N-(2-(7-methyl-1H-indol-3-yl)ethyl)acetamide | 769186-81-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-(7-methyl-1H-indol-3-yl)ethyl)acetamide
• 英文别名: N-[2-(7-methyl-1H-indol-3-yl)ethyl]acetamide
• CAS: 769186-81-4
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: FOKFBQAIBXFKNP-UHFFFAOYSA-N

物化性质

• 沸点：
  483.9±33.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(7-methyl-1H-indol-3-yl)ethyl)acetamide 在 sodium hypochlorite 作用下， 以 水 、 乙腈 为溶剂， 以86%的产率得到1-(3a-chloro-7-methyl-3,3a-dihydropyrrolo[2,3-b]indol-1(2H)-yl)ethan-1-one
  参考文献：
  名称：

  10.1002/chem.202401436

  摘要：

  An efficient and rapid protocol for the oxidative halogenation of tryptamines with 10% aqueous NaClO has been developed. This reaction is featured by its operational simplicity, metal‐free conditions, no purification, and high yield. Notably, the resulting key intermediates are suitable for further functionalization with various nucleophiles, including amines, N‐aromatic heterocycles, indoles and phenols. The overall transformation exhibits broad functional‐group tolerance and is applicable to the late‐stage functionalization of complex biorelevant molecules.

  DOI：

  10.1002/chem.202401436
• 作为产物：
  描述：

  7-甲基色胺 、 乙酰辅酶A 在 5,5'-二硫双(2-硝基苯甲酸) 、 Drosophila melanogaster arylalkylamine N-acetyltransferase A from E_. coli 作用下， 以 aq. buffer 为溶剂， 生成 N-(2-(7-methyl-1H-indol-3-yl)ethyl)acetamide
  参考文献：
  名称：

  Mechanistic and Structural Analysis of Drosophila melanogaster Arylalkylamine N-Acetyltransferases

  摘要：

  Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N-acetylation of arylalkylamines is a critical step in Drosophila melanogaster for the inactivation of the bioactive amines and the sclerotization of the cuticle. Two AANAT variants (AANATA and AANATB) have been identified in D. melanogaster, in which AANATA differs from AANATB by the truncation of 35 amino acids from the N-terminus. We have expressed and purified both D. melanogaster AANAT variants (AANATA and AANATB) in Escherichia coli and used the purified enzymes to demonstrate that this N-terminal truncation does not affect the activity of the enzyme. Subsequent characterization of the kinetic and chemical mechanism of AANATA identified an ordered sequential mechanism, with acetyl-CoA binding first, followed by tyramine. We used a combination of pH-activity profiling and site-directed mutagenesis to study prospective residues believed to function in AANATA catalysis. These data led to an assignment of Glu-47 as the general base in catalysis with an apparent pKa of 7.0. Using the data generated for the kinetic mechanism, structure-function relationships, pH-rate profiles, and site-directed mutagenesis, we propose a chemical mechanism for AANATA.

  DOI：

  10.1021/bi5006078

文献信息

• Iridium-Catalyzed Direct Synthesis of Tryptamine Derivatives from Indoles: Exploiting N-Protected β-Amino Alcohols as Alkylating Agents
  作者：Silvia Bartolucci、Michele Mari、Annalida Bedini、Giovanni Piersanti、Gilberto Spadoni

  DOI：10.1021/acs.joc.5b00195

  日期：2015.3.20

  The selective C3-alkylation of indoles with N-protected ethanolamines involving the “borrowing hydrogen” strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

  描述了涉及“借用氢”策略的N-保护的乙醇胺对吲哚的选择性C3-烷基化反应。该方法提供了对几种色胺衍生物的方便且可持续的获取途径。
• [EN] MELATONIN DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL DYSFUNCTIONS<br/>[FR] DERIVES DE MELATONINE ET LEUR UTILISATION DANS LE TRAITEMENT DE DYSFONCTIONNEMENTS NEUROLOGIQUES
  申请人：FAUST PHARMACEUTICALS

  公开号：WO2004085392A1

  公开（公告）日：2004-10-07

  The present invention relates to compounds of the general formula (1): wherein R1, R2, R3, R4 and R5 are H or a moiety of the formula : -(R6)n-R7; with R6 is a is an alkyl chain and R7 is, a moiety selected in the group consisting of -Cn,H2n2,+I, a cycloalkyl moiety, -N(Cn,H2n,+I)(Cn,H2n,+1), -NH-cycloalkyl, -O(Cn,H2n'+I), -0-cycloalkyl, =O, =S, -NO2, -I, -Br, -Cl, -F, -CF3, -OCF3, -COOH, -S03H, -P03H2, -CN, A3 and A4 are, C, N,O or S;m is from 0 to 2; and to their use for the treatment and/or prevention of diseases and conditions mediated by the imbalance of acetylcholine, and for treating and/or preventing glutamate excitotoxicity.

  本发明涉及通式（1）的化合物：其中R1、R2、R3、R4和R5为H或具有以下结构的基团：-(R6)n-R7；其中R6是烷基链，R7是在由-CnH2n2，+I组成的基团中选择的一个基团，是环烷基基团，-N(CnH2n+I)(CnH2n+1)，-NH-环烷基，-O(CnH2n'+I)，-O-环烷基，=O，=S，-NO2，-I，-Br，-Cl，-F，-CF3，-OCF3，-COOH，-SO3H，-PO3H2，-CN中的一种；A3和A4为C、N、O或S；m为0到2；以及它们用于治疗和/或预防由乙酰胆碱失衡介导的疾病和症状，以及用于治疗和/或预防谷氨酸兴奋毒性。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR MAKING THE SAME<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS POUR PRÉPARER CEUX-CI
  申请人：SIGNUM BIOSCIENCES INC

  公开号：WO2009132051A1

  公开（公告）日：2009-10-29

  The present invention provides compounds and/or compositions that modulate PP2A methylation and/or activity and methods for preparing the same, which are useful for modulating the demethylation of PP2A, modulating the methylation of PP2 A and/or modulating the activity of PP2A.
• Mechanistic and Structural Analysis of <i>Drosophila melanogaster</i> Arylalkylamine <i>N</i>-Acetyltransferases
  作者：Daniel R. Dempsey、Kristen A. Jeffries、Jason D. Bond、Anne-Marie Carpenter、Santiago Rodriguez-Ospina、Leonid Breydo、K. Kenneth Caswell、David J. Merkler

  DOI：10.1021/bi5006078

  日期：2014.12.16

  Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N-acetylation of arylalkylamines is a critical step in Drosophila melanogaster for the inactivation of the bioactive amines and the sclerotization of the cuticle. Two AANAT variants (AANATA and AANATB) have been identified in D. melanogaster, in which AANATA differs from AANATB by the truncation of 35 amino acids from the N-terminus. We have expressed and purified both D. melanogaster AANAT variants (AANATA and AANATB) in Escherichia coli and used the purified enzymes to demonstrate that this N-terminal truncation does not affect the activity of the enzyme. Subsequent characterization of the kinetic and chemical mechanism of AANATA identified an ordered sequential mechanism, with acetyl-CoA binding first, followed by tyramine. We used a combination of pH-activity profiling and site-directed mutagenesis to study prospective residues believed to function in AANATA catalysis. These data led to an assignment of Glu-47 as the general base in catalysis with an apparent pKa of 7.0. Using the data generated for the kinetic mechanism, structure-function relationships, pH-rate profiles, and site-directed mutagenesis, we propose a chemical mechanism for AANATA.
• 10.1002/chem.202401436
  作者：Xu, Jiayi、Zhang, Yahui、Cai, Qiling、Chen, Li、Sun, Yang、Liu, Qinying、Gao, Yu、Chen, Haijun

  DOI：10.1002/chem.202401436

  日期：——

  An efficient and rapid protocol for the oxidative halogenation of tryptamines with 10% aqueous NaClO has been developed. This reaction is featured by its operational simplicity, metal‐free conditions, no purification, and high yield. Notably, the resulting key intermediates are suitable for further functionalization with various nucleophiles, including amines, N‐aromatic heterocycles, indoles and phenols. The overall transformation exhibits broad functional‐group tolerance and is applicable to the late‐stage functionalization of complex biorelevant molecules.