(E)-N'-(3-cyanobenzylidene)-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzohydrazide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-N'-(3-cyanobenzylidene)-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzohydrazide
• 英文别名: N-[(E)-(3-cyanophenyl)methylideneamino]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzamide
• 化学式: C₂₁H₂₁N₃O₇
• 分子量: 427.414
• InChiKey: XKZGDPRGQFZJTP-DMSZEUQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  165
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-N'-(3-cyanobenzylidene)-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzohydrazide 、 乙酸酐 反应 6.0h， 生成 2-(acetoxymethyl)-6-(4-(5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives

  摘要：

  A new series of glycosyl oxadiazoles compounds were synthesized and characterized through H-1 NMR, C-13 NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6c, 6d, 6i, 6j, 6k and 6l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 mu M) compared with the reference medicine Rosiglitazone (5.23 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.042
• 作为产物：
  描述：

  4-O-β-D-glucopyranosyloxybenzoic acid methyl ester 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 14.0h， 生成 (E)-N'-(3-cyanobenzylidene)-4-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzohydrazide
  参考文献：
  名称：

  Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives

  摘要：

  A new series of glycosyl oxadiazoles compounds were synthesized and characterized through H-1 NMR, C-13 NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6c, 6d, 6i, 6j, 6k and 6l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 mu M) compared with the reference medicine Rosiglitazone (5.23 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.042

文献信息

• Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives
  作者：Kui Du、Xianting Cao、Pengfei Zhang、Hui Zheng

  DOI：10.1016/j.bmcl.2014.09.042

  日期：2014.11

  A new series of glycosyl oxadiazoles compounds were synthesized and characterized through H-1 NMR, C-13 NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6c, 6d, 6i, 6j, 6k and 6l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 mu M) compared with the reference medicine Rosiglitazone (5.23 mu M). (C) 2014 Elsevier Ltd. All rights reserved.