1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 1245793-13-8

• 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: 1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 1-(oxan-4-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 1245793-13-8
• 化学式: C₁₇H₂₂N₂O
• 分子量: 270.374
• InChiKey: OVJDVWATPBKCLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-四氢吡喃基乙醛 、 色胺盐酸盐 在 顺丁烯二酸 作用下， 以 水 为溶剂， 生成 1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Biocatalytic asymmetric formation of tetrahydro-β-carbolines

  摘要：

  Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetlet.2010.06.075

文献信息

• Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives
  作者：Nicole Sudžuković、Johann Schinnerl、Lothar Brecker

  DOI：10.1016/j.bmc.2015.12.028

  日期：2016.2

  Synthesis of 13 different tetrahydro-beta-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and L-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of a-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-beta-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products. (c) 2015 Elsevier Ltd. All rights reserved.