5-methoxy-3-[2-(N-acetylamino)ethyl]indol-2(3H)-one | 188397-16-2

• 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: 5-methoxy-3-[2-(N-acetylamino)ethyl]indol-2(3H)-one
• 英文别名: N-[2-(5-methoxy-2-oxo-2,3-dihydro-1H-indol-3-yl)ethyl]acetamide；N-[2-(5-methoxy-2-oxoindolin-3-yl)ethyl]acetamide；2-oxo-2,3-dihydromelatonin；N-[2-(5-methoxy-2-oxo-2,3-dihydroindol-3-yl)ethyl]-acetamide；2-Oxomelatonin；N-[2-(5-methoxy-2-oxo-1,3-dihydroindol-3-yl)ethyl]acetamide
• CAS: 188397-16-2
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: HNEAVHQAQROOMN-UHFFFAOYSA-N

物化性质

• 沸点：
  502.8±50.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-[2-(N-acetylamino)ethyl]indol-2(3H)-one 在 乙酸酐 作用下， 以 苯 为溶剂， 生成 N-[2-(1-acetyl-2-oxo-5-methoxy-2,3-dihydroindol-3-yl)-ethyl]acetamide
  参考文献：
  名称：

  US6004991

  摘要：

  公开号：
• 作为产物：
  描述：

  褪黑素 在 盐酸 、 ammonium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 5-methoxy-3-[2-(N-acetylamino)ethyl]indol-2(3H)-one
  参考文献：
  名称：

  Oxidation derivatives of indolylalkylamines and their use as drugs

  摘要：

  该发明涉及一般式I的衍生物。该发明还涉及包含一般式I的药用和化妆品组合物。

  公开号：

  US06066663A1

文献信息

• Simple Synthesis of Some 2-Substituted Melatonin Derivatives
  作者：Natalia Lozinskaya、Sergey Sosonyuk、Maria Volkova、Michael Seliverstov、Marina Proskurnina、Sergey Bachurin、Nikolay Zefirov

  DOI：10.1055/s-0030-1258361

  日期：2011.1

  synthesis of some 2-substituted melatonin derivatives using p-anisidine as starting material is reported. The key step is a chemoselective reduction of a cyano group in the presence of an appropriate acid anhydride by hydrogenation over Adams’ catalyst or with sodium borohydride in the presence of catalytic amounts of anhydrous nickel(II) chloride. The 2-substituted melatonin derivatives were obtained

  报道了一种使用对茴香胺作为起始原料合成某些2-取代的褪黑激素衍生物的简单策略。关键步骤是在适当的酸酐存在下，通过在Adams催化剂上氢化或在催化量的无水氯化镍（II）存在下用硼氢化钠进行化学选择性还原氰基。2-取代的褪黑激素衍生物以六到七个步骤从廉价的对茴香胺中以9-13％的总产率获得。 吲哚-褪黑激素衍生物-还原-药物化学
• Acyl derivatives of melatonin and of melatoninergic analogues and their
  申请人：Cemaf and Laboratories Besins Isovesco S.A.

  公开号：US06140372A1

  公开（公告）日：2000-10-31

  The invention relates to derivatives of general formula I ##STR1## as defined in the description. The invention also relates to a process for their preparation and to their therapeutic use, in particular for the treatment of complaints associated with melatonin disorders, and pharmaceutical and cosmetic compositions comprising them.

  该发明涉及一般式I的衍生物，如描述中所定义。该发明还涉及它们的制备过程及其治疗用途，特别是用于治疗与褪黑激素失调相关的疾病，并包括它们的制药和化妆品组合物。
• Synthesis of New 2,3-Dihydroindole Derivatives and Evaluation of Their Melatonin Receptor Binding Affinity
  作者：Maria S. Volkova、Alexander M. Efremov、Elena N. Bezsonova、Michael D. Tsymliakov、Anita I. Maksutova、Maria A. Salykina、Sergey E. Sosonyuk、Elena F. Shevtsova、Natalia A. Lozinskaya

  DOI：10.3390/molecules27217462

  日期：——

  3-Dihydroindoles are promising agents for the synthesis of new compounds with neuroprotective and antioxidant properties. Usually, these compounds are obtained by direct reduction of the corresponding indoles containing acceptor groups in the indole ring for its activation. In this work, we propose a synthetic strategy to obtain new 2,3-dihydroindole derivatives from the corresponding polyfunctional 2-oxindoles

  2,3-二氢吲哚是合成具有神经保护和抗氧化特性的新化合物的有前景的试剂。通常，这些化合物是通过将相应的吲哚环上含有受体基团的吲哚直接还原活化而得到的。在这项工作中，我们提出了一种合成策略，从相应的多官能 2-羟吲哚中获得新的 2,3-二氢吲哚衍生物。提出了三种使用各种硼氢化物还原 2-羟吲哚和 2-氯吲哚分子中官能团的方法。显示了在酰胺存在下化学选择性还原腈基的可能性。例如，所提出的合成策略可用于合成内源性激素褪黑激素和其他具有神经保护特性的化合物的新类似物。
• Further insights into the reaction of melatonin with hydroxyl radical
  作者：Joseph A. Horstman、Monika Z. Wrona、Glenn Dryhurst

  DOI：10.1016/s0045-2068(02)00511-4

  日期：2002.10

  Recent interest has focused on the use of exogenous melatonin as an antioxidant, particularly to scavenge the highly cytotoxic hydroxyl radical (HO.) which may be generated in many pathological conditions. However, in vitro and in vivo studies aimed at assessing the antioxidant properties of melatonin have produced conflicting results. While it is known that HO, reacts with melatonin at a diffusion limited rate, very little is known about the products of this reaction. In this investigation it is shown that incubation of melatonin with a Fenton-type HO.-generating system at pH 7.4 forms a complex mixture of primary products. These include 2-hydroxymelatonin, which was isolated as its more stable oxindole tautomer, 4- and 6-hydroxymelatonin, N-acetyl-N-2-formyl-5-methoxykynurenine and 7,7'-bi-(5-methoxy-N-acetyltryptamine-4-one). Reaction pathways that might lead to these products are described. The differing biological effects of these products, while currently incompletely understood, might account for the controversy concerning the antioxidant properties of melatonin. (C) 2002 Published by Elsevier Science (USA).
• US06004991
  申请人：——

  公开号：——

  公开（公告）日：——