1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindole | 884496-42-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindole
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-bromoindol-1-yl)oxan-2-yl]methyl acetate
• CAS: 884496-42-8
• 化学式: C₂₂H₂₄BrNO₉
• 分子量: 526.338
• InChiKey: FFBRQSGQFYDEIB-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindole 在 chromium(VI) oxide 、 4 A molecular sieve 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 26.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoisoindigo
  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：

  1-乙酰-5-溴吲哚啉 在 吡啶 、 sodium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 90.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindole
  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

• Pharmacokinetic evaluation of medicinally important synthetic N,N′ diindolylmethane glucoside: Improved synthesis and metabolic stability
  作者：Asmita Magotra、Abhishek Gour、Deepak K. Sharma、Ashutosh K. Dash、Gurdarshan Singh、Debaraj Mukherjee、Utpal Nandi

  DOI：10.1016/j.bmcl.2019.02.010

  日期：2019.4

  An improved route for the synthesis of N,N'-diindolyl methane (DIM) glycosides has been developed by using Fe/Al pillared clay catalyst. In-silico pharmacokinetics followed by in-vitro studies like aqueous solubility, lipophilicity, P-glycoprotein (P-gp) dependent ATPase activity, permeability, plasma protein binding, RBC partitioning, metabolic stability in different liver microsomes and its in-vitro-in-vivo

  通过使用铁/铝柱撑粘土催化剂，已开发出一种改进的合成N，N'-二吲哚基甲烷（DIM）糖苷的途径。进行计算机体内药代动力学研究，然后进行体外研究，例如水溶性，亲脂性，P-糖蛋白（P-gp）依赖性ATPase活性，通透性，血浆蛋白结合，RBC分配，不同肝微粒体的代谢稳定性及其体外研究对最有效的衍生物NGD16进行了-vivo外推。发现该化合物在大鼠肝微粒体（RLM）和人肝微粒体（HLM）中具有低溶解度，最佳亲脂性，无P-gp抑制活性，中等通透性，高血浆蛋白结合，低RBC分配，可接受的代谢稳定性具有中等肝提取率。