1-(β-D-glucopyranosyl)-5-nitroindoline | 727651-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)-5-nitroindoline
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(5-nitro-2,3-dihydroindol-1-yl)oxane-3,4,5-triol
• CAS: 727651-31-2
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: VKJPKSBZMSWVCD-RKQHYHRCSA-N

物化性质

• 熔点：
  70-75 °C
• 沸点：
  627.5±55.0 °C(Predicted)
• 密度：
  1.614±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(β-D-glucopyranosyl)-5-nitroindoline 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-nitroindole
  参考文献：
  名称：

  Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

  摘要：

  in the course of structure-activity relationship studies, diversely substituted 1-(beta-(D)-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.004
• 作为产物：
  描述：

  5-硝基二氢吲哚 、 葡萄糖 以 乙醇 、 水 为溶剂， 反应 144.0h， 以80%的产率得到1-(β-D-glucopyranosyl)-5-nitroindoline
  参考文献：
  名称：

  Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

  摘要：

  in the course of structure-activity relationship studies, diversely substituted 1-(beta-(D)-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.004

文献信息

• Synthesis of glycosyl-isoindigo derivatives
  作者：Mathieu Sassatelli、Elias Saab、Fabrice Anizon、Michelle Prudhomme、Pascale Moreau

  DOI：10.1016/j.tetlet.2004.04.167

  日期：2004.6

  The synthesis 1-(beta-D-glucopyranosyl)-isoindigo from commercially available indoline is described. The synthetic pathway used allowed the substitution of the aromatic moiety by either electron donor or acceptor substituents. (C) 2004 Elsevier Ltd. All rights reserved.