2-氯-1-(6-甲氧基-1H-吲哚-3-基)乙-1-酮 | 38693-09-3

• 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-氯-1-(6-甲氧基-1H-吲哚-3-基)乙-1-酮
• 英文名称: 2-chloro-1-(6-methoxy-1H-indol-3-yl)ethanone
• 英文别名: 6-methoxy-3-(α-chloroacetyl)indole；2-chloro-1-(6-methoxy-indol-3-yl)-ethanone；6-Methoxy-3-chloracetyl-indol
• CAS: 38693-09-3
• 化学式: C₁₁H₁₀ClNO₂
• mdl: MFCD03848047
• 分子量: 223.659
• InChiKey: KCKIWBIWXRTIEM-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  413.8±30.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)
• 溶解度：
  5.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-氯-1-(6-甲氧基-1H-吲哚-3-基)乙-1-酮 在 platinum(IV) oxide 氢气 、 potassium bromide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 79.0h， 生成
  参考文献：
  名称：

  Tozo, Fujii; Ohba, Masashi; Tachinami, Takeshi, Chemical and pharmaceutical bulletin, 1991, vol. 39, # 1, p. 75 - 78

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基吲哚 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 生成 2-氯-1-(6-甲氧基-1H-吲哚-3-基)乙-1-酮
  参考文献：
  名称：

  通过常见的N-吲哚基三乙基硼酸酯从游离（NH）吲哚中集体合成3-乙酰基吲哚，吲哚-3-羧酸酯，吲哚-3-亚磺酸和3-（甲基磺酰基）吲哚

  摘要：

  据报道，通过常见的N-吲哚基三乙基硼酸酯中间体，可以利用容易获得的亲电子试剂（如酰氯，氯甲酸酯，亚硫酰氯和甲基磺酰氯）对游离（NH）吲哚进行一般和直接的C3功能化。反应在温和条件下平稳进行，收率高达93％。在C2，C4，C5，C6和C7位置带有取代基的吲哚具有良好的耐受性。各种重要的3-acylindoles，吲哚-3-羧酸酯，吲哚-3-亚磺酸和3-（甲基磺酰基）吲哚的易于获得证明了该方法的高度相容性和实用性。

  DOI：

  10.1021/acs.orglett.6b01970

文献信息

• 4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole Acylamines as Νovel Antimicrobial Agents: Synthesis, In Silico and In Vitro Evaluation
  作者：Sergei Simakov、Victor Kartsev、Anthi Petrou、Ioannis Nicolaou、Athina Geronikaki、Marija Ivanov、Marina Kostic、Jasmina Glamočlija、Marina Soković、Despoina Talea、Ioannis S. Vizirianakis

  DOI：10.3390/ph14111096

  日期：——

  4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (−) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive

  本手稿涉及 29 种 4-（吲哚-3-基）噻唑-2-胺和 4-吲哚-3-基）噻唑酰胺的抗菌活性的合成、计算和实验评估。对革兰氏 (+) 和革兰氏 (-) 细菌的抗菌活性评估表明，吲哚衍生物的 MIC 范围为 0.06-1.88 mg/mL，而在 14 种甲基吲哚衍生物中，只有 6 种具有活性，MIC 为范围为 0.47–1.88 mg/mL。S. aureus似乎是最具抗性的菌株，而S. Typhimurium 是最敏感的。化合物5x是最有希望的，MIC 在 0.06–0.12 mg/mL 范围内，其次是5d和5m. 对耐药菌株，即MRSA这三种化合物的评价P. 铜绿假单胞菌和E. 大肠杆菌，表明，它们更有效的抗MRSA比氨苄青霉素。此外，与氨苄青霉素和链霉素相比，化合物5m和5x是生物膜形成的优良抑制剂，就化合物5d、5m和5x以加性方式与链霉素相互作用而言。一些化合物的抗真菌活性超过或
• Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Emilio Russo、Giovambattista De Sarro、Mariangela Chisari、Lucia Ciranna、Julio Alvarez-Builla、Ramon Alajarin、Maria Rosa Buemi、Alba Chimirri

  DOI：10.1016/j.bmc.2013.12.040

  日期：2014.2

  A three-step synthetic pathway has been employed to synthesize a small library of 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl)ethanone and 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl) ethane-1,2-dione derivatives that have been screened in [H-3]ifenprodil competition binding assay. Some compounds exhibited significant binding affinity at nanomolar concentration, the most active being ligand 35 (IC50 = 5.5 nM). Docking experiments suggested the main interactions between 35 and GluN2B-containing NMDA receptors. Notably, the compound 35 reduced NMDA-mediated excitatory post-synaptic currents recorded in mouse hippocampal slices indicating antagonistic effects (50 nM). Moreover, the compound 35 has shown antioxidant effects in a preliminary screening, thus suggesting that it might be considered prototype for future drug development of novel 'dual target' neuroprotective agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Characterization of 3-Substituted-1<i>H</i>-indoles as Ligands of GluN2B-Containing <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptors
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Maria Rosa Buemi、Emilio Russo、Giovambattista De Sarro、Lara Costa、Lucia Ciranna、Orazio Prezzavento、Emanuela Arena、Simone Ronsisvalle、Giuseppe Bruno、Alba Chimirri

  DOI：10.1021/jm2008002

  日期：2011.12.22

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.
• FUJII, TOZO;OHBA, MASASHI;TACHINAMI, TAKESHI;OHASHI, TAKAKO;KOCH, MICHEL;+, HETEROCYCLES, 29,(1989) N, C. 1037-1040
  作者：FUJII, TOZO、OHBA, MASASHI、TACHINAMI, TAKESHI、OHASHI, TAKAKO、KOCH, MICHEL、+

  DOI：——

  日期：——
• FUJII, TOZO;OHBA, MASASHI;TACHINAMI, TAKESHI;OHASHI, TAKAKO, CHEM. AND PHARM. BULL., 39,(1991) N, C. 75-78
  作者：FUJII, TOZO、OHBA, MASASHI、TACHINAMI, TAKESHI、OHASHI, TAKAKO

  DOI：——

  日期：——