(6-methoxy-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-5-yl)-methanamine | 784143-55-1

• 物质功能分类: 有机原料 - 氨基化合物
• 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: (6-methoxy-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-5-yl)-methanamine
• 英文别名: (6-Methoxy-2,2,7,8-tetramethylchroman-5-yl)methanamine；(6-methoxy-2,2,7,8-tetramethyl-3,4-dihydrochromen-5-yl)methanamine
• CAS: 784143-55-1
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: NVEZILPGMGAYHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.0±42.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6-methoxy-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-5-yl)-methanamine 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 5-[1,2]Dithiolan-3-yl-pentanoic acid (6-hydroxy-2,2,7,8-tetramethyl-chroman-5-ylmethyl)-amide
  参考文献：
  名称：

  Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias

  摘要：

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.012
• 作为产物：
  描述：

  5-(azidomethyl)-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl methyl ether 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以82.3%的产率得到(6-methoxy-2,2,7,8-tetramethyl-3,4-dihydro-2H-chromen-5-yl)-methanamine
  参考文献：
  名称：

  Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias

  摘要：

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.012

文献信息

• Chroman/Catechol Hybrids:  Synthesis and Evaluation of Their Activity against Oxidative Stress Induced Cellular Damage
  作者：Maria Koufaki、Elissavet Theodorou、Dimitrios Galaris、Lambros Nousis、Efrosini S. Katsanou、Michael N. Alexis

  DOI：10.1021/jm0506120

  日期：2006.1.1

  chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells from H(2)O(2)-induced DNA damage was evaluated using single cell gel electrophoresis (comet assay), while the neuroprotective activity of the new compounds against oxidative

  合成了三类在邻苯二酚衍生物在2或5位取代的苯并二氢吡喃，并研究了它们对氧化应激诱导的细胞损伤的活性。具体来说，使用单细胞凝胶电泳（彗星试验）评估了新分子保护培养的细胞免受H（2）O（2）诱导的DNA损伤的能力，而新化合物针对氧化应激诱导的神经保护活性被编程使用谷氨酸-challanged海马HT22细胞研究了细胞死亡。大多数新化合物比槲皮素具有更强的神经保护作用。5-取代的苯并二氢吡喃类似物，例如咖啡酰胺12和16和二氢二苯乙烯类似物24，分别对Jurkat T细胞和HT22细胞中H（2）O（2）-和谷氨酸诱导的损伤最有效。
• Synthesis of a second generation chroman/catechol hybrids and evaluation of their activity in protecting neuronal cells from oxidative stress-induced cell death
  作者：Maria Koufaki、Elissavet Theodorou、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2010.04.042

  日期：2010.6.1

  A new generation of chroman/catechol hybrids bearing heterocyclic five-membered rings, such as 1,2, 4-oxadiazole 1,3,4-oxadiazole, 1,2,3-triazole, tetrazole and isoxazole, were designed and synthesized. The activity of the new derivatives against oxidative stress induced neuronal damage, was evaluated using glutamate-challenged hippocampal HT22 cells.Compound 3 in which a 3,4-dimethoxyphenyl moiety, is directly attached to the 1,2,4-oxadiazole ring was the most active among the 2-substituted chroman analogues, with EC50 = 254 +/- 65 nM. Concerning the 5-subtituted chroman analogues, isoxazole derivative 29 exhibited the strongest activity (EC50 = 245 +/- 38 nM). However, 29 was cytotoxic at concentrations higher than 1 mu M, while the triazole analogue 24 (EC50 = 801 +/- 229 nM), was non-toxic at all concentrations tested. (C) 2010 Elsevier Ltd. All rights reserved.
• Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids
  作者：Maria Koufaki、Christina Kiziridi、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2009.07.010

  日期：2009.9.1

  Novel 1,2-dithiolane/chroman hybrids bearing heterocyclic rings such as 1,2,4- and 1,3,4-oxadiazole, 1,2,3-triazole and tetrazole were designed and synthesized. The neuroprotective activity of the new analogues was tested against oxidative stress-induced cell death of glutamate-challenged HT22 hippocampal neurons. Our results show that bioisosteric replacement of amide group in 2-position of the chroman moiety, by 1,3,4- oxadiazole did not affect activity. However, analogue 5 bearing the 1,2,4- oxadiazole moiety showed improved neuroprotective activity. The presence of nitrogen heterocycles strongly influences the neuroprotective activity of 5-substituted chroman derivatives, depending on the nature of heterocycle. Replacement of the amide group of the first generation analogues by 1,2,4- oxadiazole or 1,2,3-triazole resulted in significant improvement of the activity against glutamate induced oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.