N-palmitoyltryptamine | 21469-15-8

• 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: N-palmitoyltryptamine
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]hexadecanamide；N-(2-indol-3-yl-ethyl)-palmitamide；N-(2-Indol-3-yl-aethyl)-palmitamid
• CAS: 21469-15-8
• 化学式: C₂₆H₄₂N₂O
• 分子量: 398.632
• InChiKey: YZWBXGMMZOEBAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-palmitoyltryptamine 在 三氯氧磷 作用下， 生成 1-pentadecyl-4,9-dihydro-3H-β-carboline
  参考文献：
  名称：

  Hahn; Gudjons, Chemische Berichte, 1938, vol. 71, p. 2175,2181

  摘要：

  DOI：
• 作为产物：
  描述：

  棕榈酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N-palmitoyltryptamine
  参考文献：
  名称：

  Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide

  摘要：

  DOI：

  10.1016/s0040-4039(00)71520-6

文献信息

• Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons
  作者：Fanny Schmidt、Gael Le Douaron、Pierre Champy、Majid Amar、Blandine Séon-Méniel、Rita Raisman-Vozari、Bruno Figadère

  DOI：10.1016/j.bmc.2010.05.067

  日期：2010.7

  the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest

  ñ-脂肪酰基类色胺构成了主要在无核植物中遇到的一种稀有天然化合物。迄今为止，尚未报道这些稀有分子的生物活性。这项研究调查了这些天然色胺酮衍生物在原发性中脑培养物中对多巴胺能（DA）神经元的神经营养特性。结构-活性关系研究使我们精确地确定了氮原子在脂族链中的作用，赋予了化合物以纳摩尔级的组合的神经保护和神经生成活性。这些天然产物的有效抗氧化活性似乎与它们的作用机理有关。这项研究首次对番荔枝科提取物中存在的天然神经营养因子模拟物进行了首次描述，并导致了化合物的生物学表征，
• Identification and isolation of insecticidal oxazoles from <i>Pseudomonas</i> spp.
  作者：Florian Grundmann、Veronika Dill、Andrea Dowling、Aunchalee Thanwisai、Edna Bode、Narisara Chantratita、Richard ffrench-Constant、Helge B Bode

  DOI：10.3762/bjoc.8.85

  日期：——

  Two new and five known oxazoles were identified from two different Pseudomonas strains in addition to the known pyrones pseudopyronine A and B. Labeling experiments confirmed their structures and gave initial evidence for a novel biosynthesis pathway of these natural oxazoles. In order to confirm their structure, they were synthesized, which also allowed tests of their bioactivity. Additionally, the bioactivities of the synthesis intermediates were also investigated revealing interesting biological activities for several compounds despite their overall simple structures.

  从两种不同的假单胞菌菌株中鉴定出了两种新的和五种已知的噁唑，此外还有已知的吡喃类化合物伪吡喃A和B。标记实验证实了它们的结构，并初步证明了这些天然噁唑的新生物合成途径。为了确认它们的结构，它们被合成，这也允许对它们的生物活性进行测试。此外，还对合成中间体的生物活性进行了调查，揭示了几种化合物尽管结构简单，但具有有趣的生物活性。
• First reported propylphosphonic anhydride (T3P®) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
  作者：Tímea Szabó、András Dancsó、Péter Ábrányi-Balogh、Balázs Volk、Mátyás Milen

  DOI：10.1016/j.tetlet.2019.04.024

  日期：2019.5

  In the present work, a propylphosphonic anhydride (T3P®) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitrile under microwave irradiation, and the product isolation required only an extraction and subsequent crystallization; no chromatography was necessary. The desired

  在目前的工作中，丙基膦酸酐（T3P ®）辅助的罗宾逊-加布里埃尔环化Ñ酰基-β-oxotryptamines为2-取代-5-（3-吲哚基）恶唑已经开发的合成。在微波辐射下，反应在乙腈中顺利进行，产物的分离仅需萃取并随后结晶。无需层析。以良好至优异的产率获得了所需的产物。
• Nagao, Yoshimitsu; Seno, Kaoru; Kawabata, Kohji, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2687 - 2699
  作者：Nagao, Yoshimitsu、Seno, Kaoru、Kawabata, Kohji、Miyasaka, Tadao、Takao, Sachiko、Fujita, Eiichi

  DOI：——

  日期：——
• Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
  作者：Marlene Espinoza-Moraga、Tania Petta、Marco Vasquez-Vasquez、V. Felipe Laurie、Luis A.B. Moraes、Leonardo Silva Santos

  DOI：10.1016/j.tetasy.2010.06.036

  日期：2010.8

  beta-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C-1-C-11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C-15 and higher aliphatic, and aromatic substituted B-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed. (C) 2010 Elsevier Ltd. All rights reserved.