methyl 1-(2-methyl-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

• 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 1-(2-methyl-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl 1-isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate；methyl 1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: LFBDUYMSBJXRJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]methyl]cyclohexane-1-carboxylic acid 、 methyl 1-(2-methyl-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 在 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 以52%的产率得到methyl 2-(trans-4-((tert-butoxycarbonyl(methyl)amino)methyl)cyclohexanecarbonyl)-1-isobutyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  [EN] AGENTS FOR DIFFERENTIATING STEM CELLS AND TREATING CANCER
  [FR] AGENTS POUR DIFFÉRENCIER DES CELLULES SOUCHES ET TRAITER UN CANCER

  摘要：

  本申请公开了一种用于识别治疗或预防癌症或转移性癌症的药剂的方法，包括以下步骤：将干细胞与潜在药剂接触，并识别诱导分化的药剂，或抑制干细胞多能性或干细胞生长的药剂，其中这种药剂被确定为抗癌药剂。

  公开号：

  WO2018183654A1
• 作为产物：
  描述：

  L-色氨酸 在 氯化亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl 1-(2-methyl-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.12.028

文献信息

• AGENTS FOR DIFFERENTIATING STEM CELLS AND TREATING CANCER
  申请人：Minerva Biotechnologies Corporation

  公开号：US20210087143A1

  公开（公告）日：2021-03-25

  The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.
• AGENTS FOR TREATING CANCER AND METHODS FOR IDENTIFYING SAID AGENTS
  申请人：MINERVA BIOTECHNOLOGIES CORPORATION

  公开号：US20210299109A1

  公开（公告）日：2021-09-30

  The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.
• [EN] AGENTS FOR DIFFERENTIATING STEM CELLS AND TREATING CANCER<br/>[FR] AGENTS POUR DIFFÉRENCIER DES CELLULES SOUCHES ET TRAITER UN CANCER
  申请人：MINERVA BIOTECHNOLOGIES CORP

  公开号：WO2018183654A1

  公开（公告）日：2018-10-04

  The present application discloses a method for identifying an agent for the treatment or prevention of cancer or metastatic cancer comprising the steps of contacting stem cell with a potential agent, and identifying an agent that induces differentiation, or inhibits stem cell pluripotency or growth of the stem cell, wherein such agent is determined to be an anti-cancer agent.

  本申请公开了一种用于识别治疗或预防癌症或转移性癌症的药剂的方法，包括以下步骤：将干细胞与潜在药剂接触，并识别诱导分化的药剂，或抑制干细胞多能性或干细胞生长的药剂，其中这种药剂被确定为抗癌药剂。
• 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.