(2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran | 380912-53-8

• 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: (2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran
• 英文别名: (2S,4S)-2-(dimethoxymethyl)-2-methyl-6-nitro-3,4-dihydrochromen-4-ol
• CAS: 380912-53-8
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: ROJXUMCKSCWJTH-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (2S)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran
  参考文献：
  名称：

  A Novel Anti-Ischemic ATP-Sensitive Potassium Channel (K_ATP) Opener without Vasorelaxation:  N-(6-Aminobenzopyranyl)-N‘-benzyl-N‘ ‘-cyanoguanidine Analogue

  摘要：

  This paper describes the design, synthesis, and biological evaluation of a novel anti-ischemic compound, (2S,3S,4R)-N-(6-amino-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-benzopyranyl)-N'-benzyl-N " -cyanoguanidine (33), and the structure-activity relationships leading to the discovery of this compound. Compound 33 significantly reduced the myocardial infarct zone to area at risk (IZ/AAR) in the ischemic myocardium rat model with high cardioselectivity. Since the cardioprotective effect of compound 33 is reversed by ATP-sensitive potassium channel (K-ATP) blockers, its anti-ischemic effect appears to be at least mediated by K-ATP opening. In addition, compound 33 shows good protective activity on neuronal cells against oxidative stress, and therefore it is suggested that compound 33 may have therapeutic potential both in cardio- and in neuroprotection.

  DOI：

  10.1021/jm010183f
• 作为产物：
  描述：

  (2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到(2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran
  参考文献：
  名称：

  A Novel Anti-Ischemic ATP-Sensitive Potassium Channel (K_ATP) Opener without Vasorelaxation:  N-(6-Aminobenzopyranyl)-N‘-benzyl-N‘ ‘-cyanoguanidine Analogue

  摘要：

  This paper describes the design, synthesis, and biological evaluation of a novel anti-ischemic compound, (2S,3S,4R)-N-(6-amino-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-benzopyranyl)-N'-benzyl-N " -cyanoguanidine (33), and the structure-activity relationships leading to the discovery of this compound. Compound 33 significantly reduced the myocardial infarct zone to area at risk (IZ/AAR) in the ischemic myocardium rat model with high cardioselectivity. Since the cardioprotective effect of compound 33 is reversed by ATP-sensitive potassium channel (K-ATP) blockers, its anti-ischemic effect appears to be at least mediated by K-ATP opening. In addition, compound 33 shows good protective activity on neuronal cells against oxidative stress, and therefore it is suggested that compound 33 may have therapeutic potential both in cardio- and in neuroprotection.

  DOI：

  10.1021/jm010183f

文献信息

• J. Med. Chem. 2001, 44, 4207-4215
  作者：

  DOI：——

  日期：——
• A Novel Anti-Ischemic ATP-Sensitive Potassium Channel (<i>K</i>_ATP) Opener without Vasorelaxation:  <i>N</i>-(6-Aminobenzopyranyl)-<i>N‘</i>-benzyl-<i>N‘ ‘</i>-cyanoguanidine Analogue
  作者：Sung-eun Yoo、Kyu Yang Yi、Sunkyung Lee、Jeehee Suh、Nakjeong Kim、Byung Ho Lee、Ho Won Seo、Sun-Ok Kim、Dong-Ha Lee、Hong Lim、Hwa Sup Shin

  DOI：10.1021/jm010183f

  日期：2001.11.1

  This paper describes the design, synthesis, and biological evaluation of a novel anti-ischemic compound, (2S,3S,4R)-N-(6-amino-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-benzopyranyl)-N'-benzyl-N " -cyanoguanidine (33), and the structure-activity relationships leading to the discovery of this compound. Compound 33 significantly reduced the myocardial infarct zone to area at risk (IZ/AAR) in the ischemic myocardium rat model with high cardioselectivity. Since the cardioprotective effect of compound 33 is reversed by ATP-sensitive potassium channel (K-ATP) blockers, its anti-ischemic effect appears to be at least mediated by K-ATP opening. In addition, compound 33 shows good protective activity on neuronal cells against oxidative stress, and therefore it is suggested that compound 33 may have therapeutic potential both in cardio- and in neuroprotection.