7-hydroxy-6-methoxy-3-methyl-1H-isochromen-4-one | 1411987-16-0

• 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-hydroxy-6-methoxy-3-methyl-1H-isochromen-4-one
• CAS: 1411987-16-0
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: XJUAOBWJQWBVMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-6-methoxy-3-methyl-1H-isochromen-4-one 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.5h， 生成 7-(2-hydroxy-3-(methylamino)propoxy)-6-methoxy-3-methylisochroman-4-one
  参考文献：
  名称：

  Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

  摘要：

  A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent beta(1)-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.044
• 作为产物：
  描述：

  2-溴-4,5-二甲氧基苄醇 在 aluminum (III) chloride 、 正丁基锂 、 sodium hydride 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-hydroxy-6-methoxy-3-methyl-1H-isochromen-4-one
  参考文献：
  名称：

  Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

  摘要：

  A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent beta(1)-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.044

文献信息

• Novel nitric oxide-releasing isochroman-4-one derivatives: Synthesis and evaluation of antihypertensive activity
  作者：Renren Bai、Xue Yang、Yao Zhu、Zhiwen Zhou、Weijia Xie、Hequan Yao、Jieyun Jiang、Jie Liu、Mingqin Shen、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmc.2012.09.043

  日期：2012.12

  By coupling nitric oxide (NO)-donor moieties with a natural antihypertensive product (+/-)-7,8-dihydroxy3-methyl-isochroman-4-one [(+/-)-XJPI and its analogue (+/-)-XJP-B, a series of novel NO-releasing isochroman-4-one derivatives were designed and synthesized. The NO-releasing assay indicated that compounds Ia, Id, IIIb and IIIe released the maximum amount of NO. The maximum reductions of blood pressure of Ia, IIIb and IIIe in SHRs were nearly 40%, which was obviously superior to that of the lead compounds and comparable to that of reference drug captopril. These results suggested that NO-donor/natural product hybrids may provide a promising approach for the discovery of novel antihypertensive agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates
  作者：Renren Bai、Xiaojing Huang、Xue Yang、Wen Hong、Yiqun Tang、Hequan Yao、Jieyun Jiang、Jie Liu、Mingqin Shen、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmc.2013.02.044

  日期：2013.5

  A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent beta(1)-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.