4-甲氧基吲哚-3-乙酸甲酯 | 142653-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-甲氧基吲哚-3-乙酸甲酯
• 英文名称: methyl 4-methoxyindole-3-acetate
• 英文别名: methyl 4-methoxyindolyl-3-acetate；methyl 2-(4-methoxy-1H-indol-3-yl)acetate
• CAS: 142653-08-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: NWALYIKBPXGTJR-UHFFFAOYSA-N

物化性质

• 沸点：
  379.7±27.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基吲哚-3-乙酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 、 正己烷 、 苯 为溶剂， 反应 1.33h， 生成 O-甲基赛洛新
  参考文献：
  名称：

  Sakagami, Hideki; Ogasawara, Kunio, Heterocycles, 1999, vol. 51, # 5, p. 1131 - 1135

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基吲哚 在 palladium on activated charcoal sodium hypophosphite 、 三乙胺 、 异丁酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 54.0h， 生成 4-甲氧基吲哚-3-乙酸甲酯
  参考文献：
  名称：

  Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana

  摘要：

  Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-beta-D-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-elect ro spray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these;imino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.04.030

文献信息

• Elucidation of the Structure and Synthesis of Neuroprotective Low Molecular Mass Components of the <i>Parawixia bistriata</i> Spider Venom
  作者：Yvonne M. Forster、Jennifer Leigh Green、Apeksha Khatiwada、José Luiz Liberato、Poli Adi Narayana Reddy、Joseph M. Salvino、Stefan Bienz、Laurent Bigler、Wagner Ferreira dos Santos、Andréia Cristina Karklin Fontana

  DOI：10.1021/acschemneuro.0c00007

  日期：2020.6.3

  HPLC fractions that demonstrate this bioactivity. Pwx1 stimulates l-glutamate uptake through the main transporter in the brain, EAAT2, and is neuroprotective in in vivo glaucoma models. Pxw2 inhibits GABA and glycine uptake in synaptosomes and inhibits seizures and neurodegeneration, and Pwx10 increases l-glutamate uptake in synaptosomes and is neuroprotective and anticonvulsant, shown in in vivo epilepsy

  南美社交蜘蛛Parawixia bistriata产生的毒液中含有具有有趣生物活性的复杂有机化合物。粗毒会导致白蚁麻痹，并刺激大鼠谷氨酸突触体中的1-谷氨酸摄取并抑制GABA摄取。谷氨酸是昆虫神经肌肉连接处和哺乳动物中枢神经系统的主要神经递质，表明该毒液可调节谷氨酸能系统。Parawixin1、2和10（Pwx1、2和10）是证明这种生物活性的HPLC馏分。Pwx1提神升谷氨酸盐摄取通过在大脑中，EAAT2主要转运蛋白，并且是在神经保护体内青光眼模型。Pxw2抑制突触小体中的GABA和甘氨酸摄取，并抑制癫痫发作和神经退行性变，Pwx10增加突触小体中的1-谷氨酸摄取，并且在体内癫痫模型中具有神经保护作用和抗惊厥作用。在这里，我们研究了这种毒液中的低分子量化合物，发现了20多种小化合物和36种独特的带有或不带有氨基酸接头的酰基多胺。馏分Pwx1和Pwx2中的活性物质需要进一步研究。我们阐明并
• Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana
  作者：Kenji Kai、Junko Horita、Kyo Wakasa、Hisashi Miyagawa

  DOI：10.1016/j.phytochem.2007.04.030

  日期：2007.6

  Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-beta-D-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-elect ro spray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these;imino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis. (c) 2007 Elsevier Ltd. All rights reserved.
• Sakagami, Hideki; Ogasawara, Kunio, Heterocycles, 1999, vol. 51, # 5, p. 1131 - 1135
  作者：Sakagami, Hideki、Ogasawara, Kunio

  DOI：——

  日期：——