methyl (1R,3S,2'S,4'R,5'R)-1-(5'-phenylacetamino-4'-methyl-1',3'-dioxan-2'-yl)methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate | 1242686-19-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (1R,3S,2'S,4'R,5'R)-1-(5'-phenylacetamino-4'-methyl-1',3'-dioxan-2'-yl)methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
• 英文别名: methyl (1R,3S)-1-[[(2S,4R,5R)-4-methyl-5-[(2-phenylacetyl)amino]-1,3-dioxan-2-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1242686-19-6
• 化学式: C₂₇H₃₁N₃O₅
• 分子量: 477.56
• InChiKey: JXIIMJTUXNELED-IOOJMYGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1R,3S,2'S,4'R,5'R)-1-(5'-phenylacetamino-4'-methyl-1',3'-dioxan-2'-yl)methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 在 盐酸 、 penicillin acylase from Escherichia coli 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 methyl (1R,3S,2'S,4'R,5'R)-1-(5'-amino-4'-methyl-1',3'-dioxan-2'-yl)methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Novel Indole Derivatives Reveal Improved Therapeutic Agents for Treatment of Ischemia/Reperfusion (I/R) Injury

  摘要：

  To develop more potent therapeutic agents with therapeutic efficacy for ischemia/reperfusion (I/R) injury, we linked an antiinflammatory moiety (1,3-dioxane derivative) to the key pharmacophoric moiety of melatonin. We hypothesized that the resulting, new indole derivatives might induce a synergistic protection against oxidative damage associated with I/R injury. Our results indicate that one of these indole derivatives (7) manifests potent antiinflammatory antioxidant effects and exerts a protective effect against skeletal muscle injury and associated lung injury following limb I/R in rats.

  DOI：

  10.1021/jm100529e
• 作为产物：
  描述：

  (2S,4R,5R)-N-[2-(carbonylmethyl)-4-methyl-1,3-dioxan-5-yl]phenylacetamide 、 L-色氨酸甲酯 在 sodium sulfate 作用下， 以 氯仿 为溶剂， 反应 60.0h， 以55%的产率得到methyl (1R,3S,2'S,4'R,5'R)-1-(5'-phenylacetamino-4'-methyl-1',3'-dioxan-2'-yl)methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Novel Indole Derivatives Reveal Improved Therapeutic Agents for Treatment of Ischemia/Reperfusion (I/R) Injury

  摘要：

  To develop more potent therapeutic agents with therapeutic efficacy for ischemia/reperfusion (I/R) injury, we linked an antiinflammatory moiety (1,3-dioxane derivative) to the key pharmacophoric moiety of melatonin. We hypothesized that the resulting, new indole derivatives might induce a synergistic protection against oxidative damage associated with I/R injury. Our results indicate that one of these indole derivatives (7) manifests potent antiinflammatory antioxidant effects and exerts a protective effect against skeletal muscle injury and associated lung injury following limb I/R in rats.

  DOI：

  10.1021/jm100529e

文献信息

• Synthesis and Characterization of Novel Indole Derivatives Reveal Improved Therapeutic Agents for Treatment of Ischemia/Reperfusion (I/R) Injury
  作者：Wei Bi、Yue Bi、Ping Xue、Yanrong Zhang、Xiang Gao、Zhibo Wang、Meng Li、Michèle Baudy-Floc’h、Nathaniel Ngerebara、K. Michael Gibson、Lanrong Bi

  DOI：10.1021/jm100529e

  日期：2010.9.23

  To develop more potent therapeutic agents with therapeutic efficacy for ischemia/reperfusion (I/R) injury, we linked an antiinflammatory moiety (1,3-dioxane derivative) to the key pharmacophoric moiety of melatonin. We hypothesized that the resulting, new indole derivatives might induce a synergistic protection against oxidative damage associated with I/R injury. Our results indicate that one of these indole derivatives (7) manifests potent antiinflammatory antioxidant effects and exerts a protective effect against skeletal muscle injury and associated lung injury following limb I/R in rats.