3-[2-cyanoethoxy-[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-(2,6,6-trimethylcyclohex-2-en-1-yl)oct-5-enoxy]phosphinothioyl]oxypropanenitrile | 1000613-28-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-[2-cyanoethoxy-[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-(2,6,6-trimethylcyclohex-2-en-1-yl)oct-5-enoxy]phosphinothioyl]oxypropanenitrile
• CAS: 1000613-28-4
• 化学式: C₃₁H₄₇N₂O₄PS
• 分子量: 574.765
• InChiKey: KQLMUPDWNRXJIO-NSKAYECMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[2-cyanoethoxy-[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-(2,6,6-trimethylcyclohex-2-en-1-yl)oct-5-enoxy]phosphinothioyl]oxypropanenitrile 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-(2,6,6-trimethylcyclohex-2-en-1-yl)oct-5-enoxy]-dihydroxy-sulfanylidene-lambda5-phosphane
  参考文献：
  名称：

  Protein Phosphatase Inhibitors Isolated from Spongia irregularis Collected in Papua New Guinea

  摘要：

  Irregularasulfate (1), a new nitrogen-containing sesterterpenoid, and the known sesterterpenoids hipposulfate C (2), halisulfate-7 (3), and igernellin (4), have been isolated from the marine sponge Spongia irregularis collected in Papua New Guinea. The structure of I was elucidated via analysis of its spectroscopic data. Sesterterpenoids 1, 2, and 3 are moderate inhibitors of the catalytic subunits of the mammalian Ser/Thr protein phosphatases calcineurin, PP-1, and PP-2A. The phosphate analogue of 3 and the thiophosphate analogue of 2 have been prepared from the corresponding natural products and evaluated for their ability to inhibit the phosphatase activity of calcineurin.

  DOI：

  10.1021/np0702887
• 作为产物：
  描述：

  在 sulfur 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 以9.5 mg的产率得到3-[2-cyanoethoxy-[(E)-2-[3-(furan-3-yl)propyl]-6-methyl-8-(2,6,6-trimethylcyclohex-2-en-1-yl)oct-5-enoxy]phosphinothioyl]oxypropanenitrile
  参考文献：
  名称：

  Protein Phosphatase Inhibitors Isolated from Spongia irregularis Collected in Papua New Guinea

  摘要：

  Irregularasulfate (1), a new nitrogen-containing sesterterpenoid, and the known sesterterpenoids hipposulfate C (2), halisulfate-7 (3), and igernellin (4), have been isolated from the marine sponge Spongia irregularis collected in Papua New Guinea. The structure of I was elucidated via analysis of its spectroscopic data. Sesterterpenoids 1, 2, and 3 are moderate inhibitors of the catalytic subunits of the mammalian Ser/Thr protein phosphatases calcineurin, PP-1, and PP-2A. The phosphate analogue of 3 and the thiophosphate analogue of 2 have been prepared from the corresponding natural products and evaluated for their ability to inhibit the phosphatase activity of calcineurin.

  DOI：

  10.1021/np0702887