1-benzyl-2,3,4,9-tetrahydro-1H-β-carboline; hydrochloride | 50315-78-1

• 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-benzyl-2,3,4,9-tetrahydro-1H-β-carboline; hydrochloride
• 英文别名: 1-Benzyl-2,3,4,9-tetrahydro-1H-β-carbolin; Hydrochlorid；1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;hydrochloride
• CAS: 50315-78-1
• 化学式: C₁₈H₁₈N₂*ClH
• 分子量: 298.815
• InChiKey: QMKQCMSYVQABHD-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C(Solv: acetic acid (64-19-7))

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Boc-5-氨基戊酸 、 1-benzyl-2,3,4,9-tetrahydro-1H-β-carboline; hydrochloride 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 以63%的产率得到tert-butyl N-[5-(1-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)-5-oxopentyl]carbamate
  参考文献：
  名称：

  METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS

  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：

  US20180263964A1
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 sodium acetate 、 乙酸酐 作用下， 以 水 为溶剂， 反应 1.0h， 生成 1-benzyl-2,3,4,9-tetrahydro-1H-β-carboline; hydrochloride
  参考文献：
  名称：

  METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS

  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：

  US20180263964A1

文献信息

• Monoamine Oxidase (MAO-N) Catalyzed Deracemization of Tetrahydro-β-carbolines: Substrate Dependent Switch in Enantioselectivity
  作者：Diego Ghislieri、Deborah Houghton、Anthony P. Green、Simon C. Willies、Nicholas J. Turner

  DOI：10.1021/cs400724g

  日期：2013.12.6

  The tetrahydro-beta-carboline (THBC) ring system is an important structural motif found in a large number of bioactive alkaloid natural products. Herein we report a broadly applicable method for the synthesis of enantiomerically pure beta-carbolines via a deracemization procedure employing the D9 and D11 variants of monoamine oxidase from Aspergillus niger (MAO-N) in combination with a nonselective chemical reducing agent. Biotransformations were performed on a preparative scale, leading to the synthesis of optically enriched products in excellent enantiomeric excess (e.e.; up to 99%) and isolated yield (up to 93%). Interestingly, a switch in enantioselectivity associated with the MAO-N variants is observed as the nature of the C-1 substituent of the THBC is varied. Molecular modeling provided an explanation for this observation and highlighted key active site residues which were modified, resulting in an increase in (R)-selectivity associated with the enzyme. These results provide insight into the factors which influence the selectivity of the MAO-N variants, and may offer a platform for future directed evolution projects aimed toward the challenge of engineering (R)-selective amine oxidase biocatalysts.
• Microwave‐Assisted One‐Pot Preparation of Tetrahydro‐β‐carboline Hydrochlorides under Solvent‐Free Conditions
  作者：Fei Liu、Qi‐Dong You

  DOI：10.1080/00397910701572555

  日期：2007.11

  An efficient and environmentally friendly synthesis of tetrahydro-beta-carboline hydrochlorides via Pictet-Spengler reaction was described. Tryptamine hydrochlorides were used as the reactant and no additional acid catalyst was needed. This reaction was completed within 2.5-9 min in good yield.
• US5169852A
  申请人：——

  公开号：US5169852A

  公开（公告）日：1992-12-08
• [EN] METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS<br/>[FR] PROCÉDÉ DE SÉLECTION D'AGENTS POUR DIFFÉRENCIER DES CELLULES SOUCHES
  申请人：MINERVA BIOTECHNOLOGIES CORP

  公开号：WO2017053886A2

  公开（公告）日：2017-03-30

  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.
• METHOD OF SCREENING FOR AGENTS FOR DIFFERENTIATING STEM CELLS
  申请人：MINERVA BIOTECHNOLOGIES CORPORATION

  公开号：US20180263964A1

  公开（公告）日：2018-09-20

  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。