6-(tert-butyldimethylsilanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid | 716320-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(tert-butyldimethylsilanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid
• 英文别名: 6-tert-butyl(dimethyl)silyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid；6-[Tert-butyl(dimethyl)silyl]oxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid
• CAS: 716320-66-0
• 化学式: C₂₀H₃₂O₄Si
• 分子量: 364.557
• InChiKey: ALROOSBMPZJCHH-UHFFFAOYSA-N

物化性质

• 熔点：
  61.7-63.1 °C
• 沸点：
  466.6±45.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tert-butyldimethylsilanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid 在 sodium hydroxide 哌啶 、 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 N,N-二甲基甘氨酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.25h， 生成 曲格列酮
  参考文献：
  名称：

  Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

  摘要：

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.087
• 作为产物：
  描述：

  6-(t-butyl-dimethyl-silyloxy)-2,5,7,8-tetramethyl-chroman-2-carboxylic acid methyl ester 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以72%的产率得到6-(tert-butyldimethylsilanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of conjugates of lupane triterpenoids with chromane antioxidants and in vitro study of their influence on the production of nitrogen monoxide and on the arginase activity in activated macrophages

  摘要：

  通过酯键结合，获得了与α-生育酚合成类似物偶联的白桦三萜（白桦脂醇、白桦脂酮酸和白桦脂酸）衍生物，并在体外进行了测试。结果显示，尽管其细胞毒性较低，但其中一些能够抑制一氧化氮的生成，而不影响精氨酸酶的活性，这表明它们具有抗炎和免疫调节的特性。

  DOI：

  10.1007/s11172-010-0382-y

文献信息

• Losartan-Antioxidant Hybrids: Novel Molecules for the Prevention of Hypertension-Induced Cardiovascular Damage
  作者：Gonzalo García、Manuel Rodríguez-Puyol、Ramón Alajarín、Isabel Serrano、Patricia Sánchez-Alonso、Mercedes Griera、Juan J. Vaquero、Diego Rodríguez-Puyol、Julio Álvarez-Builla、María L. Díez-Marqués

  DOI：10.1021/jm9003957

  日期：2009.11.26

  We report the first examples of a new series of antioxidant-sartan hybrids (AO-sartans), which were made by adding an antioxidant fragment to the hydroxymethyl side chain of losartan. Experiments performed in cultured cells demonstrate that these new hybrids retain the ability to block the angiotensin II effect with increased antioxidant ability. In hypertensive rats, these compounds show properties that suggest they may be more useful than losartan for controlling hypertension and preventing hypertension-induced cardiovascular damage.
• Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium
  作者：Yun-Hua Fan、Han Chen、Amarnath Natarajan、Yuhong Guo、Fred Harbinski、Julia Iyasere、William Christ、Huseyin Aktas、Jose A. Halperin

  DOI：10.1016/j.bmcl.2004.02.087

  日期：2004.5

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of conjugates of lupane triterpenoids with chromane antioxidants and in vitro study of their influence on the production of nitrogen monoxide and on the arginase activity in activated macrophages
  作者：A. Yu. Spivak、R. R. Khalitova、Yu. P. Bel’skii、A. N. Ivanova、E. R. Shakurova、N. V. Bel’skaya、V. N. Odinokov、M. G. Danilets、A. A. Ligacheva

  DOI：10.1007/s11172-010-0382-y

  日期：2010.12

  Conjugates of lupane triterpenoids (betulin and betulonic and betulinic acids) with synthetic analogs of α-tocopherol were obtained via ester bond formation and tested in vitro. Showing low cytotoxicity, some of them suppress nitrogen monoxide production without affecting the activity of arginase, which suggests their antiinflammatory and immunomodulating properties.

  通过酯键结合，获得了与α-生育酚合成类似物偶联的白桦三萜（白桦脂醇、白桦脂酮酸和白桦脂酸）衍生物，并在体外进行了测试。结果显示，尽管其细胞毒性较低，但其中一些能够抑制一氧化氮的生成，而不影响精氨酸酶的活性，这表明它们具有抗炎和免疫调节的特性。