3,4-dihydro-6-hydroxy-5-nitro-2,2,7,8-tetramethyl-1(2H)-benzopyran

• 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: 3,4-dihydro-6-hydroxy-5-nitro-2,2,7,8-tetramethyl-1(2H)-benzopyran
• 英文别名: 6-hydroxy-5-nitro-2,2,7,8-tetramethylchroman；2,2,7,8-tetramethyl-5-nitrochroman-6-ol；2,2,7,8-tetramethyl-5-nitro-3,4-dihydrochromen-6-ol
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: QPFZLSGRCSWSLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 palladium on activated charcoal 高氯酸 、 甲烷磺酸 、 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 20.0~90.0 ℃ 、7.09 MPa 条件下， 反应 7.08h， 生成 3,4-dihydro-6-hydroxy-5-nitro-2,2,7,8-tetramethyl-1(2H)-benzopyran
  参考文献：
  名称：

  不同酚类底物与一氧化氮和过氧亚硝酸盐反应的研究

  摘要：

  研究了不同酚类底物与一氧化氮和过氧亚硝酸盐的反应性。通常，硝化作用是与过氧亚硝酸盐的主要反应，而与一氧化氮水溶液的反应则导致硝基和亚硝基衍生物的混合物（取决于苯酚）。亚硝化作用发生在相对于OH基具有自由对位的苯酚底物上，1-萘酚除外，后者提供了2-和4-亚硝基衍生物的1：1混合物。Chromans 7和8与过氧亚硝酸盐具有最高的反应活性，这表明它们可以作为这种有毒中间体的有效清除剂。在两种情况下，相应的5-硝基衍生物都是唯一检测到的反应产物。最后，苯并二氢吡喃8与一氧化氮反应以90％的收率得到对苯醌衍生物22a这一事实表明，这种抗氧化剂也有可能作为生物组织中特定的一氧化氮示踪剂使用。

  DOI：

  10.1016/s0040-4020(99)00877-7

文献信息

• Treatment of mitochondrial diseases
  申请人：Walkinshaw Gail

  公开号：US20050065099A1

  公开（公告）日：2005-03-24

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

  这项发明涉及治疗或改善线粒体疾病，如阿尔茨海默病、帕金森病、弗里德雷希共济失调症（FRDA）、小脑共济失调、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）、带有红色纤维的肌阵挛性癫痫（MERFF）、肌萎缩侧索硬化症（ALS）、运动神经元疾病、亨廷顿病、黄斑变性和癫痫等疾病的治疗方法，所述方法使用本文描述的Formula I或Formula II的类胡萝卜素衍生物。
• Vitamin E Chemistry. Nitration of Non-α-tocopherols:  Products and Mechanistic Considerations
  作者：Anjan Patel、Falk Liebner、Thomas Netscher、Kurt Mereiter、Thomas Rosenau

  DOI：10.1021/jo0706832

  日期：2007.8.1

  In contrast to the α-form permethylated at the aromatic ring, non-α-tocopherols possess free aromatic ring positions which enable them to act as potent scavengers of electrophiles in vivo and in vitro. In preparation of enzymatic studies involving peroxynitrite and other nitrating systems, the behavior of non-α-tocopherols under nitration conditions was studied. The nitration products of β-, γ-, and

  与在芳环上被甲基化的α-形式相反，非α-生育酚具有游离的芳环位置，这使它们能够在体内和体外充当亲电试剂的有效清除剂。在准备涉及过氧亚硝酸盐和其他硝化系统的酶研究时，研究了非α-生育酚在硝化条件下的行为。鉴定，全面分析表征了β-，γ-和δ-生育酚的硝化产物，并通过对截短的模型化合物进行X射线晶体结构分析来支持其结构。即使在更剧烈的硝化条件下，2-C下也不会发生立体化学腐蚀。重新检查了γ-生育酚和δ-生育酚的亚硝化，邻苯二酚单肟，仅在γ-生育酚的情况下，在升高的温度下才释放羟胺，以提供稳定的邻苯二酚。δ-生育酚的单硝化选择性地在位置5进行。该选择性可以通过应变诱导键定位（SIBL）到醌型硝化中间体的理论来解释。双硝化对第一个硝基基团的影响很小，因此在正常硝化条件下提供过量硝化物种的情况下，仅发现了双硝化产物。
• TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Ampere Life Sciences, Inc.

  公开号：US20130267538A1

  公开（公告）日：2013-10-10

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

  本发明涉及使用式I或式II所描述的色酮衍生物的治疗或改善线粒体疾病的方法，例如阿尔茨海默病、帕金森病、弗里德雷希共济失调症（FRDA）、小脑共济失调、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）、带红纤维的肌阵挛性癫痫（MERFF）、肌萎缩侧索硬化症（ALS）、运动神经元疾病、亨廷顿病、黄斑退化和癫痫。
• Tocotrienamines and tocopheramines: Reactions with radicals and metal ions
  作者：Francesco Galli、Francesco Mazzini、Luca Bamonti、Lars Gille、Stefan Böhmdorfer、Marta Piroddi、Thomas Netscher、Frank J. Kelly、Thomas Rosenau

  DOI：10.1016/j.bmc.2011.08.050

  日期：2011.11

  The antioxidant activity of vitamin E (VE) homologs alpha, gamma and delta-tocotrienamines (4b-6b), never studied before, and alpha, gamma and delta-tocopheramines (4a-7a) was investigated by means of different total antioxidant capacity (TAC) tests. In all the test model systems, compounds 4a-7a and 4b-6b showed similar or higher TAC values than the parental vitamin E forms and their physiological metabolites. alpha-Homologs of VE amines showed markedly higher activity than the VE congeners in the TEAC test, which is tailored for liposoluble antioxidants, while gamma-homologs of the amine analogs showed higher activity in the FRAP tests. Kinetics analysis of the reaction with DPPH center dot showed higher second order rate k for 4a than for alpha-tocopherol (1a). alpha-Tocopherolquinone 1f was the common main oxidation product for both 1a and alpha-tocopheramine (4a) exposed to ferric ions or DPPH center dot, and the implied oxidative deamination of 4a was accompanied by a nitration reaction of phenolic substrates that were added to the reaction medium. Possible mechanisms of these reactions were studied. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] TREATMENT OF MITOCHONDRIAL DISEASES<br/>[FR] TRAITEMENT DE MALADIES MITOCHONDRIALES
  申请人：GALILEO PHARMACEUTICALS INC

  公开号：WO2005032544A1

  公开（公告）日：2005-04-14

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

表征谱图