(2S,3aR,6R,7S,7aR)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diol | 1616483-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3aR,6R,7S,7aR)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS: 1616483-01-2
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: SYRMQIFRELVNIX-PJEQPVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,6R,7S,7aR)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diol 、 碘甲烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以89%的产率得到3,4-di-O-methyl-1, 2-O-[(S)-ethylidenyl]-d-xylopyranose
  参考文献：
  名称：

  Synthesis and identification of cytotoxic diphyllin glycosides as vacuolar H+-ATPase inhibitors

  摘要：

  The concise syntheses of two natural diphyllin glycosides Cleistanthin-A (CA), Cleistanthoside-A (CleA) and its derivative, Cleistanthoside-A tetraacetate (CleT), have been achieved. They were evaluated for their in vitro anti-proliferative activities against MCF-7, HeLa, HepG2, HCT-116, U251 cancer cell lines by MTT assay. Both of CA and CleT were anti-proliferative to these cancer cells at nanomolar concentrations. They have been shown to inhibit the activity of vacuolar H+-ATPase (V-ATPase) in HepG2 cells and neutralize the pH of lysosomes at nanomolar concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.002
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 sodium tetrahydroborate 、 sodium methylate 、 四丁基碘化铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 26.0h， 生成 (2S,3aR,6R,7S,7aR)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diol
  参考文献：
  名称：

  Synthesis and identification of cytotoxic diphyllin glycosides as vacuolar H+-ATPase inhibitors

  摘要：

  The concise syntheses of two natural diphyllin glycosides Cleistanthin-A (CA), Cleistanthoside-A (CleA) and its derivative, Cleistanthoside-A tetraacetate (CleT), have been achieved. They were evaluated for their in vitro anti-proliferative activities against MCF-7, HeLa, HepG2, HCT-116, U251 cancer cell lines by MTT assay. Both of CA and CleT were anti-proliferative to these cancer cells at nanomolar concentrations. They have been shown to inhibit the activity of vacuolar H+-ATPase (V-ATPase) in HepG2 cells and neutralize the pH of lysosomes at nanomolar concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.002