(2S)-2-[(2R,4Z)-1-hydroxy-2-methylhepta-4,6-dienyl]-3-methylcyclobutan-1-one

• 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: (2S)-2-[(2R,4Z)-1-hydroxy-2-methylhepta-4,6-dienyl]-3-methylcyclobutan-1-one
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.3
• InChiKey: RGHNNFHXJNXUCY-POYWMRFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

文献信息

• CYCLOSPORINE ANALOGUE MIXTURES AND THEIR USE AS IMMUNOMODULATING AGENTS
  申请人：Aurinia Pharmaceuticals Inc.

  公开号：US20140142277A1

  公开（公告）日：2014-05-22

  The invention is directed to isomeric mixtures of cyclosporine analogues that are structurally similar to cyclosporine A. The mixtures possess enhanced efficacy and reduced toxicity over the individual isomers and over naturally occurring and other presently known cyclosporines and cyclosporine derivatives. Embodiments of the present invention are directed toward cis and trans-isomers of cyclosporin A analogs referred to as ISA TX 247, and derivatives thereof. Mixtures of ISA TX 247 isomers exhibit a combination of enhanced potency and reduced toxicity over the naturally occurring and presently known cyclosporins. ISA TX 247 isomers and alkylated, arylated, and deuterated derivatives are synthesized by stereoselective pathways where the particular conditions of a reaction determine the degree of stereoselectivity. The ratio of isomers in a mixture may range from about 10 to 90 percent by weight of the (E)-isomer to about 90 to 10 percent by weight of the (Z)-isomer, based on the total weight of the mixture.

  本发明涉及类似于环孢霉素A结构的环孢霉素类似物的异构混合物。这些混合物具有比单个异构体和天然存在的其他目前已知的环孢霉素和环孢霉素衍生物具有更强的功效和更少的毒性。本发明的实施例涉及称为ISATX247的环孢霉素A类似物的顺式和反式异构体及其衍生物。ISATX247异构体的混合物展示了天然存在的和目前已知的环孢霉素的强效和降低毒性的组合作用。通过立体选择性途径合成ISATX247异构体和烷基化，芳基化和氘代衍生物，其中反应的特定条件决定了立体选择性的程度。混合物中异构体的比例可以在总混合物重量的基础上从(E)-异构体的约10％至90％的重量到(Z)-异构体的约90％至10％的重量范围内。