3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane | 99281-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane
• 英文别名: 3-(3,4-bis-benzyloxy-phenyl)propylamine；3-(3,4-bis(benzyloxy)phenyl)-1-aminopropane；3,4-Bis(phenylmethoxy)benzenepropanamine；3-[3,4-bis(phenylmethoxy)phenyl]propan-1-amine
• CAS: 99281-96-6
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: VNERBFCFOYZBRE-UHFFFAOYSA-N

物化性质

• 沸点：
  505.1±50.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane 在 硼烷四氢呋喃络合物 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 77.0h， 生成 1-<(3,4,5-trimethoxyphenyl)methyl>-7,8-bis(benzyloxy)-2,3,4,5-tetrhydro-1H-2-benzazepine
  参考文献：
  名称：

  Synthesis and investigation of the .alpha.-adrenoceptor agonist and platelet antiaggregatory properties of 1,7,8-trisubstituted 2,3,4,5-tetrahydro-1H-2-benzazepine analogs of trimetoquinol

  摘要：

  The synthesis and biological evaluation of 7,8-dihydroxy (2) and 7,8-methylenedioxy (3) analogues of 1-[(3,4,5-trimethyoxyphenyl)methyl]-2,3,4,5-tetradhyo-1H-2-b enzazepine on beta-adrenoceptor systems and human platelets were undertaken and compared with trimetoquinol (TMQ, 1). Whereas 1 is a potent beta-adrenoceptor agonist in guinea pig atria and trachea (pD2 = 8.2), analogue 2 was marginally effective at relaxing guinea pig tracheal smooth muscle (pD2 = 4.4) and inactive as an agonist on guinea pig atria. Analogues 2 and 3 were inhibitors of phospholipase C (PLC; from Clostridium perfringens) induced and secondary wave of ADP-induced aggregation responses and inactive against low-dose thrombin-induced or stable endoperoxide (U46619) induced human platelet aggregation. Against ADP-induced serotonin secretion, 3 was 9-fold more active than analogue 2. Further, the rank order of TMQ isomers and 3 as inhibitors of PLC-induced platelet aggregation, serotonin secretion, and phosphatidylinositol degradation was identical (3 greater than (S)-(-)-1 greater than (R)-(+)-1). The results suggest that these compounds are blocking the action of PLC by interfering with phosphatidylinositol turnover in platelet membranes. The inhibition of ADP-induced responses in human platelets by analogues 2 and 3 also suggests a site of inhibition at a level of arachidonic acid release. Thus, ring expansion of 1 as in the benzazepine analogues 2 and 3 has allowed us to develop selective inhibitors of platelet function that lack significant beta-adrenoceptor activity.

  DOI：

  10.1021/jm00152a003
• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane
  参考文献：
  名称：

  New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers

  摘要：

  We report new examples of a series of losartan-hydrocaffeic hybrids that bear novel ester, amide and amine linkers. These compounds were made by linking hydrocaffeic acid to the side chain of losartan at the C-5 position of the imidazole ring through different strategies. Experiments performed in cultured cells demonstrate that these new hybrids retain the ability to block the angiotensin II effect and have increased antioxidant ability. Most of them reduced arterial pressure in rats better or as much as losartan. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.043

文献信息

• New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers
  作者：Gonzalo García、Isabel Serrano、Patricia Sánchez-Alonso、Manuel Rodríguez-Puyol、Ramón Alajarín、Mercedes Griera、Juan J. Vaquero、Diego Rodríguez-Puyol、Julio Álvarez-Builla、María L. Díez-Marqués

  DOI：10.1016/j.ejmech.2012.01.043

  日期：2012.4

  We report new examples of a series of losartan-hydrocaffeic hybrids that bear novel ester, amide and amine linkers. These compounds were made by linking hydrocaffeic acid to the side chain of losartan at the C-5 position of the imidazole ring through different strategies. Experiments performed in cultured cells demonstrate that these new hybrids retain the ability to block the angiotensin II effect and have increased antioxidant ability. Most of them reduced arterial pressure in rats better or as much as losartan. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and investigation of the .alpha.-adrenoceptor agonist and platelet antiaggregatory properties of 1,7,8-trisubstituted 2,3,4,5-tetrahydro-1H-2-benzazepine analogs of trimetoquinol
  作者：Michael T. Clark、Jane Chang、Stephen S. Navran、Huzoor Akbar、Asoke Mukhopadhyay、Hebatalla Amin、Dennis R. Feller、Duane D. Miller

  DOI：10.1021/jm00152a003

  日期：1986.2

  The synthesis and biological evaluation of 7,8-dihydroxy (2) and 7,8-methylenedioxy (3) analogues of 1-[(3,4,5-trimethyoxyphenyl)methyl]-2,3,4,5-tetradhyo-1H-2-b enzazepine on beta-adrenoceptor systems and human platelets were undertaken and compared with trimetoquinol (TMQ, 1). Whereas 1 is a potent beta-adrenoceptor agonist in guinea pig atria and trachea (pD2 = 8.2), analogue 2 was marginally effective at relaxing guinea pig tracheal smooth muscle (pD2 = 4.4) and inactive as an agonist on guinea pig atria. Analogues 2 and 3 were inhibitors of phospholipase C (PLC; from Clostridium perfringens) induced and secondary wave of ADP-induced aggregation responses and inactive against low-dose thrombin-induced or stable endoperoxide (U46619) induced human platelet aggregation. Against ADP-induced serotonin secretion, 3 was 9-fold more active than analogue 2. Further, the rank order of TMQ isomers and 3 as inhibitors of PLC-induced platelet aggregation, serotonin secretion, and phosphatidylinositol degradation was identical (3 greater than (S)-(-)-1 greater than (R)-(+)-1). The results suggest that these compounds are blocking the action of PLC by interfering with phosphatidylinositol turnover in platelet membranes. The inhibition of ADP-induced responses in human platelets by analogues 2 and 3 also suggests a site of inhibition at a level of arachidonic acid release. Thus, ring expansion of 1 as in the benzazepine analogues 2 and 3 has allowed us to develop selective inhibitors of platelet function that lack significant beta-adrenoceptor activity.