(2S)-2-methyl-2-([1,3]-5,5-dimethyldioxan-2-yl)-6-nitro-2H-1-benzopyran | 335382-32-6

• 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)-2-methyl-2-([1,3]-5,5-dimethyldioxan-2-yl)-6-nitro-2H-1-benzopyran
• 英文别名: (2S)-2-(5,5-dimethyl-1,3-dioxan-2-yl)-2-methyl-6-nitrochromene
• CAS: 335382-32-6
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: LCORKMAQNVEIDS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-2-([1,3]-5,5-dimethyldioxan-2-yl)-6-nitro-2H-1-benzopyran 在 ammonium hydroxide 、 sodium hypochlorite 、 disodium hydrogenphosphate 、 (S,S)-Mn(III)-salen 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (2S,3S,4R)-2-methyl-2-([1,3]-5,5-dimethyldioxan-2-yl)-6-nitro-3-hydroxy-4-amino-3,4-dihydro-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-hydroxy-2-methyl-6-nitro-2H-1-benzopyran 在 对甲苯磺酸 、 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-methyl-2-([1,3]-5,5-dimethyldioxan-2-yl)-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

• Benzopyranyl guanidine derivatives, process for preparation thereof, and pharmaceutical compositions containing them
  申请人：Dongbu Hannong Chemical Co., Ltd.

  公开号：US06323238B1

  公开（公告）日：2001-11-27

  The present invention relates to novel benzopyranyl guanidine derivatives of the formula 1, process for preparation therof and pharmaceutical use of the benzopyranyl guanidine derivatives. The benzopyranyl guanidine derivatives of the present invention can be used for protecting heart, neuronal cell or brain damage, preserving organs, and also the benzopyranyl guanidine derivatives are pharmacologically useful for inhibiting NO generation, and for suppressing lipid peroxidation, angiogenesis or restenosis. Wherein R1, R2, R3, R4, R5, R6, n and * are each defined in specification.

  本发明涉及一种新型苯并吡喃基胍衍生物的公式1，其制备方法以及苯并吡喃基胍衍生物的药用。本发明的苯并吡喃基胍衍生物可用于保护心脏、神经细胞或大脑损伤，保护器官，并且苯并吡喃基胍衍生物在药理学上可用于抑制NO生成，抑制脂质过氧化，抑制血管生成或再狭窄。其中，R1、R2、R3、R4、R5、R6、n和*在说明书中各自有定义。
• 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.