N-(2-(1H-indol-3-yl)ethyl)heptanamide | 21469-23-8

• 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-(2-(1H-indol-3-yl)ethyl)heptanamide
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]heptanamide
• CAS: 21469-23-8
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: KZBBIEIJSXSFOC-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  512.8±33.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)heptanamide 在 三乙基硅烷 、 sodium tungstate 、 双氧水 作用下， 以 甲醇 、 水 、 三氟乙酸 为溶剂， 反应 2.0h， 生成 N-heptanoyl-1-hydroxytryptamine
  参考文献：
  名称：

  The Ideal Synthetic Method Aimed at the Leads for an a2-Blocker, an Inhibitor of Blood Platelet Aggregation, and an Anti-osteoporosis Agent

  摘要：

  According to the definition of the ideal synthetic method, an example aimed at the leads for an alpha(2)-blocker, an inhibitor of platelet aggregation, and an anti-osteoporosis agent is established starting from tryptamine. The originality rate, the intellectual property, and the application potential factors of the method are 71, 54, and 100, respectively. The method employs only conventional reagents and reaction conditions without using any protecting groups.

  DOI：

  10.3987/com-06-10771
• 作为产物：
  描述：

  色胺 、 庚酸 在 4,6-dichloro-1,3,5-triazin-2-yl-NH-PEG-polystyrene 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 N-(2-(1H-indol-3-yl)ethyl)heptanamide
  参考文献：
  名称：

  Solid-Supported Chloro[1,3,5]triazine. A Versatile New Synthetic Auxiliary for the Synthesis of Amide Libraries

  摘要：

  [GRAPHICS]2,4,6-Trichloro[1,3,5]triazine was loaded on different types of NH2-functional resins to give a new supported reagent. The best results, in term of yields products, were obtained using the chlorotriazine linked to a polystyrene-poly(ethylene glycol) resin. This reagent was employed for the solution-phase synthesis of different amides and dipeptides.

  DOI：

  10.1021/ol990215h

文献信息

• Insecticidal activity of indole derivatives against Plutella xylostella and selectivity to four non-target organisms
  作者：Ângela C. F. Costa、Sócrates C. H. Cavalcanti、Alisson S. Santana、Ana P. S. Lima、Thaysnara B. Brito、Rafael R. B. Oliveira、Nathália A. Macêdo、Paulo F. Cristaldo、Ana Paula A. Araújo、Leandro Bacci

  DOI：10.1007/s10646-019-02095-1

  日期：2019.10

  have resistance to a range of insecticides. Indole derivates can exert diverse biological activities, and different effects may be obtained from small differences in their molecular structures. Indole is the parent substance of a large number of synthetic and natural compounds, such as plant and animal hormones. In the present study, we evaluate the insecticidal activity of 20 new synthesized indole

  小菜蛾小菜蛾（小菜蛾，Linnaeus，1758年）（鳞翅目：Plutellidae）是经济上具有重要意义的芸苔属作物的杀虫剂，对多种杀虫剂具有抗性。吲哚衍生物可以发挥多种生物活性，并且从它们的分子结构上的微小差异可以获得不同的效果。吲哚是许多合成和天然化合物（例如植物和动物激素）的母体。在本研究中，我们评估了20种新合成的吲哚衍生物对小菜蛾的杀虫活性，以及​​这些衍生物对非目标膜翅目有益节肢动物的选择性：传粉媒介Apis mellifera（Linnaeus，1758）（Hymenoptera：Apidae），和捕食者Polybia scutellaris（怀特，1841年），polybia sericea（Olivier，1791年）和Polybia rejecta（Fabricius，1798年）（膜翅目：维斯皮科）。在实验室中进行了生物测定，以确定化合物对小菜蛾的致死作用和亚致死作
• 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。
• Synthesis, Activity, and QSAR Studies of Tryptamine Derivatives on Third-instar Larvae of Aedes Aegypti Linn
  作者：Rafael Oliveira、Thaysnara Brito、Angelita Nepel、Emmanoel Costa、Andersson Barison、Rogeria Nunes、Roseli Santos、Socrates Cavalcanti

  DOI：10.2174/1573406409666131202144010

  日期：2014.8.4

  Special attention has been given to the mosquito Aedes aegypti Linn. (Diptera: Culicidae) owing to numerous dengue epidemic outbreaks worldwide. Failure to control vector spreading is accounted for unorganized urban growth and resistance to larvicides and insecticides. Therefore, researchers are currently searching for new and more efficient larvicides and insecticides to aid dengue control measures. Triptamine is known to affect insect behavior, development, and physiology. Expression of this compound in plants has reduced the growth rate of herbivore insects. In view of these facts, it was of our interest to synthesize triptamine amide derivatives as potential larvicides against Ae. aegypti, establishing a Structure-Activity Relationship. Eleven amide derivatives of triptamine were synthesized, characterized, and evaluated for their larvicidal activity against third-instar Ae. aegypti larvae. N-(2-(1H-indol-3-yl)ethyl)-2,2,2-trichloroacetamide exhibited the highest overall larvicidal potency, while N-(2-(1H-Indol-3-yl)ethyl) acetamide displayed the lowest larvicidal potency. A regression equation correlating the larvicidal activity with Log P was obtained. We have found a clear relationship between the larvicidal activity of non-chlorinated compounds and Log P. Analysis of the relationship between Log P and larvicidal activity against Ae. aegypti may be useful in the evaluation of potential larvicidal compounds.

  埃及伊蚊受到了特别关注。 （双翅目：蚊科）由于许多 登革热疫情在全球爆发。未能控制病媒传播是造成无组织城市增长和 对杀幼虫剂和杀虫剂的抗性。因此，研究人员目前正在寻找新的、更有效的杀幼虫剂 和杀虫剂以协助登革热控制措施。已知曲巴胺会影响昆虫的行为、发育和 生理。这种化合物在植物中的表达降低了食草昆虫的生长速度。鉴于这些事实， 我们感兴趣的是合成曲巴胺酰胺衍生物作为潜在的抗伊蚊幼虫剂。埃及伊蚊，建立 结构-活性关系。合成、表征并评估了 11 种曲巴胺的酰胺衍生物 它们对三龄伊蚊的杀幼虫活性。埃及伊蚊幼虫。 N-(2-(1H-吲哚-3-基)乙基)-2,2,2-三氯乙酰胺表现出 总体杀幼虫效力最高，而 N-(2-(1H-吲哚-3-基)乙基)乙酰胺显示出最低的杀幼虫效力。 获得了将杀幼虫活性与Log P 相关的回归方程。我们已经找到了明确的关系 非氯化物杀幼虫活性与 Log P 之间的关系。Log P 之间的关系分析 和针对伊蚊的杀幼虫活性。埃及伊蚊可能有助于评估潜在的杀幼虫化合物。
• Synthesis of Nb-Acyltryptamines and Their 1-Hydroxy-tryptamine Derivatives as New α2-Blockers
  作者：Masanori Somei、Koji Yamada、Yoshio Tanaka

  DOI：10.3987/com-08-s(d)29

  日期：——

  N-b-Acyl- and N-b-acyl-1-hydroxytryptamines are found to be novel and structurally simple alpha(2)-blocker for the treatment of erectile dysfunction.
• Receptor Blocker and Vasodilator Comprising Indole Derivative as Active Ingredient
  申请人：Somei Masanori

  公开号：US20090005430A1

  公开（公告）日：2009-01-01

  It is intended to find a compound that is structurally simpler than yohimbine, a pentacyclic condensed heterocyclic compound, and has an effect similar to that of yohimbine. The present invention relates to a pharmaceutical or food composition for α 2 receptor blockage comprising a compound represented by the formula (I) or a pharmaceutically acceptable salt thereof: (wherein R 1 represents a hydrogen, alkyl group, alkenyl group, alkynyl group, aromatic group, aralkyl group, acyl group, arylsulfonyl group, alkylsulfonyl group, or hydroxyl group; R 2 represents a hydrocarbon group; R 3 , R 4 , R 5 , R 6 , and R 7 are the same or different and represent a hydrogen, halogen, alkyl group, or alkoxy group; R 8 represents a hydrogen or acyl group; n represents an integer of 1 to 6; and a and b are the same or different and represent 1 or 0).