12-(thiazol-4-yl)abieta-8,11,13-trien-18-amide

• 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: 12-(thiazol-4-yl)abieta-8,11,13-trien-18-amide
• 英文别名: (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-6-(1,3-thiazol-4-yl)-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxamide
• 化学式: C₂₃H₃₀N₂OS
• 分子量: 382.57
• InChiKey: UTLQFEYQFMZGOF-YMPZKCBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  脱氢松香酸 在 aluminum (III) chloride 、 potassium carbonate 、 potassium hydroxide 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 12-(thiazol-4-yl)abieta-8,11,13-trien-18-amide
  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

文献信息

• Discovery of 12-Thiazole Abietanes as Selective Inhibitors of the Human Metabolic Serine Hydrolase hABHD16A
  作者：Tiina J. Ahonen、Juha R. Savinainen、Jari Yli-Kauhaluoma、Eija Kalso、Jarmo T. Laitinen、Vânia M. Moreira

  DOI：10.1021/acsmedchemlett.8b00442

  日期：2018.12.13

  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.