1-(β-D-glucopyranosyl)-5-phenylindoline | 884496-34-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(β-D-glucopyranosyl)-5-phenylindoline
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(5-phenyl-2,3-dihydroindol-1-yl)oxane-3,4,5-triol
• CAS: 884496-34-8
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: VARSUNYHQMNPKB-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(β-D-glucopyranosyl)-5-phenylindoline 在 chromium(VI) oxide 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 37.0h， 生成 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-phenylindoline-2,3-dione
  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-溴二氢吲哚 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 46.0h， 生成 1-(β-D-glucopyranosyl)-5-phenylindoline
  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 and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives
  作者：M SASSATELLI、F BOUCHIKHI、S MESSAOUDI、F ANIZON、E DEBITON、C BARTHOMEUF、M PRUDHOMME、P MOREAU

  DOI：10.1016/j.ejmech.2005.10.004

  日期：2006.1

  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.