吗啉,4-[(2R)-3-[4-(1,1-二甲基丙基)苯基]-2-甲基丙基]-2,6-二甲基-,(2R,6S)- | 466-73-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 中文名称: 吗啉,4-[(2R)-3-[4-(1,1-二甲基丙基)苯基]-2-甲基丙基]-2,6-二甲基-,(2R,6S)-
• 英文名称: haemanthamidine
• 英文别名: haemanthidine；pancratine；ent-(11S)-3α-methoxy-crin-1-ene-6α,11-diol；Pancratin, Haemanthidin；Haemanthidin；Pancratin；Hemanthidine；(1S,11S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene-11,18-diol
• CAS: 466-73-9
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: ZSTPNQLNQBRLQF-UAQFGPKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吗啉,4-[(2R)-3-[4-(1,1-二甲基丙基)苯基]-2-甲基丙基]-2,6-二甲基-,(2R,6S)- 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 6-O-methylpretazettine
  参考文献：
  名称：

  Amaryllidaceae interconversions. Partial syntheses of [2]benzopyrano[3,4-c]indoles

  摘要：

  DOI：

  10.1021/ja01029a030

文献信息

• Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells
  作者：Karthik Govindaraju、Aude Ingels、Md Nabiul Hasan、Dandan Sun、Veronique Mathieu、Marco Masi、Antonio Evidente、Alexander Kornienko

  DOI：10.1016/j.bmcl.2018.01.041

  日期：2018.2

  In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit proliferation of cancer cells resistant to apoptosis at micromolar concentrations. Selected compounds were also active against patient-derived glioblastoma cells expressing stem-cell markers. This is the first report describing the preparation of synthetic analogues of the montanine-type alkaloids with antiproliferative activity. The compounds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with poor prognoses. (C) 2018 Elsevier Ltd. All rights reserved.
• 6-Hydroxycrinamine and Haemanthidine
  作者：R. W. King、C. F. Murphy、W. C. Wildman

  DOI：10.1021/ja00949a039

  日期：1965.11
• Amaryllidaceae interconversions. Partial syntheses of [2]benzopyrano[3,4-c]indoles
  作者：William C. Wildman、David T. Bailey

  DOI：10.1021/ja01029a030

  日期：1969.1