6-hydroxy-7-methoxy-3-methylisochroman-4-one | 1411987-09-1

• 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: 6-hydroxy-7-methoxy-3-methylisochroman-4-one
• 英文别名: 6-hydroxy-7-methoxy-3-methyl-1H-isochromen-4-one
• CAS: 1411987-09-1
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: LEZYOZBPNJVPPY-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：

  6-hydroxy-7-methoxy-3-methylisochroman-4-one 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.5h， 生成 6-(2-hydroxy-3-(methylamino)propoxy)-7-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 6-hydroxy-7-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

文献信息

• Identification of a Hydrogen-Sulfide-Releasing Isochroman-4-One Hybrid as a Cardioprotective Candidate for the Treatment of Cardiac Hypertrophy
  作者：Yu Wang、Yuechen Liu、Hongyu Wu、Shengtao Xu、Fenfen Ma

  DOI：10.3390/molecules27134114

  日期：——

  Cardiac pathological hypertrophy is associated with undesirable epigenetic changes and causes maladaptive cardiac remodeling and heart failure, leading to high mortality rates. Specific drugs for the treatment of cardiac hypertrophy are still in urgent need. In the present study, a hydrogen-sulfide-releasing hybrid 13-E was designed and synthesized by appending p-hydroxythiobenzamide (TBZ), an H2S-releasing donor, to an analog of our previously discovered cardioprotective natural product XJP, 7,8-dihydroxy-3-methyl-isochromanone-4. This hybrid 13-E exhibited excellent H2S-generating ability and low cellular toxicity. The 13-E protected against cardiomyocyte hypertrophy In Vitro and reduced the induction of Anp and Bnp. More importantly, 13-E could reduce TAC-induced cardiac hypertrophy In Vivo, alleviate cardiac interstitial fibrosis and restore cardiac function. Unbiased transcriptomic analysis showed that 13-E regulated the AMPK signaling pathway and influenced fatty acid metabolic processes, which may be attributed to its cardioprotective activities.

  心肌病理性肥厚与不良的表观遗传学变化有关，会引起不良的心脏重塑和心力衰竭，导致高死亡率。治疗心肌肥厚的特效药物仍亟待开发。在本研究中，通过将对羟基硫代苯甲酰胺（TBZ）（一种 H2S 释放供体）添加到我们之前发现的具有心脏保护作用的天然产物 XJP 的类似物 7,8-二羟基-3-甲基异色满酮-4 中，设计并合成了一种硫化氢释放杂交 13-E。这种杂交 13-E 具有出色的 H2S 生成能力和较低的细胞毒性。13-E 对体外心肌细胞肥大有保护作用，并能减少 Anp 和 Bnp 的诱导。更重要的是，13-E 能减轻 TAC 诱导的体内心脏肥大，减轻心脏间质纤维化并恢复心脏功能。无偏见的转录组分析表明，13-E 可调节 AMPK 信号通路并影响脂肪酸代谢过程，这可能是其具有心脏保护活性的原因。
• 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.