ingenol-5,20-acetonide-3-(2-amino-6-methoxy-benzoate) | 1383427-52-8

• 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-amino-6-methoxy-benzoate)
• 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-amino-6-methoxybenzoate
• CAS: 1383427-52-8
• 化学式: C₃₁H₃₉NO₇
• 分子量: 537.653
• InChiKey: JOVRAPIXBHUAMX-CSUXSPINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ingenol-5,20-acetonide-3-(2-amino-6-methoxy-benzoate) 、 苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer

  摘要：

  Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKC delta activation. A correlation between structure, chemical stability and biological activity was found and compared to ingenol mebutate (ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKC delta for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKC delta. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.073
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯甲酸 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 ingenol-5,20-acetonide-3-(2-amino-6-methoxy-benzoate)
  参考文献：
  名称：

  Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer

  摘要：

  Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKC delta activation. A correlation between structure, chemical stability and biological activity was found and compared to ingenol mebutate (ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKC delta for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKC delta. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.073

文献信息

• [EN] 3-ACYL-INGENOLS II<br/>[FR] 3-ACYL-INGÉNOLS II
  申请人：LEO PHARMA AS

  公开号：WO2012083954A1

  公开（公告）日：2012-06-28

  The invention relates to compounds of general formula I, (I), wherein R is wherein R is aryl substituted by R3; or R is (C3-Ci3)-cycloalkyl, (C3-Ci3)- cycloalkenyl or (C7-Ci3)-cycloalkynyl optionally substituted by R4; 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.

  该发明涉及一般式I的化合物，其中R是芳基，被R3取代；或者R是(C3-C13)-环烷基，(C3-C13)-环烯基或(C7-C13)-环炔基，可选择性地被R4取代；以及其在治疗中的药用盐、水合物或溶剂化合物，可单独使用或与一个或多个其他药用活性化合物结合使用，用于预防、治疗或改善对中性粒细胞氧化爆发刺激敏感的疾病或症状，对角质细胞IL-8释放刺激敏感的疾病或症状，或对坏死诱导敏感的疾病或症状。
• US9656945B2
  申请人：——

  公开号：US9656945B2

  公开（公告）日：2017-05-23