5,6-Methylendioxy-tryptamin | 4388-74-3

• 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: 5,6-Methylendioxy-tryptamin
• 英文别名: 5,6-Methylendioxytryptamin；2-(5H-[1,3]dioxolo[4,5-f]indol-7-yl)ethanamine
• CAS: 4388-74-3
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: BAZNPMXOPKJJQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-Methylendioxy-tryptamin 在 盐酸 、 manganese(IV) oxide 、 5%-palladium/activated carbon 、 sodium hydride 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(6-methyl-5H-[1,3]dioxolo[4,5-f]pyrido[3,4-b]indol-5-yl)butan-1-amine
  参考文献：
  名称：

  Structure–activity relationship study of beta-carboline derivatives as haspin kinase inhibitors

  摘要：

  Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.028
• 作为产物：
  描述：

  7-(2-nitrovinyl)-5H-[1,3]dioxolo[4,5-f]indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 5,6-Methylendioxy-tryptamin
  参考文献：
  名称：

  Structure–activity relationship study of beta-carboline derivatives as haspin kinase inhibitors

  摘要：

  Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.028

文献信息

• [EN] PHENETHYLAMIDE DERIVATIVES AND THEIR HETEROCYCLIC ANALOGUES<br/>[FR] DÉRIVÉS DE PHÉNÉTHYLAMIDE ET LEURS ANALOGUES HÉTÉROCYCLIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2010044054A1

  公开（公告）日：2010-04-22

  The invention relates to novel phenethylamide derivatives and their heterocyclic analogues of formula (I), wherein A, B, R1, R2 and R3 are as described in the application, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.

  这项发明涉及新型苯乙酰胺衍生物及其异环类似物，其化学式为(I)，其中A、B、R1、R2和R3如申请中所述，并且涉及将这种化合物或这种化合物的药用可接受盐用作药物，特别是促进睡眠的药物受体拮抗剂。
• First Total Synthesis of the Proposed Structures of Orisuaveolines A and B
  作者：Jie Zhang、Shijun Da、Xiaolin Feng、Xiaoyi Chen、Jianhui Jiang、Ying Li

  DOI：10.1002/cjoc.201200986

  日期：2013.1

  First total synthesis of the proposed structures of β‐indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet‐Spengler reaction to build a six‐member lactam which further transformed into target molecular by a one‐pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient

  首次报道了拟议的β-吲哚并喹唑啉生物碱orisuaveooline A和B的结构的全合成。合成的关键步骤包括Pictet-Spengler反应以构建六元内酰胺，然后通过一锅缩合进一步转化为目标分子。该合成提供了从便宜的可商购的起始原料以短而方便的方式接近拟南芥酸A和B的结构的方法。我们的合成产物的结构已通过2D-NMR实验确认。
• 10.1021/acschemneuro.4c00060
  作者：Zhao, Yuting、Peng, Yan、Wei, Xiuzhen、Wu, Genping、Li, Bo、Li, Xuelin、Long, Lin、Zeng, Jing、Luo, Wei、Tian, Ying、Wang, Zhen、Peng, Xue

  DOI：10.1021/acschemneuro.4c00060

  日期：——

  drugs are currently available. Previous results showed that N-salicyloyl tryptamine derivatives had the potential to constrain the neuroinflammatory process. In this study, 30 new N-salicyloyl tryptamine derivatives were designed and synthesized to investigate a structure–activity relationship (SAR) for the indole ring of tryptamine in order to enhance their antineuroinflammatory effects. Among them, both

  神经炎症是加剧神经退行性疾病（NDD）中神经元死亡和突触功能异常的重要因素。由于发病机制复杂，且存在血脑屏障（BBB），目前临床尚无有效药物。先前的结果表明， N-水杨酰色胺衍生物具有抑制神经炎症过程的潜力。在本研究中，设计并合成了30种新的N-水杨酰色胺衍生物，以研究色胺吲哚环的构效关系（SAR），以增强其抗神经炎症作用。其中，化合物18在体外和体内均通过抑制小胶质细胞的激活而发挥最佳的抗神经炎症作用，而小胶质细胞是神经炎症的罪魁祸首。其抗神经炎症作用的潜在机制可能与抑制信号转导子和转录激活子3（STAT3）的转录、表达和磷酸化有关，随后调节下游环氧合酶-2（COX-2）的表达和活性。凭借其优异的血脑屏障通透性和药代动力学特性，化合物18对脂多糖（LPS）诱导的小鼠海马区表现出比以前的N-水杨酰色胺衍生物L7显着的神经保护作用。总之，化合物18为开发靶向小胶质细胞激活的高效抗神经炎症治疗药物提供了新途径。
• Adlerova,E. et al., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 784 - 796
  作者：Adlerova,E. et al.

  DOI：——

  日期：——
• 5-Fluortryptamin und weitere neue Bz-substituierte Tryptamine
  作者：M. Protiva、E. Adlerová、Z. J. Vejdělek、L. Novák、M. Rajšner、I. Ernest

  DOI：10.1007/bf00632308

  日期：1959.1