述：

  6-苄氧基吲哚-3-甲醛 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 formamide 为溶剂， 生成 Methyl 2-[3-(cyanomethyl)-6-phenylmethoxyindol-1-yl]acetate
  参考文献：
  名称：

  Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

  摘要：

  Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE(2) productions and was less cytotoxic than arvelexin on macrophage cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.114

文献信息

• Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells
  作者：Tae Hoon Kwon、Ik Hwan Yoon、Ji-Sun Shin、Young Hun Lee、Bong Jin Kwon、Kyung-Tae Lee、Yong Sup Lee

  DOI：10.1016/j.bmcl.2013.02.114

  日期：2013.5

  Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE(2) productions and was less cytotoxic than arvelexin on macrophage cells. (C) 2013 Elsevier Ltd. All rights reserved.