2-(1-苄基-1H-吲哚-3-基)-2-氧代乙酰胺 | 108977-91-9

• 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
• 中文名称: 2-(1-苄基-1H-吲哚-3-基)-2-氧代乙酰胺
• 英文名称: 2-(1-benzyl-1H-indol-3-yl)-2-oxoacetamide
• 英文别名: 2-(1-benzylindol-3-yl)-2-oxoacetamide
• CAS: 108977-91-9
• 化学式: C₁₇H₁₄N₂O₂
• mdl: MFCD06619266
• 分子量: 278.31
• InChiKey: HLOOTINKQNUIQY-UHFFFAOYSA-N

物化性质

• 沸点：
  525.3±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-(1-苄基-1H-吲哚-3-基)-2-氧代乙酰胺 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 25.0h， 以45%的产率得到N-benzyl-2-(1-benzyl-1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives

  摘要：

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.001
• 作为产物：
  描述：

  1-苄基吲哚 在 乙醚 、 氨 作用下， 生成 2-(1-苄基-1H-吲哚-3-基)-2-氧代乙酰胺
  参考文献：
  名称：

  413.育亨宾和相关生物碱的组成。第十二部分。育亨宾和阿司他林的一些合成方法未成功

  摘要：

  DOI：

  10.1039/jr9580002045

文献信息

• Copper(II)-Mediated Aerobic Oxidation of Benzylimidates: Synthesis of Primary α-Ketoamides
  作者：Yogesh Kumar、Mukta Shaw、Rima Thakur、Amit Kumar

  DOI：10.1021/acs.joc.6b01262

  日期：2016.8.5

  A simple and straightforward method for the synthesis of primary α-ketoamides has been discovered. The reaction represents the first example of benzylimidates directly converting to primary α-ketoamides by using sustainable molecular oxygen as an oxidant. This reaction proceeds in the presence of copper(II) salt via cleavage of benzylic C–H and C–O bonds of the benzylimidates with liberation of alcohols

  已经发现一种简单直接的合成伯α-酮酰胺的方法。该反应代表了通过使用可持续的分子氧作为氧化剂将亚氨基苄基酯直接转化为伯α-酮酰胺的第一个例子。该反应在铜盐（II）的存在下通过裂解亚氨酸苄基的苄基C–H和C–O键进行，唯一的副产物是醇的释放。广泛的底物范围，操作温和的条件，使用单个底物以及放大至克数的反应，使得该策略非常具有吸引力和实用性。此外，机理研究表明，与苄基位置相邻的亚氨酸酯基团在促进该化学过程中起着至关重要的作用。
• Formamidine hydrochloride as an amino surrogate: I₂-catalyzed oxidative amidation of aryl methyl ketones leading to free (N–H) α-ketoamides
  作者：Shan Liu、Qinghe Gao、Xia Wu、Jingjing Zhang、Kerong Ding、Anxin Wu

  DOI：10.1039/c4ob02591a

  日期：——

  A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones has been developed. This reaction represents a novel strategy for the synthesis of free (N–H) α-ketoamides.

  已开发出一种高效的分子碘催化的芳基甲基酮氧化酰胺化反应。该反应代表了合成自由(N-H) α-酮酰胺的新颖策略。
• METHOD FOR PREVENTION OR TREATMENT OF METABOLIC SYNDROME
  申请人：Miyazaki, Toru

  公开号：EP2572730A1

  公开（公告）日：2013-03-27

  The present invention aims to provide a method for the prophylaxis or treatment of metabolic syndrome, which can discontinue the domino effect-like chain of diseases in metabolic syndrome in the upstream by suppressing infiltration of macrophage into the adipose tissues. The present invention provides a method for the prophylaxis or treatment of a metabolic syndrome, including a step of administering an AIM inhibitor to a subject.

  本发明旨在提供一种预防或治疗代谢综合征的方法，该方法可通过抑制巨噬细胞向脂肪组织的浸润，从上游阻断代谢综合征多米诺骨牌效应般的疾病链。本发明提供了一种预防或治疗代谢综合征的方法，包括向受试者施用 AIM 抑制剂的步骤。
• 413. The constitution of yohimbine and related alkaloids. Part XII. Some unsuccessful synthetic approaches to yohimbine and alstoniline
  作者：K. B. Prasad、G. A. Swan

  DOI：10.1039/jr9580002045

  日期：——
• Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives
  作者：Sabrina Taliani、Maria Letizia Trincavelli、Barbara Cosimelli、Sonia Laneri、Elda Severi、Elisabetta Barresi、Isabella Pugliesi、Simona Daniele、Chiara Giacomelli、Giovanni Greco、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1016/j.ejmech.2013.09.001

  日期：2013.11

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.