7-(methoxymethoxy)-1H-isochromen-4(3H)-one | 1234672-74-2

• 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: 7-(methoxymethoxy)-1H-isochromen-4(3H)-one
• 英文别名: 7-(methoxymethoxy)-1H-isochromen-4-one
• CAS: 1234672-74-2
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: DCUYRPUBPWXUKE-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰基甲酸甲酯 、 7-(methoxymethoxy)-1H-isochromen-4(3H)-one 在 lithium diisopropyl amide 、 六甲基磷酰三胺 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 0.5h， 以52%的产率得到methyl 7-(methoxymethoxy)-4-oxo-3,4-dihydro-1H-isochromene-3-carboxylate
  参考文献：
  名称：

  Analogues of (3R)-7-Hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity

  摘要：

  The synthesis of compounds 6, 7a,b, 8a,b, 9a,b, and 10a,b where the amino -NH- group of JDTic (3) was replaced with an aromatic =CH-, CH2, O, S, or SO group was accomplished and used to further characterize the SAR of the compound 3 class of kappa opioid receptor antagonists. All of the compounds showed subnanomolar to low nanomolar K-e values at the kappa opioid receptor. The most potent compound was 7a, where the amino -NH- group of 3 was replaced by a methylene (-CH2-) group. This compound had a K-e = 0.18 nM and was 37- and 248-fold selective for the kappa relative to the mu and delta opioid receptors, respectively. Similar to compound 3, compound 7a antagonized selective kappa agonist U50,488-induced diuresis after sc administration in rats. In contrast to 3, where kappa antagonist activity lasted for three weeks, compound 7a did not show any kappa antagonist activity after one week.

  DOI：

  10.1021/jm1004978
• 作为产物：
  描述：

  7-hydroxy-1H-isochromen-4(3H)-one 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到7-(methoxymethoxy)-1H-isochromen-4(3H)-one
  参考文献：
  名称：

  Analogues of (3R)-7-Hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity

  摘要：

  The synthesis of compounds 6, 7a,b, 8a,b, 9a,b, and 10a,b where the amino -NH- group of JDTic (3) was replaced with an aromatic =CH-, CH2, O, S, or SO group was accomplished and used to further characterize the SAR of the compound 3 class of kappa opioid receptor antagonists. All of the compounds showed subnanomolar to low nanomolar K-e values at the kappa opioid receptor. The most potent compound was 7a, where the amino -NH- group of 3 was replaced by a methylene (-CH2-) group. This compound had a K-e = 0.18 nM and was 37- and 248-fold selective for the kappa relative to the mu and delta opioid receptors, respectively. Similar to compound 3, compound 7a antagonized selective kappa agonist U50,488-induced diuresis after sc administration in rats. In contrast to 3, where kappa antagonist activity lasted for three weeks, compound 7a did not show any kappa antagonist activity after one week.

  DOI：

  10.1021/jm1004978

文献信息

• Analogues of (3<i>R</i>)-7-Hydroxy-<i>N</i>-[(1<i>S</i>)-1-{[(3<i>R</i>,4<i>R</i>)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in Vitro and in Vivo Opioid Receptor Antagonist Activity
  作者：Scott P. Runyon、Lawrence E. Brieaddy、S. Wayne Mascarella、James B. Thomas、Hernán A. Navarro、James L. Howard、Gerald T. Pollard、F. Ivy Carroll

  DOI：10.1021/jm1004978

  日期：2010.7.22

  The synthesis of compounds 6, 7a,b, 8a,b, 9a,b, and 10a,b where the amino -NH- group of JDTic (3) was replaced with an aromatic =CH-, CH2, O, S, or SO group was accomplished and used to further characterize the SAR of the compound 3 class of kappa opioid receptor antagonists. All of the compounds showed subnanomolar to low nanomolar K-e values at the kappa opioid receptor. The most potent compound was 7a, where the amino -NH- group of 3 was replaced by a methylene (-CH2-) group. This compound had a K-e = 0.18 nM and was 37- and 248-fold selective for the kappa relative to the mu and delta opioid receptors, respectively. Similar to compound 3, compound 7a antagonized selective kappa agonist U50,488-induced diuresis after sc administration in rats. In contrast to 3, where kappa antagonist activity lasted for three weeks, compound 7a did not show any kappa antagonist activity after one week.