2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone | 81633-43-4

• 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: 2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone
• 英文别名: 3-(Chloroacetyl)-5,6-dimethoxyindole
• CAS: 81633-43-4
• 化学式: C₁₂H₁₂ClNO₃
• 分子量: 253.685
• InChiKey: DNAWOYJKUAXVLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chloro-1-(5,6-dimethoxy-1H-indol-3-yl)ethanone 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 利舍匹林
  参考文献：
  名称：

  Sakai, Shin-ichiro; Saito, Naoki; Hirose, Naohiro, Heterocycles, 1982, vol. 17, p. 99 - 103

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二甲氧基吲哚 、 氯乙酰氯 以51%的产率得到
  参考文献：
  名称：

  FUJII, TOZO;OHBA, MASASHI;TACHINAMI, TAKESHI;MIYAJIMA, HISAE, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1200-1204

  摘要：

  DOI：

文献信息

• Quinolizidines. XXVII. Racemic and chiral syntheses of the Neisosperma and Ochrosia alkaloid ochropposinine.
  作者：Tozo FUJII、Masashi OHBA、Takeshi TACHINAMI、Hisae MIYAJIMA

  DOI：10.1248/cpb.38.1200

  日期：——

  The first total synthesis of ochropposinine (1), a Neisosperma and Ochrosia alkaloid, has been accomplished in the form of a racemic modification by means of an initial coupling of the lactim ether (±)-3 with 5 and succeeding steps proceeding through the intermediates (±)-7, (±)-8, (±)-9, (±)-10, and (±)-11. A parallel synthetic route starting with (+)-3 produced the chiral target molecule (-)-1 via the intermediates (+)-7, (+)-8, (+)-9, 10, and (-)-11. As a result, the absolute configuration of ochropposinine has been unequivocally established to be that represented by formula (-)-1.

  通过内脂醚 (±)-3 与 5 的初始偶联，以及通过中间体 (±)-7、(±)-8、(±)-9、(±)-10 和 (±)-11 进行的后续步骤，首次以外消旋体改性的形式完成了赭桐碱 (1) 的全合成。从 (+)-3 开始的平行合成路线通过中间体 (+)-7、(+)-8、(+)-9、10 和 (-)-11 生成手性目标分子 (-)-1。因此，赭泊苷的绝对构型被明确确定为式 (-)-1 所代表的构型。
• 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.
• Structure Determination of the Ochrosia Alkaloid Ochropposinine: Syntheses of (±)- and (-)-Ochropposinine
  作者：Tozo Fujii、Masashi Ohba、Yakeshi Tachinami、Hisae Miyajima、Michel Koch、Elisabeth Seguin

  DOI：10.3987/r-1986-05-1215

  日期：——
• Sakai, Shin-ichiro; Saito, Naoki; Hirose, Naohiro, Heterocycles, 1982, vol. 17, p. 99 - 103
  作者：Sakai, Shin-ichiro、Saito, Naoki、Hirose, Naohiro、Yamanaka, Etsuji

  DOI：——

  日期：——
• FUJII, TOZO;OHBA, MASASHI;TACHINAMI, TAKESHI;MIYAJIMA, HISAE, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1200-1204
  作者：FUJII, TOZO、OHBA, MASASHI、TACHINAMI, TAKESHI、MIYAJIMA, HISAE

  DOI：——

  日期：——