2H-吡咯并[2,3-b]吡啶-2-酮,1,3-二氢-5-碘- | 1160112-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 2H-吡咯并[2,3-b]吡啶-2-酮,1,3-二氢-5-碘-
• 中文别名: 1,3-二氢-5-碘代-2H-吡咯并[2,3-b]吡啶-2-酮
• 英文名称: 5-iodo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one
• 英文别名: 5-iodo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one
• CAS: 1160112-78-6
• 化学式: C₇H₅IN₂O
• 分子量: 260.034
• InChiKey: ALGOIAHLVWYPHU-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  303.6±52.0 °C(Predicted)
• 密度：
  2.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline-2,3-dione 、 2H-吡咯并[2,3-b]吡啶-2-酮,1,3-二氢-5-碘- 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到7'-aza-5'-iodo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo
  参考文献：
  名称：

  Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7′-azaisoindigo derivatives substituted by Sonogashira cross-coupling

  摘要：

  In the course of structure-activity relationship studies we were interested in the synthesis of isoindigo and 7'-azaisoindigo derivatives substituted at the N-1 position by a 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl), at the 5'-position by various chains introduced by Sonogashira cross-coupling and substituted or not at the 5-position by a bromine atom. To get an insight into the substitution pattern required for the best biological potencies, their kinase inhibitory potencies and their in vitro anti-proliferative activities were evaluated. The derivatives were tested toward four protein kinases (CDK5/p25, GSK3, CK1, Dyrk1A) and their in vitro anti proliferative activity was tested against two human myeloid leukaemia cell lines (K562 and HL60). (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.027
• 作为产物：
  描述：

  5-溴-7-氮杂氧化吲哚 在 copper(l) iodide 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以62%的产率得到2H-吡咯并[2,3-b]吡啶-2-酮,1,3-二氢-5-碘-
  参考文献：
  名称：

  Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7′-azaisoindigo derivatives substituted by Sonogashira cross-coupling

  摘要：

  In the course of structure-activity relationship studies we were interested in the synthesis of isoindigo and 7'-azaisoindigo derivatives substituted at the N-1 position by a 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl), at the 5'-position by various chains introduced by Sonogashira cross-coupling and substituted or not at the 5-position by a bromine atom. To get an insight into the substitution pattern required for the best biological potencies, their kinase inhibitory potencies and their in vitro anti-proliferative activities were evaluated. The derivatives were tested toward four protein kinases (CDK5/p25, GSK3, CK1, Dyrk1A) and their in vitro anti proliferative activity was tested against two human myeloid leukaemia cell lines (K562 and HL60). (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.027

文献信息

• AZABENZIMIDAZOLES AND THEIR USE AS AMPA RECEPTOR MODULATORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP3288940B9

  公开（公告）日：2021-07-21
• Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7′-azaisoindigo derivatives substituted by Sonogashira cross-coupling
  作者：Fadoua Bouchikhi、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.ejmech.2009.01.027

  日期：2009.6

  In the course of structure-activity relationship studies we were interested in the synthesis of isoindigo and 7'-azaisoindigo derivatives substituted at the N-1 position by a 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl), at the 5'-position by various chains introduced by Sonogashira cross-coupling and substituted or not at the 5-position by a bromine atom. To get an insight into the substitution pattern required for the best biological potencies, their kinase inhibitory potencies and their in vitro anti-proliferative activities were evaluated. The derivatives were tested toward four protein kinases (CDK5/p25, GSK3, CK1, Dyrk1A) and their in vitro anti proliferative activity was tested against two human myeloid leukaemia cell lines (K562 and HL60). (C) 2009 Elsevier Masson SAS. All rights reserved.