manthine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: manthine
• 英文别名: Manthin；(1S,13S,15S,16S)-15,16-dimethoxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.013,18]nonadeca-2,4(8),9,17-tetraene
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: RCRQUNONAXMKLF-VGWMRTNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢化钾 、 对甲苯磺酸甲酯 、 苯 作用下， 生成 manthine
  参考文献：
  名称：

  Structures of Montanine, Coccinine, and Manthine¹

  摘要：

  DOI：

  10.1021/jo01082a019

文献信息

• An Expedient Route to Montanine-Type Amaryllidaceae Alkaloids: Total Syntheses of (−)-Brunsvigine and (−)-Manthine
  作者：An-Wei Hong、Tsung-Hui Cheng、Vellingiri Raghukumar、Chin-Kang Sha

  DOI：10.1021/jo801089y

  日期：2008.10.3

  Grignard addition of 8 to 9 and detosylation afforded amine derivative 19. Pictet-Spengler cyclization of 19 with Eschenmoser's salt and subsequent hydrolysis gave enantiomerically pure (-)-brunsvigine (1). For the total synthesis of (-)-manthine (2), the key intermediate 7 was hydrolyzed to diol 21. Conversion of 21 into 22 followed by regioselective cleavage with DIBAL furnished alcohol 25. Alcohol 25 was

  （-）-brunsvigine（1）和（-）-manthine（2）的第一个总合成分别以10和18个步骤完成。通过五个步骤将（-）-亚硫酸转化为烯酮12。对烯酮12进行碘化，然后进行立体选择性还原，得到α-碘代烯丙基醇16。将醇16转化为Weinreb酰胺11，然后进行阴离子环化，得到双环烯酮10。对烯酮10进行立体选择性还原并随后进行保护，得到新戊酸酯9。格氏加成8至9和脱甲苯磺酰化得到胺衍生物19。用埃森莫瑟盐将Pictet-Spengler 19进行Pictet-Spengler环化，随后水解得到对映体纯的（-）-brunsvigine（1）。为了全合成（-）-甘氨酸（2），将关键中间体7水解为二醇21。
• Antiproliferative activity and apoptosis-inducing mechanism of Amaryllidaceae alkaloid montanine on A549 and MOLT-4 human cancer cells
  作者：Darja Koutova、Negar Maafi、Darina Muthna、Karel Kralovec、Jana Kroustkova、Filip Pidany、Abdul Aziz Timbilla、Eva Cermakova、Lucie Cahlikova、Martina Rezacova、Radim Havelek

  DOI：10.1016/j.biopha.2023.115295

  日期：2023.10

  10 μM to explore their cytotoxic activities against a panel of eight cancer cell lines and one non-cancer cell line. Among montanine and its analogues, montanine and its derivatives 12 and 14 showed the highest cytostatic activity in the initial single-dose screening. However, the native montanine exhibited the greatest antiproliferative activity against cancer cells, with a lower mean IC50 value of

  石蒜科中发现的异喹啉生物碱因其可用于开发新药的特性而引起人们的关注。山宁对癌细胞发挥抑制作用的可能分子机制尚未有记录。在本研究中，以 10 μM 的单次测试剂量筛选了山楂碱、曼山碱和一系列源自母体生物碱山楂碱的 15 种半合成山楂碱类似物，以探索它们对一组八种癌细胞系和一种非癌症细胞系的细胞毒性活性。细胞系。在montanine及其类似物中，montanine及其衍生物12和14在最初的单剂量筛选中显示出最高的细胞抑制活性。然而，天然山煤碱对癌细胞表现出最大的抗增殖活性，平均IC 50值较低，为1.39 µM，而12的平均IC 50值为2.08 µM ， 14的平均IC 50 值为3.57 µM 。Montanine对 Jurkat 和 A549 细胞系表现出最有效的抗增殖活性，IC 50值分别为 1.04 µM 和 1.09 µM。我们还评估了山地宁的细胞毒性和细胞死亡机制。我们的结果表明，山楂碱通过
• 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.