4-甲氧基吲哚-3-甲醛 | 90734-97-7

• 物质功能分类: 医药中间体
• 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-甲醛
• 中文别名: 4-甲氧基-3-吲哚甲醛；4-甲氧基-1-H-吲哚-3-甲醛
• 英文名称: 4-methoxyindole-3-carboxaldehyde
• 英文别名: 4-methoxy-1H-indole-3-carbaldehyde；3-formyl-4-methoxyindole；4-Methoxyindole-3-carbaldehyde
• CAS: 90734-97-7
• 化学式: C₁₀H₉NO₂
• mdl: MFCD00152191
• 分子量: 175.187
• InChiKey: GDVCEQRAPMIJBG-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  375.2±22.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxyindole-3-carboxaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Methoxyindole-3-carboxaldehyde
CAS number: 90734-97-7

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, under −20◦C.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H9NO2
Molecular weight: 175.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

4-甲氧基吲哚-3-甲醛是一种吲哚类衍生物，常用于作为医药中间体。

反应信息

• 作为反应物：
  描述：

  4-甲氧基吲哚-3-甲醛 在 sodium tetrahydroborate 作用下， 以95 %的产率得到4-methoxyindole-3-methanol
  参考文献：
  名称：

  腈特异性蛋白对拟南芥匀​​浆中吲哚甲醇和腈形成的影响

  摘要：

  硫代葡萄糖苷是芸苔属植物（包括芸苔属作物和拟南芥）的特殊代谢物，作为化学防御剂和促进健康的化合物引起了人们的极大兴趣。它们的生物活性主要是由于与同时存在的黑芥子酶和特异性蛋白混合时形成的分解产物，这可能导致具有不同特性的多种产物，即使是单一的芥子油苷。尽管经常报道脂肪族硫代葡萄糖苷的产品概况，但吲哚硫代葡萄糖苷分解可能导致复杂的混合物，其分析具有挑战性。本研究的目的是评估拟南芥中吲哚硫代葡萄糖苷的分解根和玫瑰花结匀浆并测试腈指定蛋白 (NSP) 对产品概况的影响。为了开发一种 GC-MS 方法来定量源自三种主要吲哚硫代葡萄糖苷的甲醇和腈，我们合成了标准品，建立了衍生化条件，确定了相对响应因子并评估了该方法对植物匀浆的适用性。我们表明甲醇在莲座丛中检测到的产物中比在野生型和 NSP1 或 NSP3 缺陷突变体的根匀浆中更占优势。NSP1 仅负责莲座丛匀浆中腈的形成，并且是根匀浆中吲哚腈形成的主要

  DOI：

  10.3390/molecules27228042
• 作为产物：
  描述：

  4-甲氧基吲哚 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 6.84h， 生成 4-甲氧基吲哚-3-甲醛
  参考文献：
  名称：

  4-、5-和6-甲氧基取代的3-锂硫代吲哚和3-吲哚锌衍生物的制备和反应

  摘要：

  报道了通过对相应的3-bromoindoles进行金属化反应制备4-, 5-和6-甲氧基取代的3-锂基-1-(三烷基硅基)吲哚4b-d，并与碘甲烷、DMF、环氧乙烷和氮化环烷进行反应。3-锂基吲哚4b-d与ZnCl2的转金属化反应生成3-吲哚基锌氯化物11b-d，这些化合物经过Pd(0)催化的交叉偶联反应与2-卤吡啶反应，生成4-, 5-和6-甲氧基取代的3-(2-吡啶基)吲哚。

  DOI：

  10.1055/s-2001-10812

文献信息

• Access to Polycyclic Indol(en)ines <i>via</i> <scp>Base‐Catalyzed</scp> Intramolecular Dearomatizing <scp>3‐Alkenylation</scp> of Alkynyl Indoles
  作者：Lin Lu、Zuoliang Zheng、Yongjie Yang、Bo Liu、Biaolin Yin

  DOI：10.1002/cjoc.202100164

  日期：2021.8

  Polycyclic indolines and indolenines were synthesized via base-catalyzed intramolecular dearomatizing 3-alkenylation reactions of alkynyl indoles 1 at room temperature. The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines 2. The imine functionality of 2 could undergo

  多环的二氢吲哚和假吲哚合成通过在室温下炔基吲哚1的碱催化的分子内dearomatizing 3-烯基化反应。碱增强了吲哚部分 3 位碳的亲核性，促进与炔烃的独家 5- exo- dig 环化反应形成螺吲哚 2。 2 的亚胺官能团可以进行原位亲核加成形成螺吲哚3 当 R 是氨基甲酰基或还原形成螺二氢吲哚时 4 当 R 是 H 时。
• Method for Producing Intermediates for the Production of Novel Macrocycles that are Inhibitors of the Proteasomic Degradation of p27, such as Argyrin and Derivatives Thereof, and Uses of Said Macrocycles
  申请人：Kalesse Markus

  公开号：US20110311564A1

  公开（公告）日：2011-12-22

  The present invention relates to the use of particular macrocycles that are inhibitors of the proteasomic degradation of p27, in particular argyrin and derivatives thereof, for a treatment in a variety of conditions, such as the induction of immunotolerance, autoimmune diseases, bacterial infections, and proliferative diseases, such as cancers.

  本发明涉及使用特定的大环化合物，这些大环化合物是p27蛋白质降解的蛋白酶体抑制剂的抑制剂，尤其是精胺及其衍生物，用于治疗多种病症，如诱导免疫耐受、自身免疫疾病、细菌感染以及增殖性疾病，如癌症。
• Structure-Guided Design, Synthesis, and Biological Evaluation of (2-(1<i>H</i>-Indol-3-yl)-1<i>H</i>-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) Analogues Targeting the Colchicine Binding Site in Tubulin
  作者：Qinghui Wang、Kinsie E. Arnst、Yuxi Wang、Gyanendra Kumar、Dejian Ma、Stephen W. White、Duane D. Miller、Weimin Li、Wei Li

  DOI：10.1021/acs.jmedchem.9b00706

  日期：2019.7.25

  10ab and 10bb in complex with tubulin confirmed their improved molecular interactions to the colchicine site. In vitro, biological studies showed that new ABI-231 analogues disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analogue 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft

  ABI-231是一种有效的，口服生物利用的微管蛋白抑制剂，可与秋水仙碱结合位点相互作用，目前正在接受前列腺癌的临床试验。在与微管蛋白复合的ABI-231晶体结构的指导下，我们围绕3-吲哚部分进行了结构-活性关系研究，从而发现了几种有效的ABI-231类似物，最著名的是10ab和10bb。与微管蛋白复合的10ab和10bb的晶体结构证实了它们与秋水仙碱位点的分子相互作用得到了改善。在体外，生物学研究表明，新的ABI-231类似物可破坏微管蛋白聚合，促进微管碎裂并抑制癌细胞迁移。体内，类似物10bb不仅在黑素瘤异种移植模型中显着抑制原发性肿瘤生长并减少肿瘤转移，而且在抗紫杉烷的PC-3 / TxR模型中显示出显着的克服紫杉醇抗性的能力。此外，药理学筛选表明10bb潜在脱靶功能的风险较低。
• Dissecting metabolic puzzles through isotope feeding: a novel amino acid in the biosynthetic pathway of the cruciferous phytoalexins rapalexin A and isocyalexin A
  作者：M. Soledade C. Pedras、Estifanos E. Yaya

  DOI：10.1039/c2ob27076e

  日期：——

  Understanding defence pathways of plants is crucial to develop disease-resistant agronomic crops, an important element of sustainable agriculture. For this reason, natural plant defenses such as phytoalexins, involved in protecting plants against microbial pathogens, have enormous biotechnological appeal. Crucifers are economically important plants, with worldwide impact as oilseeds, vegetables of great dietetic value and even nutraceuticals. Notably, the intermediates involved in the biosynthetic pathways of unique cruciferous phytoalexins such as rapalexin A and isocyalexin A remain unknown. Toward this end, using numerous perdeuterated compounds, we have established the potential precursors of these unique phytoalexins and propose for the first time their detailed biosynthetic pathway. This pathway involves a variety of intermediates and a novel amino acid as the central piece of this complex puzzle. This work has set the stage for the discovery of enzymes and genes of the biosynthetic pathway of cruciferous phytoalexins of unique scaffolds.

  理解植物的防御途径对于开发抗病农作物至关重要，这是可持续农业的重要组成部分。因此，天然植物防御物质，如植物抗毒素（参与保护植物免受微生物病原体侵害），具有巨大的生物技术吸引力。十字花科植物是具有重要经济价值的植物，在全球范围内作为油料、高营养价值的蔬菜甚至保健品产生影响。值得注意的是，在独特的十字花科植物抗毒素（如芸薹素A和异硫氰酸酯A）的生物合成途径中所涉及的中间体仍未知。为此，我们利用大量氘代化合物确立了这些独特植物抗毒素的可能前体，并首次提出了它们的详细生物合成途径。该途径涉及多种中间体和一种作为这一复杂拼图核心的新型氨基酸。这项工作为发现具有独特骨架的十字花科植物对抗毒素生物合成途径的酶和基因奠定了基础。
• Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents
  作者：Shun Zhang、Baijiao An、Jiayan Li、Jinhui Hu、Ling Huang、Xingshu Li、Albert S. C. Chan

  DOI：10.1039/c7ob01655g

  日期：——

  chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 25b exhibited the most potent antiproliferative activities against six human cancer cell lines with IC50 values of 0.004–0.022 μM. A microtubule dynamics assay and an immunofluorescence assay confirmed that 25b could effectively inhibit tubulin polymerization (IC50 = 2.1 ± 0.27 μM)

  合成了十六种新的含硒的吲哚查尔酮和二芳基酮衍生物，并将其评估为微管蛋白聚合抑制剂。其中，化合物25b对六种人类癌细胞系表现出最有效的抗增殖活性，IC 50值为0.004-0.022μM。微管动力学分析和免疫荧光分析证实25b可有效抑制微管蛋白聚合（IC 50 = 2.1±0.27μM）。进一步的细胞机制研究表明25b诱导了G2 / M期阻滞，线粒体膜电位（MMP）的降低进一步证明了这一点。