3-(1H-indol-3-yl)-1-morpholinopropan-1-one | 94028-93-0

• 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: 3-(1H-indol-3-yl)-1-morpholinopropan-1-one
• 英文别名: Propionic acid, 3-indolyl-, morpholide；3-(1H-indol-3-yl)-1-morpholin-4-ylpropan-1-one
• CAS: 94028-93-0
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: QAQKTOGMABHKME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-indol-3-yl)-1-morpholinopropan-1-one 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 正丁基锂 、 二碳酸二叔丁酯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 18.25h， 生成 (E)-3-(1-(di-tert-butylphosphino)-7-styryl-1H-indol-3-yl)-1-morpholinopropan-1-one
  参考文献：
  名称：

  铑催化的PIII-螯合辅助的吲哚C7-羧酸，酸酐/酰化，酰化，甲基化和酰化

  摘要：

  已开发出通过CH和C-C键活化铑催化的C7-选择性脱羰芳基化，吲哚与羧酸或酸酐的吲哚甲基化反应。此外，在开发的系统中，还可以在较低的反应温度下选择性生成C7酰化产物。这一转变的高反应性和区域选择性的关键是吲哚的适当选择Ñ -P吨卜2螯合辅助基团。该方法具有许多优点，包括易于接近和除去导向基团，使用便宜且可广泛获得的偶联剂，不需要外部配体或氧化剂，广泛的底物范围，高效率以及形成唯一的区域异构体。

  DOI：

  10.1002/anie.201813182
• 作为产物：
  描述：

  吗啉 、 3-吲哚丙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(1H-indol-3-yl)-1-morpholinopropan-1-one
  参考文献：
  名称：

  Indole derivatives as potent inhibitors of 5-lipoxygenase: Design, synthesis, biological evaluation, and molecular modeling

  摘要：

  A series of novel indole derivatives was designed, synthesized and evaluated by cell-based assays for their inhibitory activities against 5-LOX in rat peritoneal leukocytes. Most of them (30 out of 35) showed an inhibitory potency higher than the initial screening hit 1a (IC50 = 74 mu M). Selected compounds for concentration-response studies showed prominent inhibitory activities with IC50 values ranging from 0.74 mu M to 3.17 mu M. Four compounds (1m, 1s, 4a, and 6a) exhibited the most potent inhibitory activity compared to that of the reference drug (Zileuton), with IC50 values less than I mu M. Molecular modeling studies for compounds 1a, 3a, 4a, and 6a were also presented. The excellent in vitro activities of this class of compounds may possess potential for the treatment of LT-related diseases. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.02.038

文献信息

• Late-Stage Photoredox C–H Amidation of N-Unprotected Indole Derivatives: Access to <i>N</i>-(Indol-2-yl)amides
  作者：Yue Weng、Bo Ding、Yunqing Liu、Chunlan Song、Lo-Ying Chan、Chien-Wei Chiang

  DOI：10.1021/acs.orglett.1c00609

  日期：2021.4.2

  carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C–H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing

  N-未保护的吲哚的后期功能化可用于修饰低分子量药物和生物活性肽。吲哚羧酰胺在医药应用中很有价值，而具有相似结构的N-（吲哚-2-基）酰胺的制备仍然具有挑战性。本文中我们报道了可见光诱导的后期光氧化还原C–H酰胺化与N-未保护的吲哚和含色氨酸的肽，导致N的形成-（吲哚-2-基）酰胺衍生物。通过在室温下用绿色发光二极管照射，可以将含有吸电子基团的N-未保护的吲哚和芳氧基酰胺直接偶联至曙红Y作为光催化剂。机理研究和密度泛函理论计算表明，这种转变可能通过吲哚从PS *到PS •–循环的C–H氧化功能化而进行。该协议为N-未保护的吲哚衍生物的后期修饰标记和肽-药物结合提供了一个新的工具包。
• P^III -Chelation-Assisted Indole C7-Arylation, Olefination, Methylation, and Acylation with Carboxylic Acids/Anhydrides by Rhodium Catalysis
  作者：Xiaodong Qiu、Panpan Wang、Dingyi Wang、Minyan Wang、Yu Yuan、Zhuangzhi Shi

  DOI：10.1002/anie.201813182

  日期：2019.1.28

  olefination, and methylation of indoles with carboxylic acids or anhydrides by C−H and C−C bond activation have been developed. Furthermore, C7‐acylation products can also be generated selectively at a lower reaction temperature in the developed system. The key to the high reactivity and regioselectivity of this transformation is the appropriate choice of an indole N‐PtBu2 chelation‐assisted group

  已开发出通过CH和C-C键活化铑催化的C7-选择性脱羰芳基化，吲哚与羧酸或酸酐的吲哚甲基化反应。此外，在开发的系统中，还可以在较低的反应温度下选择性生成C7酰化产物。这一转变的高反应性和区域选择性的关键是吲哚的适当选择Ñ -P吨卜2螯合辅助基团。该方法具有许多优点，包括易于接近和除去导向基团，使用便宜且可广泛获得的偶联剂，不需要外部配体或氧化剂，广泛的底物范围，高效率以及形成唯一的区域异构体。
• Indole derivatives as potent inhibitors of 5-lipoxygenase: Design, synthesis, biological evaluation, and molecular modeling
  作者：Mingfang Zheng、Mingyue Zheng、Deju Ye、Yangmei Deng、Shuifeng Qiu、Xiaomin Luo、Kaixian Chen、Hong Liu、Hualiang Jiang

  DOI：10.1016/j.bmcl.2007.02.038

  日期：2007.5

  A series of novel indole derivatives was designed, synthesized and evaluated by cell-based assays for their inhibitory activities against 5-LOX in rat peritoneal leukocytes. Most of them (30 out of 35) showed an inhibitory potency higher than the initial screening hit 1a (IC50 = 74 mu M). Selected compounds for concentration-response studies showed prominent inhibitory activities with IC50 values ranging from 0.74 mu M to 3.17 mu M. Four compounds (1m, 1s, 4a, and 6a) exhibited the most potent inhibitory activity compared to that of the reference drug (Zileuton), with IC50 values less than I mu M. Molecular modeling studies for compounds 1a, 3a, 4a, and 6a were also presented. The excellent in vitro activities of this class of compounds may possess potential for the treatment of LT-related diseases. (C) 2007 Published by Elsevier Ltd.