N-[2-(1H-indol-3-yl)ethyl]-3-methylbutanamide

• 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]-3-methylbutanamide
• 英文别名: N¹²-isovaleryltryptamine；Tryptamine isovalerate
• 化学式: C₁₅H₂₀N₂O
• 分子量: 244.337
• InChiKey: TXVZEMGYXBGIEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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]-3-methylbutanamide 在 四氯化碳 、 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 六氯乙烷 、 三乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-chloro-5-(1H-indol-3-yl)-2-isobutyloxazole
  参考文献：
  名称：

  A Concise and Rapid Approach to the Marine Natural Product Streptochlorin and its Analogues

  摘要：

  DOI：

  10.5012/bkcs.2013.34.2.357
• 作为产物：
  描述：

  异戊酸 、 色胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[2-(1H-indol-3-yl)ethyl]-3-methylbutanamide
  参考文献：
  名称：

  Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)

  摘要：

  Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe beta-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.003

文献信息

• 苯并杂环类化合物及其制备方法和用途
  申请人：中国科学院上海药物研究所

  公开号：CN103601683B

  公开（公告）日：2016-03-30

  本发明提供一类非核苷类抗病毒抑制剂，具体为如通式I所示的苯并杂环类化合物或其药学上可接受的盐或水合物，本发明还提供了该类化合物或其药学上可接受的盐或水合物的制备方法。经药理试验表明该类化合物或其药学上可接受的盐或水合物能有效抑制乙肝病毒DNA复制和丙肝病毒RNA复制，因此本发明还提供了该类化合物在制备预防和/或治疗病毒性感染、特别是乙肝病毒(HBV)感染和丙肝病毒(HCV)感染的药物中的用途。
• Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (−)-coerulescine and (−)-horsfiline by oxidative rearrangement
  作者：Manda Sathish、Fabiane M. Nachtigall、Leonardo S. Santos

  DOI：10.1039/d0ra07705d

  日期：——

  (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (−)-coerulescine (5) and (−)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.

  四氢-β-咔啉（THBC）是一种三环系统，存在于大量生物活性生物碱中。在此，我们报告了一种通过手性硫代酰胺（ 11b ）催化亚胺还原二氢-β-咔啉（ 17a-f ）合成对映体纯THBC的简单有效的方法。原位生成的 Pd-H 在不同取代的手性 THBC ( 18a-f ) 反应中用作氢化物源，具有高选择性（ R异构体，高达 96% ee）和良好的分离收率（高达 88%）。此外，所使用的手性硫代方酰胺还在 (−)-coerulescine ( 5 ) 和 (−)-horsfiline ( 6 ) 的合成中提供了优异的催化剂活性，通过对映选择性氧化，其对映选择性优异，分别高达 98% 和 93% ee重排方法。
• 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。
• 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。