des-A,B-22,23-dinor-8β-[(tert-butyldimethylsilyl)oxy]chol-16-en-22-ol | 502687-69-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: des-A,B-22,23-dinor-8β-[(tert-butyldimethylsilyl)oxy]chol-16-en-22-ol
• 英文别名: (2S)-2-[(3aR,4S,7aS)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-3,3a,4,5,6,7-hexahydroinden-1-yl]propan-1-ol
• CAS: 502687-69-6
• 化学式: C₁₉H₃₆O₂Si
• 分子量: 324.579
• InChiKey: JHVJWKVUOMBHMG-QSOKESPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  des-A,B-22,23-dinor-8β-[(tert-butyldimethylsilyl)oxy]chol-16-en-22-ol 在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 N,N-二异丙基乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， -78.0~65.0 ℃ 、101.33 kPa 条件下， 反应 95.0h， 生成 (1R,3aR,7aR)-1-[(2S,3R)-3-(methoxymethoxy)hex-5-en-2-yl]-7a-methylhexahydro-1H-inden-4-ol
  参考文献：
  名称：

  Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

  摘要：

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.

  DOI：

  10.1021/acs.orglett.5b03138
• 作为产物：
  描述：

  (3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione 在 2,6-二甲基吡啶 、 三氟化硼乙醚 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 des-A,B-22,23-dinor-8β-[(tert-butyldimethylsilyl)oxy]chol-16-en-22-ol
  参考文献：
  名称：

  Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

  摘要：

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.

  DOI：

  10.1021/acs.orglett.5b03138

文献信息

• Synthesis of Novel Hapten Derivatives of 1α,25-Dihydroxy-vitamin D₃ and Its 20-Epi Analogue¹
  作者：Lars K. A. Blæhr,*、Fredrik Björkling、Martin J. Calverley、Ernst Binderup、Mikael Begtrup

  DOI：10.1021/jo026061s

  日期：2003.2.1

  Hapten derivatives of 1alpha,25-dihydroxyvitamin D(3) and its 20-epimer were synthesized and conjugated to a carrier protein for raising polyclonal antibodies. The haptens were linked through spacers at C-16, thereby exposing both the A-ring and the side chain of the molecules, to maximize antibody specificity. The spacers were introduced via stereoselective hydroboration of 16-ene intermediates as

  合成了1alpha，25-dihydroxyvitamin D（3）的Hapten衍生物及其20个受体，并将其缀合到载体蛋白上以产生多克隆抗体。半抗原通过在C-16处的间隔基连接，从而暴露分子的A环和侧链，以最大化抗体特异性。间隔基是通过16烯中间体的立体选择性硼氢化引入的，这是关键步骤。在免疫测定中，针对天然激素的抗体相对于具有A环或侧链修饰的衍生物对该化合物具有选择性。然而，针对20个末端的抗体不能识别侧链中的修饰。
• Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities
  作者：Kenji Sugimoto、Hisanari Yajima、Yusuke Hayashi、Daishiro Minato、Sayuri Terasaki、Chihiro Tohda、Yuji Matsuya

  DOI：10.1021/acs.orglett.5b03138

  日期：2015.12.4

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.