ingenol-5,20-acetonide-3-(2-ethyl-butanoate) | 1383741-02-3

• 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: ingenol-5,20-acetonide-3-(2-ethyl-butanoate)
• 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] 2-ethylbutanoate
• CAS: 1383741-02-3
• 化学式: C₂₉H₄₂O₆
• 分子量: 486.649
• InChiKey: KCHQRLZCHZCAKX-OSKODHJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• 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-(2-ethyl-butanoate) 在 盐酸 作用下， 以 水 为溶剂， 生成 ingenol-3-(2-ethyl-butanoate)
  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

• [EN] INGENOL-3-ACYLATES I<br/>[FR] INGÉNOL-3-ACYLATES I
  申请人：LEO PHARMA AS

  公开号：WO2012085189A1

  公开（公告）日：2012-06-28

  The invention relates to compounds of general formula (I) wherein R is (C1-C7)alkyl, (C2-C7)alkenyl or (C2-C7)alkynyl; wherein R is substituted with R1; and pharmaceutically acceptable salts, hydrates, or solvates thereof, for use -alone or in combination with one or more other pharmaceutically active compounds- in therapy, for preventing, treating or ameliorating diseases or conditions responsive to stimulation of neutrophil oxidative burst, responsive to stimulation of keratinocyte IL-8 release or responsive to induction of necrosis.

  本发明涉及一般式(I)的化合物，其中R为(C1-C7)烷基，(C2-C7)烯基或(C2-C7)炔基；其中R被R1取代；以及其药学上可接受的盐、水合物或溶剂化物，用于治疗、预防、治疗或改善对中性粒细胞氧化爆发刺激、角质细胞IL-8释放刺激或坏死诱导反应敏感的疾病或病情，可以单独使用或与一个或多个其他药物活性化合物结合使用。
• US9388124B2
  申请人：——

  公开号：US9388124B2

  公开（公告）日：2016-07-12