6-(1,3-dioxan-2-yl)-2-formylnaphthalene | 163163-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(1,3-dioxan-2-yl)-2-formylnaphthalene
• 英文别名: 6-(1,3-dioxan-2-yl)-2-naphthaldehyde；6-(1,3-Dioxan-2-yl)naphthalene-2-carbaldehyde
• CAS: 163163-89-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: YTLQQJQEDWJJAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1,3-dioxan-2-yl)-2-formylnaphthalene 在 正丁基锂 、 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 、 三乙胺 作用下， 反应 5.08h， 生成 (E)-7-[6-(1,3-dioxan-2-yl)naphthalen-2-yl]-7-pyridin-3-ylhept-6-enoic acid
  参考文献：
  名称：

  A Novel Approach to Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors Based on the Link of 1,3-Dioxane-Thromboxane Receptor Antagonists and -Thromboxane Synthase Inhibitors

  摘要：

  A new class of dual-acting racemic thromboxane receptor antagonist/thromboxane synthase inhibitors is reported, based on the novel approach of linking the known thromboxane synthase inhibitors (TXSI) dazoxiben (2) or isbogrel(11) (separately) to thromboxane receptor antagonists (TXRA) from the 1,3-dioxane series, such as ICI 192605 (10). Dual activity was observed in vitro with inhibition of human microsomal thromboxane synthase in the range IC50 = 0.01-1.0 mu M and receptor antagonist activity by inhibition of U46619-induced human platelet aggregation in the range pA(2) = 5.5-7.0. The in vitro results also showed that very large groups could be tolerated at the selected substitution positions of the TXRA and TXSI components. Oral activity was observed in ex vivo tests in both rats and dogs at a dose of 10 mg/kg. Thus, (E)-7-[4-[[4-[(2SR,4SR,5RS)-5-[(Z)-5-carboxypent-2-enyl]-4-(2-hydroxyphenyl)-1,3-dioxan-2-yl]benzyl]oxy]phenyl]-7-(3-pyridyl)hept-6-enoic acid (110) was both an antagonist (pA(2) = 6.7) and a synthase inhibitor (IC50 = 0.02 mu M). On oral dosing (10 mg/kg) to rats and dogs, 110 showed significant TXRA activity [concentration ratio >64 (rat, 3 h) and >59 +/- 11.3 (dog, 2 h) vs ex vivo U46619-induced platelet aggregation]. Inhibition of thromboxane synthase at the respective time points in these experiments was 81 +/- 4.4% (rat) and 69 +/- 4.8% (dog).

  DOI：

  10.1021/jm00010a005
• 作为产物：
  描述：

  2-Acetoxymethyl-6-hydroxymethylnaphthalene 在 草酰氯 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.75h， 生成 6-(1,3-dioxan-2-yl)-2-formylnaphthalene
  参考文献：
  名称：

  A Novel Approach to Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors Based on the Link of 1,3-Dioxane-Thromboxane Receptor Antagonists and -Thromboxane Synthase Inhibitors

  摘要：

  A new class of dual-acting racemic thromboxane receptor antagonist/thromboxane synthase inhibitors is reported, based on the novel approach of linking the known thromboxane synthase inhibitors (TXSI) dazoxiben (2) or isbogrel(11) (separately) to thromboxane receptor antagonists (TXRA) from the 1,3-dioxane series, such as ICI 192605 (10). Dual activity was observed in vitro with inhibition of human microsomal thromboxane synthase in the range IC50 = 0.01-1.0 mu M and receptor antagonist activity by inhibition of U46619-induced human platelet aggregation in the range pA(2) = 5.5-7.0. The in vitro results also showed that very large groups could be tolerated at the selected substitution positions of the TXRA and TXSI components. Oral activity was observed in ex vivo tests in both rats and dogs at a dose of 10 mg/kg. Thus, (E)-7-[4-[[4-[(2SR,4SR,5RS)-5-[(Z)-5-carboxypent-2-enyl]-4-(2-hydroxyphenyl)-1,3-dioxan-2-yl]benzyl]oxy]phenyl]-7-(3-pyridyl)hept-6-enoic acid (110) was both an antagonist (pA(2) = 6.7) and a synthase inhibitor (IC50 = 0.02 mu M). On oral dosing (10 mg/kg) to rats and dogs, 110 showed significant TXRA activity [concentration ratio >64 (rat, 3 h) and >59 +/- 11.3 (dog, 2 h) vs ex vivo U46619-induced platelet aggregation]. Inhibition of thromboxane synthase at the respective time points in these experiments was 81 +/- 4.4% (rat) and 69 +/- 4.8% (dog).

  DOI：

  10.1021/jm00010a005

文献信息

• Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection
  作者：Anton Granzhan、Marie-Paule Teulade-Fichou

  DOI：10.1016/j.tet.2008.12.035

  日期：2009.2

  Three bibrachial cyclobisintercaland-type macrocycles with a 2,6-naphthylene scaffold and pyrene, ferrocene, or primary amino groups in side chains were synthesized by a [2+2]-cyclocondensation of functionalized diethylenetriamine derivatives with naphthalene-2,6-dialdehyde, whereas their monobrachial counterparts were prepared by a [1+1]-cyclocondensation of polyamines with a corresponding dialdehyde

  通过功能化的二亚乙基三胺衍生物与萘-2,6-二醛的[2 + 2]-环缩合反应，合成了三个带有2,6-萘骨架和侧链上的pyr，二茂铁或伯氨基的双臂环双中间型大环化合物。而它们的单臂对应物是通过多胺与相应的二醛结构单元的[1 + 1]-环缩合制备的。fluorescence官能化的大环化合物能够在水介质中结合邻苯二甲酸和对苯二甲酸阴离子，这可以通过其荧光（准分子或单体）性质的变化进行监测。
• A Novel Approach to Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors Based on the Link of 1,3-Dioxane-Thromboxane Receptor Antagonists and -Thromboxane Synthase Inhibitors
  作者：Norman Ackerley、Andrew G. Brewster、George R. Brown、David S. Clarke、Alan J. Foubister、Stephen J. Griffin、Julian A. Hudson、Michael J. Smithers、Paul R. O. Whittamore

  DOI：10.1021/jm00010a005

  日期：1995.5

  A new class of dual-acting racemic thromboxane receptor antagonist/thromboxane synthase inhibitors is reported, based on the novel approach of linking the known thromboxane synthase inhibitors (TXSI) dazoxiben (2) or isbogrel(11) (separately) to thromboxane receptor antagonists (TXRA) from the 1,3-dioxane series, such as ICI 192605 (10). Dual activity was observed in vitro with inhibition of human microsomal thromboxane synthase in the range IC50 = 0.01-1.0 mu M and receptor antagonist activity by inhibition of U46619-induced human platelet aggregation in the range pA(2) = 5.5-7.0. The in vitro results also showed that very large groups could be tolerated at the selected substitution positions of the TXRA and TXSI components. Oral activity was observed in ex vivo tests in both rats and dogs at a dose of 10 mg/kg. Thus, (E)-7-[4-[[4-[(2SR,4SR,5RS)-5-[(Z)-5-carboxypent-2-enyl]-4-(2-hydroxyphenyl)-1,3-dioxan-2-yl]benzyl]oxy]phenyl]-7-(3-pyridyl)hept-6-enoic acid (110) was both an antagonist (pA(2) = 6.7) and a synthase inhibitor (IC50 = 0.02 mu M). On oral dosing (10 mg/kg) to rats and dogs, 110 showed significant TXRA activity [concentration ratio >64 (rat, 3 h) and >59 +/- 11.3 (dog, 2 h) vs ex vivo U46619-induced platelet aggregation]. Inhibition of thromboxane synthase at the respective time points in these experiments was 81 +/- 4.4% (rat) and 69 +/- 4.8% (dog).