ingenol-5,20-acetonide-3-(cyclobutanecarboxylate) | 1383427-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: ingenol-5,20-acetonide-3-(cyclobutanecarboxylate)
• 英文别名: [(1S,4S,5S,6R,13S,14R,16R,18R)-5-hydroxy-3,8,8,15,15,18-hexamethyl-19-oxo-7,9-dioxapentacyclo[11.5.1.01,5.06,11.014,16]nonadeca-2,11-dien-4-yl] cyclobutanecarboxylate
• CAS: 1383427-23-3
• 化学式: C₂₈H₃₈O₆
• 分子量: 470.606
• InChiKey: ZAGIHXYOZFVWTM-FYLSQRFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ingenol-5,20-acetonide-3-(cyclobutanecarboxylate) 在 盐酸 作用下， 以 水 为溶剂， 生成 ingenol-3-(cyclobutanecarboxylate)
  参考文献：
  名称：

  Syntheses, biological evaluation and SAR of ingenol mebutate analogues for treatment of actinic keratosis and non-melanoma skin cancer

  摘要：

  Ingenol mebutate is the active ingredient in Picato (R) a new drug for the treatment of actinic keratosis. A number of derivatives related to ingenol mebutate were prepared by chemical synthesis from ingenol with the purpose of investigating the SAR and potency in assays relating to pro-inflammatory effects (induction of PMN oxidative burst and keratinocyte cytokine release), the potential of cell death induction, as well as the chemical stability. By modifications of the ingenol scaffold several prerequisites for activity were identified. The chemical stability of the compounds could be linked to an acyl migration mechanism. We were able to find analogues of ingenol mebutate with comparable in vitro properties. Some key features for potent and more stable ingenol derivatives have been identified. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.038

文献信息

• US9656945B2
  申请人：——

  公开号：US9656945B2

  公开（公告）日：2017-05-23