podoscyphic acid methyl ester | 1018813-97-2

• 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: podoscyphic acid methyl ester
• 英文别名: methyl (E)-4,5-dioxohexadec-2-enoate
• CAS: 1018813-97-2
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: HJNWQPBMEBYKAS-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  podoscyphic acid methyl ester 、 1-benzyl-2-(ethoxycarbonylmethylene)-2,3,4,5-tetrahydroimidazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以52%的产率得到1-benzyl-5-dodecanoyl-5-hydroxy-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridine-7,8-dicarboxylic acid 8-ethyl ester 7-methyl ester
  参考文献：
  名称：

  Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-α expression in T cells

  摘要：

  Novel hexahydroimidazo[1,2-a]pyridines prepared by the addition of ethyl (1-benzylimidazolidin-2-ylidene)acetate (2) to the fungal metabolite podoscyphic acid (1a) and esters of la have been evaluated for their ability to inhibit the inducible TNF-alpha promoter activity in T cells. The methyl ester 3b is the most potent, inhibiting the TNF-alpha driven reporter gene expression in Jurkat T cells with an IC50-value of 2.0 mu g/ml (3.6 mu M). In addition, compound 3b inhibited the inducible TNF-alpha production in the myelomonocytic U937 cells with an IC50-value of 4.6 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.074

文献信息

• Imidazo[1,2-a]pyridine derivatives as inhibitors of TNF-α expression in T cells
  作者：Jan Rether、Gerhard Erkel、Timm Anke、Johan Bajtner、Olov Sterner

  DOI：10.1016/j.bmc.2007.10.074

  日期：2008.2.1

  Novel hexahydroimidazo[1,2-a]pyridines prepared by the addition of ethyl (1-benzylimidazolidin-2-ylidene)acetate (2) to the fungal metabolite podoscyphic acid (1a) and esters of la have been evaluated for their ability to inhibit the inducible TNF-alpha promoter activity in T cells. The methyl ester 3b is the most potent, inhibiting the TNF-alpha driven reporter gene expression in Jurkat T cells with an IC50-value of 2.0 mu g/ml (3.6 mu M). In addition, compound 3b inhibited the inducible TNF-alpha production in the myelomonocytic U937 cells with an IC50-value of 4.6 mu M. (c) 2007 Elsevier Ltd. All rights reserved.