13-acetyl-20-tritylneophorbol | 777859-79-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 13-acetyl-20-tritylneophorbol
• 英文别名: [(1R,2S,6R,10S,11R,13S,15S)-1,6-dihydroxy-4,12,12,15-tetramethyl-5,14-dioxo-8-(trityloxymethyl)-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
• CAS: 777859-79-7
• 化学式: C₄₁H₄₂O₇
• 分子量: 646.78
• InChiKey: ZRJRHINPULWISC-YZEHGXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  13-acetyl-20-tritylneophorbol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以88%的产率得到20-tritylphorbobutanone
  参考文献：
  名称：

  佛波-树脂毒素 (RTX) 杂种的合成和生物学评价

  摘要：

  制备了在环 C 上修饰的 Phorboid 20-homovanillates 以模拟超强效香草树脂毒素 (RTX) 的构成和构象，并在 AB 环系统上修饰以抑制萜类核心的促肿瘤潜力。发现了几个意想不到的反应，并扩展了此类香草配体的构效关系。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400122
• 作为产物：
  描述：

  phorbol 13-acetate 20-tritylether 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到13-acetyl-20-tritylneophorbol
  参考文献：
  名称：

  佛波-树脂毒素 (RTX) 杂种的合成和生物学评价

  摘要：

  制备了在环 C 上修饰的 Phorboid 20-homovanillates 以模拟超强效香草树脂毒素 (RTX) 的构成和构象，并在 AB 环系统上修饰以抑制萜类核心的促肿瘤潜力。发现了几个意想不到的反应，并扩展了此类香草配体的构效关系。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400122

文献信息

• Synthesis and Evaluation of Phorboid 20-Homovanillates:  Discovery of a Class of Ligands Binding to the Vanilloid (Capsaicin) Receptor with Different Degrees of Cooperativity
  作者：Giovanni Appendino、Giancarlo Cravotto、Giovanni Palmisano、Rita Annunziata、Arpad Szallasi

  DOI：10.1021/jm960063l

  日期：1996.1.1

  A number of phorboid 20-homovanillates were prepared by condensation of phorbol 12,13-diesters and 12-dehydrophorbol 13-esters with Mem-homovanillic acid followed by removal of the protecting group with SnCl4 in THF. These compounds were evaluated for their ability to inhibit [H-3]resiniferatoxin (RTX) binding to rat spinal cord membranes. Compounds bearing a lipophilic ester group on ring C were considerably active, but a surprising tolerance of the vanilloid receptor toward the location and the orientation of this ester group was disclosed. Unexpectedly, these ligands could also diminish, to a variable degree, the positive cooperativity which characterizes RTX binding to the vanilloid receptor. Phorbol 12-phenylacetate 13-acetate 20-homovanillate (PPAHV, 6a), a compound which abolished binding cooperativity, was further tested in a variety of in vivo assays used to characterize vanilloid-like activity. PPAHV showed only a marginal pungency and failed to induce a measurable hypothermia response at doses (up to 200 mg/kg) at which it effectively desensitized against neurogenic inflammation. These data suggest that the peculiar binding behavior of these ligands might be associated with a distinct spectrum of biological activity.