| 346589-29-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• CAS: 346589-29-5
• 化学式: C₂₉H₄₉O₈P
• 分子量: 556.677
• InChiKey: VLYAEWHBYBMXMQ-BYXHPCSDSA-N

反应信息

• 作为反应物：
  描述：

  在 sodium tetrahydroborate 、 重铬酸吡啶 、 Celite 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp.: revision of the structures of haplosamates A and B

  摘要：

  Two inhibitors of membrane-type matrix metalloproteinase (MT1-MMP) were isolated from a marine sponge Cribrochalinasp. Their structures were elucidated as unusual phosphorylated sterol sulfates by spectroscopic and chemical methods. One of the sterol sulfates was found to be identical to haplosamate A, whose structure was previously proposed to be a steroidal sulfamate ester, which led to structure revisions of both haplosamates A and B. The absolute stereochemistry of haplosamate A was determined by chemical transformation and the modified Mosher's method. The sterol sulfates inhibited MT1-MMP with IC50 values of 150 and 160 mug/mL, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00259-9
• 作为产物：
  描述：

  haplosamate A 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 苯甲酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  Isolation and structure elucidation of two phosphorylated sterol sulfates, MT1-MMP inhibitors from a marine sponge Cribrochalina sp.: revision of the structures of haplosamates A and B

  摘要：

  Two inhibitors of membrane-type matrix metalloproteinase (MT1-MMP) were isolated from a marine sponge Cribrochalinasp. Their structures were elucidated as unusual phosphorylated sterol sulfates by spectroscopic and chemical methods. One of the sterol sulfates was found to be identical to haplosamate A, whose structure was previously proposed to be a steroidal sulfamate ester, which led to structure revisions of both haplosamates A and B. The absolute stereochemistry of haplosamate A was determined by chemical transformation and the modified Mosher's method. The sterol sulfates inhibited MT1-MMP with IC50 values of 150 and 160 mug/mL, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00259-9