ethyl-3,7-dimethyl-9-(1-pyryl)-2E,4E,6E,8E-nonatetranoate | 256647-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: ethyl-3,7-dimethyl-9-(1-pyryl)-2E,4E,6E,8E-nonatetranoate
• 英文别名: ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-(pyren-1-yl)nona-2,4,6,8-tetraenoate；ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-pyren-1-ylnona-2,4,6,8-tetraenoate
• CAS: 256647-44-6
• 化学式: C₂₉H₂₆O₂
• 分子量: 406.524
• InChiKey: CNJNDZSJMDOCHR-KLUXDTLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl-3,7-dimethyl-9-(1-pyryl)-2E,4E,6E,8E-nonatetranoate 在 二异丁基氢化铝 作用下， 生成 3,7-dimethyl-9-(1-pyryl)-2E,4E,6E,8E-nonatetraene-1-ol
  参考文献：
  名称：

  Studies on Pyry I retinal Analogues of Bacteriorhodopsin

  摘要：

  AbstractThe retinal analogues 3‐methyl‐5‐(l‐pyryl)‐2E,4E‐penta‐dienal (1) and 3,7‐dimethyl‐9‐(l‐pyryl)‐2E,4E,6E,8E‐non‐atetraenal (2), which contain the tetra aromatic pyryl system, have been synthesized and characterized in order to examine the effect of the extended ring system on the binding capabilities and the function of bacteriorhodopsin (bR). The two bR mutants, E194Q and E204Q, known to have distinct proton‐pumping patterns, were also examined so that the effect of the bulky ring system on the proton‐pumping mechanism could be studied. Both retin‐als formed pigments with all three bacterioopsins, and these pigments were found to have absorption maxima in the range 498–516 nm. All the analogue pigments showed activity as proton pumps. The pigment formed from wild‐type apoprotein bR with 1 (with the shortened polyene side chain) showed an M intermediate at 400 nm and exhibited fast proton release followed by proton uptake. Extending the polyene side chain to the length identical with retinal, analogue 2 with wild‐type apoprotein gave a pigment that shows M and O intermediates at 435 nm and 650 nm, respectively. This pigment shows both fast and slow proton release at pH 7, suggesting that the pKa of the proton release group (in the M‐state) is higher in this pigment compared to native bR. Hydrogen azide ions were found to accelerate the rise and decay of the O intermediate at neutral pH in pyryl 2 pigment. The pigments formed between 2 and E194Q and E204Q showed proton‐pumping behavior similar to pigments formed with the native retinal, suggesting that the size of the chromophore ring does not alter the protein conformation at these sites.

  DOI：

  10.1111/j.1751-1097.1999.tb08307.x
• 作为产物：
  描述：

  3-甲酰基-2-丁烯酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 ethyl-3,7-dimethyl-9-(1-pyryl)-2E,4E,6E,8E-nonatetranoate
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008

文献信息

• Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part
  作者：George E. Magoulas、Stavros E. Bariamis、Constantinos M. Athanassopoulos、Anastasios Haskopoulos、Petros G. Dedes、Marios G. Krokidis、Nikos K. Karamanos、Dimitris Kletsas、Dionissios Papaioannou、George Maroulis

  DOI：10.1016/j.ejmech.2010.12.008

  日期：2011.2

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Studies on Pyry I retinal Analogues of Bacteriorhodopsin
  作者：Joydip Das、Rosalie K. Crouch、Rajni Govindjee、Sergei Balashov、Thomas Ebrey

  DOI：10.1111/j.1751-1097.1999.tb08307.x

  日期：1999.12

  AbstractThe retinal analogues 3‐methyl‐5‐(l‐pyryl)‐2E,4E‐penta‐dienal (1) and 3,7‐dimethyl‐9‐(l‐pyryl)‐2E,4E,6E,8E‐non‐atetraenal (2), which contain the tetra aromatic pyryl system, have been synthesized and characterized in order to examine the effect of the extended ring system on the binding capabilities and the function of bacteriorhodopsin (bR). The two bR mutants, E194Q and E204Q, known to have distinct proton‐pumping patterns, were also examined so that the effect of the bulky ring system on the proton‐pumping mechanism could be studied. Both retin‐als formed pigments with all three bacterioopsins, and these pigments were found to have absorption maxima in the range 498–516 nm. All the analogue pigments showed activity as proton pumps. The pigment formed from wild‐type apoprotein bR with 1 (with the shortened polyene side chain) showed an M intermediate at 400 nm and exhibited fast proton release followed by proton uptake. Extending the polyene side chain to the length identical with retinal, analogue 2 with wild‐type apoprotein gave a pigment that shows M and O intermediates at 435 nm and 650 nm, respectively. This pigment shows both fast and slow proton release at pH 7, suggesting that the pKa of the proton release group (in the M‐state) is higher in this pigment compared to native bR. Hydrogen azide ions were found to accelerate the rise and decay of the O intermediate at neutral pH in pyryl 2 pigment. The pigments formed between 2 and E194Q and E204Q showed proton‐pumping behavior similar to pigments formed with the native retinal, suggesting that the size of the chromophore ring does not alter the protein conformation at these sites.