2-(1-adamantyl)acetic acid 4-nitrophenyl ester | 76538-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-(1-adamantyl)acetic acid 4-nitrophenyl ester
• 英文别名: p-nitrophenyl 1-adamantaneacetate；p-Nitro-phenyl 1-adamantaneacetate；(4-nitrophenyl) 2-(1-adamantyl)acetate
• CAS: 76538-48-2
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: KOCOFPYWEFKYDP-UHFFFAOYSA-N

物化性质

• 沸点：
  451.4±28.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-adamantyl)acetic acid 4-nitrophenyl ester 在 β-环糊精 sodium hydroxide 、 乙腈 作用下， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Catalysis of the Hydrolysis ofp-Nitrophenyl 1-Adamantaneacetate by Cyclodextrins

  摘要：

  β-和γ-环糊精加速了对硝基苯基 1-金刚烷乙酸酯的裂解，这与它们对立体类似底物--对硝基苯基 1-金刚烷羧酸酯--裂解的减速作用形成鲜明对比。这些底物中是否存在亚甲基完全决定了环糊精速率效应的方向。由于环糊精与这些底物的包合物结构不同，因此具有特异性，这明确表明环糊精是相当好的酶模型。

  DOI：

  10.1246/bcsj.53.3266
• 作为产物：
  描述：

  对硝基苯酚 、 1-金刚烷乙酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 2-(1-adamantyl)acetic acid 4-nitrophenyl ester
  参考文献：
  名称：

  Catalysis of the Hydrolysis ofp-Nitrophenyl 1-Adamantaneacetate by Cyclodextrins

  摘要：

  β-和γ-环糊精加速了对硝基苯基 1-金刚烷乙酸酯的裂解，这与它们对立体类似底物--对硝基苯基 1-金刚烷羧酸酯--裂解的减速作用形成鲜明对比。这些底物中是否存在亚甲基完全决定了环糊精速率效应的方向。由于环糊精与这些底物的包合物结构不同，因此具有特异性，这明确表明环糊精是相当好的酶模型。

  DOI：

  10.1246/bcsj.53.3266

文献信息

• Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors
  作者：Mark R. Burns、C. Lance Carlson、Scott M. Vanderwerf、Josh R. Ziemer、Reitha S. Weeks、Feng Cai、Heather K. Webb、Gerard F. Graminski

  DOI：10.1021/jm0101040

  日期：2001.10.1

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.
• Catalysis of the Hydrolysis of<i>p</i>-Nitrophenyl 1-Adamantaneacetate by Cyclodextrins
  作者：Makoto Komiyama、Shohei Inoue

  DOI：10.1246/bcsj.53.3266

  日期：1980.11

  The cleavage of p-nitrophenyl 1-adamantaneacetate was accelerated by β- and γ-cyclodextrins, which was in contrast with their deceleration of the cleavage of a sterically analogous substrate, p-nitrophenyl 1-adamantanecarboxylate. The presence and absence of a methylene group in these substrates absolutely governed the directions of the rate effects of the cyclodextrins. The specificity, explicitly showing that cyclodextrins are quite good models of enzymes, was attributed to the difference of the structures of the inclusion complexes of cyclodextrins with these substrates.

  β-和γ-环糊精加速了对硝基苯基 1-金刚烷乙酸酯的裂解，这与它们对立体类似底物--对硝基苯基 1-金刚烷羧酸酯--裂解的减速作用形成鲜明对比。这些底物中是否存在亚甲基完全决定了环糊精速率效应的方向。由于环糊精与这些底物的包合物结构不同，因此具有特异性，这明确表明环糊精是相当好的酶模型。