(5S,9S)-13-bromo-4-methyl-4,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1(17),11(16),12,14-tetraen-9-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5S,9S)-13-bromo-4-methyl-4,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1(17),11(16),12,14-tetraen-9-ol
• 化学式: C₁₆H₁₉BrN₂O
• 分子量: 335.244
• InChiKey: SEKCREXSGCGPFK-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,9S)-13-bromo-4-methyl-4,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1(17),11(16),12,14-tetraen-9-ol 在 伯吉斯试剂 作用下， 以 苯 为溶剂， 反应 8.0h， 以84%的产率得到(5S)-13-bromo-4-methyl-4,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1(17),8,11(16),12,14-pentaene
  参考文献：
  名称：

  Antiproliferative activity of arborescidine alkaloids and derivatives

  摘要：

  Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.005
• 作为产物：
  描述：

  2-(1H-吲哚-3-基)-N-甲基-2-氧代乙酰胺 在 dimethyl sulfide borane 、 溴 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 5.42h， 生成 (5S,9S)-13-bromo-4-methyl-4,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1(17),11(16),12,14-tetraen-9-ol
  参考文献：
  名称：

  溴化海洋生物碱（±）-阿糖胞苷A，B和C的合成

  摘要：

  描述了从6-溴-（N-甲基）色胺的直接合成溴化海洋生物碱阿糖胞苷A（1），B（2）和C（3）的方法。的平衡，碱性和酸性条件下被发现之间存在反式-和顺式-异构体3和4。光谱数据表明，异构体4的结构与最近从海洋被膜植物假单胞菌假单胞菌中分离出的鉴定为阿糖胞苷D的化合物不符。

  DOI：

  10.1016/s0040-4020(98)00306-8

文献信息

• Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis
  作者：Vishal M. Sheth、Bor-Cherng Hong、Gene-Hsiang Lee

  DOI：10.1039/c7ob00473g

  日期：——

  A concise and enantioselective synthesis of the tetracyclic indoles, including the naturally occurring compounds (+)-arborescidine C and (+)-arborescidine B, was achieved by the key step of Pictet–Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst. The synthetic process was further demonstrated in a pot-economy strategy and was achieved in a one-pot operation.

  通过与雅各布森型硫脲有机催化剂进行Pictet-Spengler环化反应的关键步骤，可以实现包括自然存在的化合物（+）-碳硼烷C和（+）-碳硼烷B在内的四环吲哚的简明和对映选择性合成。合成工艺在锅经济策略中得到了进一步证明，并在一锅操作中得以实现。
• Antiproliferative activity of arborescidine alkaloids and derivatives
  作者：Leonardo S. Santos、Cristina Theoduloz、Ronaldo A. Pilli、Jaime Rodriguez

  DOI：10.1016/j.ejmech.2009.04.005

  日期：2009.9

  Current issues in cancer research involve searching for novel anticancer compounds that can be used to regulate the cell cycle and lead to more effective treatments of tumors. In this study, it was hypothesized that possessing a cyclic alkaloid similar to harmine, arborescidines can disrupt the proliferative state of cancer cells and block the activity of topoisomerases. The antiproliferative activity of arborescidines A-C and their derivatives was evaluated in vitro against four human tumor cell lines: gastric adenocarcinoma, lung cancer, bladder carcinoma and leukemia. Assuming the mechanism of action by topoisomerase II binding model, the compounds possessing the greatest activity had nonpolar side-chain into hydrophobic binding region on the DNA/topo II complex. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C
  作者：Brigitte E.A. Burm、Michaël M. Meijler、Jacco Korver、Martin J. Wanner、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4020(98)00306-8

  日期：1998.5

  brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist between the trans- and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate

  描述了从6-溴-（N-甲基）色胺的直接合成溴化海洋生物碱阿糖胞苷A（1），B（2）和C（3）的方法。的平衡，碱性和酸性条件下被发现之间存在反式-和顺式-异构体3和4。光谱数据表明，异构体4的结构与最近从海洋被膜植物假单胞菌假单胞菌中分离出的鉴定为阿糖胞苷D的化合物不符。