(S)-4-((6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methoxy)benzonitrile | 1430559-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (S)-4-((6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methoxy)benzonitrile
• 英文别名: 4-[[(2S)-6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methoxy]benzonitrile
• CAS: 1430559-08-2
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: FWPBQHVHTOWPGY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-((6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methoxy)benzonitrile 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 反应 1.0h， 生成 4-[[(2S)-6-amino-2,3-dihydro-1,4-benzodioxin-2-yl]methoxy]benzonitrile
  参考文献：
  名称：

  Towards dual antithrombotic compounds – Balancing thrombin inhibitory and fibrinogen GPIIb/IIIa binding inhibitory activities of 2,3-dihydro-1,4-benzodioxine derivatives through regio- and stereoisomerism

  摘要：

  Enantiomers of 2,3-dihydro-1,4-benzodioxine derivatives possessing both thrombin and fibrinogen GPIIb/IIIa binding inhibitory activities were prepared from (R)- and (S)-glycidol as potential dual antithrombotic compounds. The influence of chirality and substitution pattern on thrombin inhibition and on inhibition of fibrinogen binding to GPIIb/IIIa was analyzed. Docking studies were used in an attempt to rationalize the results. The (S)-isomers of both 2,3-dihydro-1,4-benzodioxine regioisomers at positions 6 and 7 were found to be better thrombin inhibitors than the corresponding (R)-enantiomers, whereas we observed that stereochemistry does not display a consistent influence on fibrinogen GPIIb/IIIa binding inhibitory activity. Compound 11b, the (S)-isomer of the 6-substituted regioisomer, possessed the best balanced dual activity, with K-i(thrombin) = 1.67 +/- 0.27 mu M and IC50(GPIIb/IIIa) = 0.665 +/- 0.26 mu M, raising the hope that merging anticoagulant and platelet antiaggregatory activities in the same molecule could lead to successful multitarget antithrombotic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.002
• 作为产物：
  描述：

  (S)-(6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol 、 4-羟基苯甲腈 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 以50%的产率得到(S)-4-((6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methoxy)benzonitrile
  参考文献：
  名称：

  Towards dual antithrombotic compounds – Balancing thrombin inhibitory and fibrinogen GPIIb/IIIa binding inhibitory activities of 2,3-dihydro-1,4-benzodioxine derivatives through regio- and stereoisomerism

  摘要：

  Enantiomers of 2,3-dihydro-1,4-benzodioxine derivatives possessing both thrombin and fibrinogen GPIIb/IIIa binding inhibitory activities were prepared from (R)- and (S)-glycidol as potential dual antithrombotic compounds. The influence of chirality and substitution pattern on thrombin inhibition and on inhibition of fibrinogen binding to GPIIb/IIIa was analyzed. Docking studies were used in an attempt to rationalize the results. The (S)-isomers of both 2,3-dihydro-1,4-benzodioxine regioisomers at positions 6 and 7 were found to be better thrombin inhibitors than the corresponding (R)-enantiomers, whereas we observed that stereochemistry does not display a consistent influence on fibrinogen GPIIb/IIIa binding inhibitory activity. Compound 11b, the (S)-isomer of the 6-substituted regioisomer, possessed the best balanced dual activity, with K-i(thrombin) = 1.67 +/- 0.27 mu M and IC50(GPIIb/IIIa) = 0.665 +/- 0.26 mu M, raising the hope that merging anticoagulant and platelet antiaggregatory activities in the same molecule could lead to successful multitarget antithrombotic agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.002