2-isopropyltryptamine | 1338383-40-6

• 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: 2-isopropyltryptamine
• 英文别名: 2-(2-propan-2-yl-1H-indol-3-yl)ethanamine
• CAS: 1338383-40-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: GESHDSJOODJTQK-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±27.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-isopropyltryptamine 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 生成 N-methyl-2-isopropyltryptamine
  参考文献：
  名称：

  Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine

  摘要：

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.

  DOI：

  10.1021/jm200834x
• 作为产物：
  描述：

  2-异丙基-1H-吲哚 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-isopropyltryptamine
  参考文献：
  名称：

  Deconstruction of the α4β2 Nicotinic Acetylcholine Receptor Positive Allosteric Modulator Desformylflustrabromine

  摘要：

  Desformylflustrabromine (dFBr; 1), perhaps the first selective positive allosteric modulator of alpha 4 beta 2 neuronal nicotinic acetylcholine (nACh) receptors, was deconstructed to determine which structural features contribute to its actions on receptors expressed in Xenopus ooycytes using two-electrode voltage clamp techniques. Although the intact structure of 1 was found to be optimal, several deconstructed analogs retained activity. Neither the 6-bromo substituent nor the entire 2-position chain is required for activity. In particular, reduction of the olefinic side chain of 1, as seen with 6, not only resulted in retention of activity/potency but in enhanced selectivity for alpha 4 beta 2 versus alpha 7 nACh receptors. Pharmacophoric features for the allosteric modulation of alpha 4 beta 2 nACh receptors by 1 were identified.

  DOI：

  10.1021/jm200834x

文献信息

• [DE] SUBSTITUIERTE 2-OXO-ALKANSÄURE-[2-(INDOL-3-YL)-ETHYL]AMIDE<br/>[EN] SUBSTITUTED 2-OXO-ALKANOIC ACID-[2-(INDOL-3-YL)-ETHYL] AMIDES<br/>[FR] ACIDE ALCANE-2-OXO-[2-(INDOL-3-YL)-ETHYL]AMIDES SUBSTITUES
  申请人：BAYER AKTIENGESELLSCHAFT

  公开号：WO1999054301A1

  公开（公告）日：1999-10-28

  (DE) Die Erfindug betrifft neue substituierte 2-Oxo- alkansäure-[2- (indol-3-yl) ethyl]-amide der allgemeinen Formel (I), in welcher R1 für gegebenenfalls verzweigtes C1-C8-Alkyl oder C4-C8-Cycloalkyl steht, R2 unabhängig von R3 für Wasserstoff, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Thioalkyl, Phenyl oder Halogen steht, R3 für Wasserstoff, C1-C4-Alkyl oder Halogen steht und R4 für gegebenenfalls verzweigtes C1-C6-Alkyl, C4-C6-Cycloalkyl, gegebenenfalls ein- bis dreifach durch C1-C3-Alkyl, C1-C3-Alkoxy, C1-C3-Thioalkyl, Halogen, Nitro oder Amino substituiertes Phenyl oder gegebenenfalls ein- bis dreifach durch C1-C3-Alkyl, C1-C3-Alkoxy, C1-C3-Thioalkyl, Halogen, Nitro oder Amino substituiertes Benzyl steht, Verfahren zu ihrer Herstellung und ihre Verwendung in antibakteriellen Mitteln.(EN) The invention relates to novel substituted 2-oxo- alkanoic acid-[2- (indol-3-yl)- ethyl] amides of general formula (I), wherein R1 represents optionally branched C1-C8-alkyl or C4-C8-cycloalkyl, R2 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-thioalkyl, phenyl or halogen independently of R3, R3 represents hydrogen, C1-C4-alkyl or halogen and R4 represents optionally branched C1-C6-alkyl or C4-C6-cycloalkyl, phenyl which has been optionally substituted once to three times by C1-C3-alkyl, C1-C3-alkoxy, C1-C3-thioalkyl, halogen, nitro or amino or benzyl which has been optionally substituted once to three times by C1-C3-alkyl, C1-C3-alkoxy, C1-C3-thioalkyl, halogen, nitro or amino. The invention also relates to methods for producing the inventive compounds and to the use of said compounds in antibacterial agents.(FR) L'invention concerne de nouveaux acide alcane-2-oxo[2-(indol-3-yl)-éthyl]amides correspondant à la formule générale (I), dans laquelle: R1 représente alkyle C1-C8 éventuellement ramifié ou cycloalkyle C4-C8; R2 représente, indépendamment de R3, hydrogène, alkyle C1-C4, alcoxy C1-C4, phényle ou halogène; R3 représente hydrogène, alkyle C1-C4 ou halogène; et R4 représente alkyle C1-C6 éventuellement ramifié, cycloalkyle C4-C6, phényle éventuellement substitué d'une à trois fois par alkyle C1-C3, alcoxy C1-C3, thioalkyle C1-C3, halogène, nitro ou amino, ou bien benzyle éventuellement substitué d'une à trois fois par alkyle C1-C3, alcoxy C1-C3, thioalkyle C1-C3, halogène, nitro ou amino. L'invention concerne également un procédé de production de ces composés et leur utilisation dans des agents antibactériens.

  (DE) 概括：本发明涉及一种新型的取代基2-羟基乙二醇酸-[2-(苯并imidazole-3-yl)-甲基]酰胺，其通用化学式为(I)，其中：R1表示可为分支C1-C8-烷基或C4-C8-环烷基的替代基团；R2表示氢、C1-C4烷基、C1-C4羟基、C1-C4硫代烷基、苯基或卤素（在R3中是独立的）；R3表示氢、C1-C4烷基或卤素；R4表示可为分支C1-C6-烷基或C4-C6-环烷基的替代基团，当苯基或甲苯基（这种基团如果有取代基，则为一次取代或三次取代的C1-C3-烷基、C1-C3羟基、C1-C3硫代烷基、卤素、硝基或氨基）；该发明还涉及制备此类化合物的方法，以及该类化合物在抗生素药物中的应用。(EN) This invention relates to novel substituted 2-oxo- alkanoic acid-[2- (indol-3-yl)- ethyl] amides of general formula (I), wherein R1 represents optionally branched C1-C8-alkyl or C4-C8-cycloalkyl, R2 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-thioalkyl, phenyl or halogen independently of R3, R3 represents hydrogen, C1-C4-alkyl, or halogen, and R4 represents optionally branched C1-C6-alkyl or C4-C6-cycloalkyl, phenyl which has been optionally substituted once to three times by C1-C3-alkyl, C1-C3-alkoxy, C1-C3-thioalkyl, halogen, nitro or amino or benzyl which has been optionally substituted once to three times by C1-C3-alkyl, C1-C3-alkoxy, C1-C3-thioalkyl, halogen, nitro or amino. The invention also relates to methods for producing the inventive compounds and to the use of said compounds in antibacterial agents. (FR) L'invention concerne de nouveaux acide alcane-2-oxo[2-(indol-3-yl)-éthyl]amides correspondant à la formule générale (I), dans laquelle: R1 représente alkyle C1-C8 éventuellement ramifié ou cycloalkyle C4-C8; R2 représente, indépendamment de R3, hydrogène, alkyle C1-C4, alcoxy C1-C4, phényle ou halogène; R3 représente hydrogène, alkyle C1-C4 ou halogène; et R4 représente alkyle C1-C6 éventuellement ramifié, cycloalkyle C4-C6, phényle éventuellement substitué d'une à trois fois par alkyle C1-C3, alcoxy C1-C3, thioalkyle C1-C3, halogène, nitro ou amino, ou bien benzyle éventuellement substitué d'une à trois fois par alkyle C1-C3, alcoxy C1-C3, thioalkyle C1-C3, halogène, nitro ou amino. L'invention concerne также un procédé de production de ces composés et leur utilisation dans des agents antibactériens.
• 10.1039/d4sc02802c
  作者：Xie, Kejing、Shen, Zeyuan、Cheng, Peng、Dong, Haoxiang、Yu, Zhi-Xiang、Zu, Liansuo

  DOI：10.1039/d4sc02802c

  日期：——

  The Pictet–Spengler type condensation of tryptamine derivatives and aldehydes or ketones is a classic reaction, and has been previously applied to assemble indole-annulated 5-, 6- and 8-membered heterocyclic rings. In this work, we further expand the synthetic scope of this reaction to the 7-membered azepino[4,5-b]indole skeleton through the direct C–H functionalization of 2-alkyl tryptamines, in which

  色胺衍生物与醛或酮的 Pictet-Spengler 型缩合是一个经典反应，之前已被应用于组装吲哚环 5、6 和 8 元杂环。在这项工作中，我们通过2-烷基色胺的直接C-H官能化，进一步将该反应的合成范围扩展到7元氮杂[4,5- b ]吲哚骨架，其中未活化的亚甲基参与与醛形成7元环。通过将这种前所未有的成环过程与同一碳上的第二次 C-H 烯化相结合，实现了天然产物 ngouniensines 的简明全合成，证明了所开发的化学在简化逆合成断开方面的合成潜力。
• N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：BAYER AG

  公开号：EP0201735B1

  公开（公告）日：1990-09-12
• SUBSTITUIERTE 2-OXO-ALKANSÄURE- 2-(INDOL-3-YL)-ETHYL]AMIDE
  申请人：BAYER AG

  公开号：EP1071664A1

  公开（公告）日：2001-01-31
• US4774240A
  申请人：——

  公开号：US4774240A

  公开（公告）日：1988-09-27