6-methoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde | 113078-09-4

• 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-2,5,7,8-tetramethylchroman-2-carbaldehyde
• 英文别名: 3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-carboxaldehyde；6-Methoxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbaldehyde
• CAS: 113078-09-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: QTPHKTCRXQLGRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde 在 吡啶 、 copper(ll) sulfate pentahydrate 、 三氟二甲基硫醚络合物 、 盐酸羟胺 、 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-[5-(4-methoxyphenyl)-3-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 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 6-methoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde
  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

• Nitrone derivatives of trolox as neuroprotective agents
  作者：György T. Balogh、Krisztina Vukics、Árpád Könczöl、Ágnes Kis-Varga、Anikó Gere、János Fischer

  DOI：10.1016/j.bmcl.2005.04.043

  日期：2005.6

  Synthesis of nitrone derivatives of trolox is described. Their biological evaluation was performed in vitro for scavenging different free radicals, inhibiting Fe2+-induced lipid peroxidation, and in vivo in a permanent middle cerebral artery occlusion model in mice. New compounds exert pharmacological activities comparable to or better than those of trolox or nitrone-type reference compounds. (c) 2005 Elsevier Ltd. All rights reserved.
• Fluorogenic α-Tocopherol Analogue for Monitoring the Antioxidant Status within the Inner Mitochondrial Membrane of Live Cells
  作者：Katerina Krumova、Lana E. Greene、Gonzalo Cosa

  DOI：10.1021/ja408227f

  日期：2013.11.13

  We report here the preparation of a lipophilic fluorogenic antioxidant (Mito-Boclipy-TOH) that targets the inner mitochondrial lipid membrane (IMM) and is sensitive to the presence of lipid peroxyl radicals, effective chain carriers in the lipid chain autoxidation. Mito-Bodipy-TOH enables monitoring of the antioxidant status, i.e., the antioxidant load and ability to prevent lipid chain autoxidation, within the inner mitochondrial membrane of live cells. The new probe consists of 3 segments: a receptor, a reporter, and a mitochondria-targeting element, constructed, respectively, from an alpha-tocopherol-like chromanol moiety, a BODIPY fluorophore, and a triphenylphosphonium cation (TPP). The chromanol moiety ensures reactivity akin to that of a-tocopherol, the most potent naturally occurring lipid soluble antioxidant, while the BODIPY fluorophore and TPP ensure partitioning within the inner mitochondrial membrane. Mechanistic studies conducted either in homogeneous solution or in liposomes and in the presence of free radical initiators show that the antioxidant activity of Mito-Bodipy-TOH is on par with that of a-tocopherol. Studies conducted on live fibroblast cells further show the antioxidant depletion in the presence of methyl viologen (paraquat), a known agent of oxidative stress and source of superoxide radical anion (and indirectly, a causative of lipid peroxidation) within the mitochondria matrix. We recorded a ca. 8-fold emission enhancement with Mito-Bodipy-TOH in cells stressed with methyl viologen, whereas no enhancement was observed in control studies with untreated cells. Our findings underscore the potential of the new fluorogenic antioxidant Mito-Bodipy-TOH to study the chemical link between antioxidant load, lipid peroxidation and mitochondrial physiology.
• EHDZIRI, KATSUDZI;KANAXIRA, KOITI;SIONO, MANDZO;FUDZITA, JOSIDZI;YAMAXARA+
  作者：EHDZIRI, KATSUDZI、KANAXIRA, KOITI、SIONO, MANDZO、FUDZITA, JOSIDZI、YAMAXARA+

  DOI：——

  日期：——