(Z)-3(S),4(S),5(R)-trihydroxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-hydroxy-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid | 1231185-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3(S),4(S),5(R)-trihydroxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-hydroxy-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid
• 英文别名: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]oxane-2-carboxylic acid
• CAS: 1231185-02-6
• 化学式: C₂₄H₂₈O₁₂
• 分子量: 508.479
• InChiKey: GKZORGOEWQADFX-CXUJUTRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (Z)-3(S),4(S),5(R)-triacetoxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-(p-toluenesulfonyloxy)-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以62%的产率得到(Z)-3(S),4(S),5(R)-trihydroxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-hydroxy-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid
  参考文献：
  名称：

  Regio- and Stereospecific Synthesis of Mono-β-d-Glucuronic Acid Derivatives of Combretastatin A-1

  摘要：

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

  DOI：

  10.1021/np100108e

文献信息

• Regio- and Stereospecific Synthesis of Mono-β-<scp>d</scp>-Glucuronic Acid Derivatives of Combretastatin A-1
  作者：Rajendra P. Tanpure、Tracy E. Strecker、David J. Chaplin、Bronwyn G. Siim、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1021/np100108e

  日期：2010.6.25

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.