2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl berbamine | 1392417-43-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl berbamine
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-9-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 1392417-43-4
• 化学式: C₅₁H₅₈N₂O₁₅
• 分子量: 939.026
• InChiKey: QLJRJCDCZGNOIC-YMKZICCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  68
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  盐酸小檗胺 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 碳酸氢钠 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以50%的产率得到2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl berbamine
  参考文献：
  名称：

  Synthesis of berbamine acetyl glycosides and evaluation of antitumor activity

  摘要：

  A series of berbamine glycosides was designed, synthesized and evaluated as a new class of antitumor agents. An efficient glycosylation route was developed for berbamide derivatives. The newly synthesized glycosides were evaluated for their cytotoxic activity in vitro against a human leukemia cell line K562, a human lung adenocarcinoma cell line A549 and mouse lymphocytic leukemia cells L1210. In contrast to berbamine most of its glycosides manifested potent cytotoxic activities. The acetyl glycosyl berbamine 5a, 5d caused distinct improvement against K562, A549 and L1210. It is suggested that the acetyl D-glucose residue has affinity to these cancer cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.042

文献信息

• Synthesis of berbamine acetyl glycosides and evaluation of antitumor activity
  作者：Yanli Cui、Minghan Xu、Jianwei Mao、Jingfeng Ouyang、Rongzhen Xu、Yongping Yu

  DOI：10.1016/j.ejmech.2012.04.042

  日期：2012.8

  A series of berbamine glycosides was designed, synthesized and evaluated as a new class of antitumor agents. An efficient glycosylation route was developed for berbamide derivatives. The newly synthesized glycosides were evaluated for their cytotoxic activity in vitro against a human leukemia cell line K562, a human lung adenocarcinoma cell line A549 and mouse lymphocytic leukemia cells L1210. In contrast to berbamine most of its glycosides manifested potent cytotoxic activities. The acetyl glycosyl berbamine 5a, 5d caused distinct improvement against K562, A549 and L1210. It is suggested that the acetyl D-glucose residue has affinity to these cancer cells. (C) 2012 Elsevier Masson SAS. All rights reserved.