methyl 12-(2-phenylthiazol-4-yl)abieta-8,11,13-trien-18-oate

• 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: methyl 12-(2-phenylthiazol-4-yl)abieta-8,11,13-trien-18-oate
• 英文别名: methyl (1R,4aS,10aR)-1,4a-dimethyl-6-(2-phenyl-1,3-thiazol-4-yl)-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• 化学式: C₃₀H₃₅NO₂S
• 分子量: 473.679
• InChiKey: SKJSZOOKCDEIIT-KXTWMDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  脱氢松香酸 在 aluminum (III) chloride 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 methyl 12-(2-phenylthiazol-4-yl)abieta-8,11,13-trien-18-oate
  参考文献：
  名称：

  Discovery of 12-Thiazole Abietanes as Selective Inhibitors of the Human Metabolic Serine Hydrolase hABHD16A

  摘要：

  Screening of an in-house library of compounds identified 12-thiazole abietanes as a new class of reversible inhibitors of the human metabolic serine hydrolase. Further optimization of the first hit compound lead to the 2-methylthiazole derivative 18, with an IC50 value of 3.4 +/- 0.2 mu M and promising selectivity. ABHD16A has been highlighted as a new target for inflammation-mediated pain, although selective inhibitors of hABHD16A (human ABHD16A) have not yet been reported. Our study presents abietane-type diterpenoids as an attractive starting point for the design of selective ABHD16A inhibitors, which will contribute toward understanding the significance of hABHD16A inhibition in vivo.

  DOI：

  10.1021/acsmedchemlett.8b00442