Ethyl 2-[(6-bromo-2,3-dimethoxyphenyl)methoxy]propanoate | 948311-27-1

• 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: Ethyl 2-[(6-bromo-2,3-dimethoxyphenyl)methoxy]propanoate
• CAS: 948311-27-1
• 化学式: C₁₄H₁₉BrO₅
• 分子量: 347.206
• InChiKey: NQAVYXOGCPQQHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[(6-bromo-2,3-dimethoxyphenyl)methoxy]propanoate 在 aluminum (III) chloride 、 正丁基锂 、 potassium carbonate 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 3.5h， 生成 7-methoxy-3-methyl-8-(oxiran-2-ylmethoxy)isochroman-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：

  6-bromo-2,3-dimethoxybenzaldehyde 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 2-[(6-bromo-2,3-dimethoxyphenyl)methoxy]propanoate
  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

• Total synthesis and antihypertensive activity of (±)7,8-dihydroxy-3-methyl-isochromanone-4
  作者：Jie Liu、Hao Ren、Jinyi Xu、Renren Bai、Qi Yan、Wenlong Huang、Xiaoming Wu、Jihua Fu、Qiujuan Wang、Qian Wu、Rong Fu

  DOI：10.1016/j.bmcl.2008.12.102

  日期：2009.3

  This letter describes the total synthesis, preliminary biological evaluation and mechanism studies of a novel and structurally unique isochromanone, (±)7,8-dihydroxy-3-methyl-isochromanone-4 (1), a nature product contained in banana (Musa sapientum L.) peel. The bioassay showed that compound 1 displays potent antihypertensive activity in renal hypertensive rats and further mechanism studies revealed

  此信介绍的全合成，一种新型的初步生物评价和机制的研究和结构独特的异色满酮，（±）7,8-二羟基-3-甲基-异色满-4-（1），一个自然产物含在香蕉（芭蕉L.）剥皮。生物测定表明，化合物1在肾性高血压大鼠中显示出有效的降压活性，进一步的机理研究表明，它是一种ACEI抑制剂。
• 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.