2-ethynyl-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran | 1333118-52-7

• 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: 2-ethynyl-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran
• 英文别名: 2-Ethynyl-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydrochromene
• CAS: 1333118-52-7
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: TVZJFSXMAVGQOK-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethynyl-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran 在 copper(ll) sulfate pentahydrate 、 三氟二甲基硫醚络合物 、 chloroamine-T 、 铜 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3,4-dihydro-2,5,7,8-tetramethyl-2-(3-phenyl-5-isoxazolyl)-2H-1-benzopyran-6-ol
  参考文献：
  名称：

  Isoxazole substituted chromans against oxidative stress-induced neuronal damage

  摘要：

  We have previously reported that catechol-bearing regioisomers of 5-isoxazolyl-6-hydroxy-chroman display higher in vitro neuroprotective activity, compared to hybrids with other nitrogen heterocycles, but their activity is hampered by cytotoxicity at higher concentrations. In an effort to discover non-cytotoxic isoxazole substituted chromans of high neuroprotective activity, 20 new 3- and 5-substituted (chroman-5-yl)-isoxazoles and (chroman-2-yl)-isoxazoles were synthesized using the copper(I)-catalysed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. An additional aim was to further explore the effect of the isoxazole ring substituents on the neuroprotective activity. The activity of these compounds against oxidative stress-induced death (oxytosis) of neuronal HT22 cells was evaluated and interesting SARs for this group of analogues were derived. The vast majority of new chroman analogues displayed high in vitro neuroprotective activity displaying EC(50) values below 1 mu M and lacked cytotoxicity. The position of substituents on the isoxazole ring influences the activity of the regioisomers, with the 3-aryl-5-(chroman-5-yl)-isoxazoles, 17 and 18 and bis-chroman 20 displaying higher neuroprotective activity (EC(50) similar to 0.3 mu M) compared to other (chroman-5-yl) and (chroman-2-yl)-isoxazoles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.074
• 作为产物：
  描述：

  (6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol 在 (1-重氮基-2-氧代丙基)膦酸二甲酯 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 2-ethynyl-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran
  参考文献：
  名称：

  [EN] BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY
  [FR] ACTIVATEURS BIO-INSPIRÉS DES PROTÉASOMES AYANT UNE ACTIVITÉ ANTI-ÂGE

  摘要：

  本发明涉及新型生物启发的混合化合物，其化学式为I，作为蛋白酶体激活剂并具有抗衰老活性，以及其合成方法。这些混合化合物将羟基酪醇和天然抗氧化维生素E或其生物同系物的结构特征结合在一个分子支架中。化合物I的结构包括结构蛋白酶体激活剂（通过立体化学相互作用激活），可用于生产抗衰老产品，如化妆品制剂。此外，它们可以在蛋白酶体被下调的情况和疾病中使用，以及用作蛋白酶体激活控制化合物。

  公开号：

  WO2019171088A1

文献信息

• [EN] BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY<br/>[FR] ACTIVATEURS BIO-INSPIRÉS DES PROTÉASOMES AYANT UNE ACTIVITÉ ANTI-ÂGE
  申请人：NATIONAL HELLENIC RES FOUNDATION

  公开号：WO2019171088A1

  公开（公告）日：2019-09-12

  The present invention relates to novel bio-inspired hybrid compounds of formula I which act as proteasome activators and exhibit anti-ageing activity, as well as methods for their synthesis. These hybrid compounds combine the structural features of hydroxytyrosol and the natural antioxidant vitamin E or its bioisosteres in one molecular scaffold. The compounds of formula I, which include structural proteasome activators (activation by stereochemical interaction), can be used in the production of anti-ageing products, such as cosmetic preparations. Additionally, they can be used in conditions and diseases where the proteasome is down-regulated, as well as proteasome-activation control compounds.

  本发明涉及新型生物启发的混合化合物，其化学式为I，作为蛋白酶体激活剂并具有抗衰老活性，以及其合成方法。这些混合化合物将羟基酪醇和天然抗氧化维生素E或其生物同系物的结构特征结合在一个分子支架中。化合物I的结构包括结构蛋白酶体激活剂（通过立体化学相互作用激活），可用于生产抗衰老产品，如化妆品制剂。此外，它们可以在蛋白酶体被下调的情况和疾病中使用，以及用作蛋白酶体激活控制化合物。
• Isoxazole substituted chromans against oxidative stress-induced neuronal damage
  作者：Maria Koufaki、Alexandra Tsatsaroni、Xanthippi Alexi、Helène Guerrand、Sofia Zerva、Michael N. Alexis

  DOI：10.1016/j.bmc.2011.06.074

  日期：2011.8

  We have previously reported that catechol-bearing regioisomers of 5-isoxazolyl-6-hydroxy-chroman display higher in vitro neuroprotective activity, compared to hybrids with other nitrogen heterocycles, but their activity is hampered by cytotoxicity at higher concentrations. In an effort to discover non-cytotoxic isoxazole substituted chromans of high neuroprotective activity, 20 new 3- and 5-substituted (chroman-5-yl)-isoxazoles and (chroman-2-yl)-isoxazoles were synthesized using the copper(I)-catalysed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. An additional aim was to further explore the effect of the isoxazole ring substituents on the neuroprotective activity. The activity of these compounds against oxidative stress-induced death (oxytosis) of neuronal HT22 cells was evaluated and interesting SARs for this group of analogues were derived. The vast majority of new chroman analogues displayed high in vitro neuroprotective activity displaying EC(50) values below 1 mu M and lacked cytotoxicity. The position of substituents on the isoxazole ring influences the activity of the regioisomers, with the 3-aryl-5-(chroman-5-yl)-isoxazoles, 17 and 18 and bis-chroman 20 displaying higher neuroprotective activity (EC(50) similar to 0.3 mu M) compared to other (chroman-5-yl) and (chroman-2-yl)-isoxazoles. (C) 2011 Elsevier Ltd. All rights reserved.