(5Z,9α,11α,13E,15S)-11,18-bis(acetoxy)-9,15-dihydroxyprosta-5,13-dien-1-oic acid | 74728-09-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5Z,9α,11α,13E,15S)-11,18-bis(acetoxy)-9,15-dihydroxyprosta-5,13-dien-1-oic acid
• 英文别名: 18-acetoxy-PGF2alpha-11-acetate；(Z)-7-[(1R,2R,3R,5S)-3-acetyloxy-2-[(E,3S)-6-acetyloxy-3-hydroxyoct-1-enyl]-5-hydroxycyclopentyl]hept-5-enoic acid
• CAS: 74728-09-9
• 化学式: C₂₄H₃₈O₈
• 分子量: 454.561
• InChiKey: RPLPBOQMXRLFMI-WWHNEAPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5Z,9α,11α,13E,15S)-11,18-bis(acetoxy)-9,15-dihydroxyprosta-5,13-dien-1-oic acid 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Prostaglandin Derivatives: Nonaromatic Phosphodiesterase-4 Inhibitors from the Soft Coral Sarcophyton ehrenbergi

  摘要：

  Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed.

  DOI：

  10.1021/np500394d

文献信息

• New prostaglandin (PGF) derivatives from the soft coral
  作者：S. Carmely、Y. Kashman、Y. Loya、Y. Benayahu

  DOI：10.1016/s0040-4039(00)71531-0

  日期：1980.1