(2S,3R,4R)-3,4-dihydro-2-dimethoxymethyl-3,4-epoxy-2-methyl-6-nitro-2H-1-benzopyran | 380912-56-1

• 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: (2S,3R,4R)-3,4-dihydro-2-dimethoxymethyl-3,4-epoxy-2-methyl-6-nitro-2H-1-benzopyran
• 英文别名: (2S,3R,4R)-6-nitro-3,4-dihydro-3,4-epoxy-2-dimethoxymethyl-2-methyl-2H-1-benzopyran；(2S,3R,4R)-6-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran；(1aR,2S,7bR)-2-(dimethoxymethyl)-2-methyl-6-nitro-1a,7b-dihydrooxireno[2,3-c]chromene
• CAS: 380912-56-1
• 化学式: C₁₃H₁₅NO₆
• 分子量: 281.265
• InChiKey: IUCVZCYPEDRIRJ-WZRBSPASSA-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：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-3,4-dihydro-2-dimethoxymethyl-3,4-epoxy-2-methyl-6-nitro-2H-1-benzopyran 在 ammonium hydroxide 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 phenyl N-cyano-N'-[(2S,3R,4S)-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydrochromen-4-yl]carbamimidate
  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)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran 在 sodium hypochlorite 、 disodium hydrogenphosphate 、 (R,R)-mangane(III)-salen 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4R)-3,4-dihydro-2-dimethoxymethyl-3,4-epoxy-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

• Cardioselective anti-ischemic ATP-sensitive potassium channel (KATP) openers: benzopyranyl indoline and indole analogues
  作者：Sunkyung Lee、Kyu Yang Yi、Soo-Kyung Kim、Jeehee Suh、Nak Jeong Kim、Sung-eun Yoo、Byung Ho Lee、Ho Won Seo、Sun-Ok Kim、Hong Lim

  DOI：10.1016/s0223-5234(03)00063-1

  日期：2003.5

  This paper describes the design, syntheses, and biological evaluations of novel ATP-sensitive potassium channel (K(ATP)) openers, benzopyranyl indoline and indole derivatives. Among those, two enantiomers of indoline-2-carboxylic ethyl esters (14, 18) showed the best cardioprotective activities both in vitro and in vivo, while their vasorelaxation potencies were very low (concentration for 50% inhibition

  本文介绍了新型ATP敏感钾通道（K（ATP））开环剂，苯并吡喃基吲哚和吲哚衍生物的设计，合成和生物学评估。其中，二氢吲哚-2-羧酸乙酯的两种对映体（14、18）在体外和体内均显示出最佳的心脏保护活性，而它们的血管舒张效力却非常低（50％抑制血管舒张的浓度> 30 microM）。14的心脏保护作用被选择性的线粒体K（ATP）阻滞剂5-羟基癸酸酯完全逆转，表明其通过线粒体K（ATP）的开放可证明的保护机制。此外，我们使用2D-NMR，X射线晶体学和分子模型进行了构象分析，以研究该系列化合物的构效关系。
• [EN] BENZOPYRAN DERIVATIVES SUBSTITUTED WITH A BENZIMIDAZOLE DERIVATIVE, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, THEIR PREPARATIONS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES DE BENZOPYRANE SUBSTITUE PAR UN DERIVE DE BENZIMIDAZOLE, LEURS SELS ACCEPTABLES SUR LE PLAN PHARMACEUTIQUE, LEURS PREPARATIONS ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：DONGBU HANNONG CHEMICAL CO LTD

  公开号：WO2004106330A1

  公开（公告）日：2004-12-09

  The present invention relates to benzopyran derivatives substituted with a benzimidazole derivative, or pharmaceutically acceptable salts thereof, a preparation method of the same and pharmarceutical compositions containing them. Benzopyran derivatives substituted with a benzimidazole derivative, represented in Formula (1), have the function of protecting heart from ischemia-reperfusion without side effect like vasodilation, so that a pharmaceutical composition containing benzopyran derivatives substituted with a benzimidazole derivative or pharmaceutically acceptable salts thereof of the present invention as an effective ingredient can be effectively used for the protection of tissues influenced by ischemia-reperfusion, for example, for the protection of heart, nervous cells, brain, retinal cells, storage organs, etc. and for the treatment of diseases caused by ischemia-reperfusion.

  本发明涉及一种取代苯并吡喃衍生物的苯并咪唑衍生物，或其药学上可接受的盐，以及其制备方法和含有它们的药物组合物。取代苯并吡喃衍生物的苯并咪唑衍生物，如公式（1）所示，具有保护心脏免受缺血再灌注的作用，没有血管扩张等副作用，因此，含有本发明的取代苯并吡喃衍生物的苯并咪唑衍生物或其药学上可接受的盐作为有效成分的药物组合物可以有效用于保护受缺血再灌注影响的组织，例如，用于保护心脏、神经细胞、大脑、视网膜细胞、储存器官等，并用于治疗由缺血再灌注引起的疾病。
• Benzopyran derivatives substituted with secondary amines including imidazole, their preparation and pharmaceutical compositions containing them
  申请人：Yi Yang Kyu

  公开号：US20050267188A1

  公开（公告）日：2005-12-01

  The present invention relates to benzopyran derivatives substituted with secondary amines including imidazole, their preparation, and pharmaceutical compositions containing them. The present invention is pharmacologically useful for the treatment of cancer, rheumatoid arthritis, and diabetic retinopathies through anti-angiogenic properties, and also pharmacologically useful in the protection of heart and neuronal cells against ischemia-reperfusion injury or preserving organs.

  本发明涉及用次生胺包括咪唑取代的苯并吡喃衍生物、它们的制备以及包含它们的药物组合物。本发明在药理学上对于通过抗血管生成的性质治疗癌症、类风湿性关节炎和糖尿病视网膜病变非常有用，同时在保护心脏和神经细胞免受缺血再灌注损伤或保护器官方面也具有药理学上的用途。
• Benzopyran derivatives substituted with secondary amines including tetrazole, method for the preparation thereof and pharmaceutical compositions containing them
  申请人：Lim Hong

  公开号：US20060035948A1

  公开（公告）日：2006-02-16

  The present invention relates to benzopyran derivatives substituted with secondary amines including tetrazole, method for preparing thereof and pharmaceutical compositions containing them. The compounds of the present invention can be used for protecting neuronal cells and brain damage; antioxidation; inhibiting NO generation; protecting heart; suppressing angiogenesis; protecting preserving organs such as kidney, heart and tissue, and protecting organs in major cardiovascular surgery.

  本发明涉及用二级胺包括四唑取代的苯并吡喃衍生物，其制备方法以及含有它们的制药组合物。本发明的化合物可用于保护神经细胞和脑损伤；抗氧化；抑制NO生成；保护心脏；抑制血管生成；保护肾脏、心脏和组织等器官，并保护心血管手术中的器官。
• Benzopyran derivatives substituted with a thioxobenzoxazole derivative, pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containingthem
  申请人：Hwang Sun Kyung

  公开号：US20070093481A1

  公开（公告）日：2007-04-26

  The present invention relates to benzopyran derivatives substituted with a thioxobenzoxazole derivative, or pharmaceutically acceptable salts thereof, processes for preparing the same and a pharmaceutical composition containing the above as an effective ingredient Benzopyran derivatives substituted with thioxobenzoxazole derivatives, represented in , have the function of protecting heart from ischemia-reperfusion both in vivo and in vitro, so that a pharmaceutical composition containing benzopyran derivatives substituted with thioxobenzoxoazole derivatives or pharmaceutically acceptable salts thereof of the present invention as an effective ingredient can be effectively used for the protection of tissues influenced by ischemia-reperfusion, for example, for the protection of heart, nervous cells, brain, retinal cells, storage organs, etc, and for the treatment of diseases caused by ischemia-reperfusion.

  本发明涉及一种取代有硫代苯并噁唑衍生物的苯并吡喃衍生物，或其药学上可接受的盐，以及制备它们的方法和包含上述物质作为有效成分的制药组合物。取代有硫代苯并噁唑衍生物的苯并吡喃衍生物，如<公式1>所示，具有在体内和体外保护心脏免受缺血再灌注损伤的功能，因此，本发明的取代有硫代苯并噁唑衍生物的苯并吡喃衍生物或其药学上可接受的盐作为有效成分的制药组合物可以有效用于保护受缺血再灌注影响的组织，例如心脏、神经细胞、大脑、视网膜细胞、储存器官等的保护，以及治疗由缺血再灌注引起的疾病。