7-羟基香豆素-3-羧酸 | 56437-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 7-羟基香豆素-3-羧酸
• 中文别名: 6-羟基-2-氧代-2H-色烯-3-羧酸
• 英文名称: 3-carboxy-6-hydroxycoumarin
• 英文别名: Pre pre1 2;5;6；6-hydroxy-3-carboxycoumarine；6-hydroxy-2-oxo-2H-chromene-3-carboxylic acid；6-Hydroxy-2-oxo-2H-chromen-3-carbonsaeure；6-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid；6-hydroxy-2-oxochromene-3-carboxylic acid
• CAS: 56437-16-2
• 化学式: C₁₀H₆O₅
• 分子量: 206.155
• InChiKey: SLPOZBYDRWPSBE-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C(Solv: ethanol (64-17-5))
• 沸点：
  490.4±45.0 °C(Predicted)
• 密度：
  1.639±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

制备方法与用途

3-羧基-6-羟基香豆素是有机合成中的重要中间体。

反应信息

• 作为反应物：
  描述：

  7-羟基香豆素-3-羧酸 在 氯化亚砜 作用下， 生成 6-Hydroxy-2-oxochromene-3-carbonyl chloride
  参考文献：
  名称：

  Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

  摘要：

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.024
• 作为产物：
  描述：

  6-hydroxy-2-oxo-2H-chromene-3-carbonitrile 在 碳酸氢钠 作用下， 反应 3.0h， 生成 7-羟基香豆素-3-羧酸
  参考文献：
  名称：

  One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water

  摘要：

  通过一步法，将适当取代的水杨醛与丙二腈在水中反应，成功制备了氯代、羟基、甲氧基和叔丁基取代的3-羧基香豆素。总体产率较高，且该方法无需使用有机溶剂。

  DOI：

  10.1055/s-2003-41061

文献信息

• Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
  作者：Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi、Saeed Baghery

  DOI：10.1039/c5ra14001c

  日期：——

  Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

  利用纳米结构有机催化剂，即2-氨基甲酰肼-1-磺酸和氨基甲酰磺酸，直接绿色合成4,4′-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的方法已经被开发出来。

• Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
  作者：Daniela Secci、Simone Carradori、Adriana Bolasco、Paola Chimenti、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2011.07.017

  日期：2011.10

  Several 3-carbonyl (1–26), 3-acyl (27–52), and 3-carboxyhydrazido (53–58) coumarins have been synthesized in high yields (72–99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl

  几个-3-羰基（1 - 26），3-酰基（27 - 52），和3- carboxyhydrazido（53 - 58）香豆素已经以高收率（72-99％）合成并测试在体外对它们的人类单胺氧化酶A和B（hMAO-A和hMAO-B）的抑制活性。评价了香豆素核上的不同取代基对生物活性和同工型选择性的影响。对于使用IC 50获得高效且选择性的hMAO-B抑制剂而言，在3-乙酯香豆素环的C7位取代或在C3引入肼基取代基很重要。值在纳摩尔范围内。一些衍生物也进行了稳定性测试，在体外没有化​​学裂解。
• A Facile One-Pot Synthesis of Chromen-2-one Derivatives Fused with Five Membered Heterocycles
  作者：S. Tasqeeruddin、Abdullah S. Al-Arifi、P.K. Dubey

  DOI：10.14233/ajchem.2013.14948

  日期：——

  A facile one-pot synthesis of 3-benzoxazol-2-yl-chromen-2-ones (4) by the condensation of chromen-2-one-3-carboxylates (1) with o-hydroxy aniline (3) is being reported in this paper. Alternatively 3-benzoxazol-2-yl-chromen-2-ones are prepared from chromen-2-one-3-carboxylic acids (2). The structures of all the products have been established by their spectral and analytical data.

  本文报告了一种通过铬烯-2-酮-3-羧酸（1）与邻羟基苯胺（3）缩合，一步合成 3-苯并恶唑-2-基苯并吡喃-2-酮（4）的简便方法。另外，3-苯并恶唑-2-基色烯-2-酮也是由铬烯-2-酮-3-羧酸（2）制备的。所有产物的结构均已通过光谱和分析数据确定。
• Coumarin-Fused Coumarin: Antioxidant Story from <i>N</i>,<i>N</i>-Dimethylamino and Hydroxyl Groups
  作者：Gao-Lei Xi、Zai-Qun Liu

  DOI：10.1021/acs.jafc.5b00399

  日期：2015.4.8

  the inhibitory effect of coumarin-fused coumarin on AAPH-induced oxidation of DNA about 3 times higher than a single hydroxyl group, whereas N,N-dimethylamino-substituted coumarin-fused coumarin possessed high activity toward •OH-induced oxidation of DNA without the hydroxyl group contained. Therefore, the hydroxyl group together with N,N-dimethylamino group may be a novel combination for the design

  通过与内酯中的C═C共享，两个香豆素骨架可以形成chromeno [3,4- c ] chromene-6,7-dione。本发明的目的是通过含有羟基和N，N-二甲基氨基作为官能团的六种合成化合物来探索香豆素融合的香豆素的抗氧化作用。2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸盐）阳离子自由基（ABTS +•），2,2'-二苯基-1-吡啶并肼基自由基（DPPH）和Galvinoxyl自由基的猝灭能力表明速率常数清除自由基的方法与香豆素融合的香豆素支架中的羟基含量有关。但是香豆素融合的香豆素能够抑制由• OH，Cu 2+引起的DNA氧化/谷胱甘肽（GSH）和2,2'-偶氮双（2-ami基丙烷盐酸盐）（AAPH），即使在没有羟基的情况下也是如此。特别地，羟基和位于不同苯环上的N，N-二甲基氨基基团提高了香豆素稠合的香豆素对AAPH诱导的DNA氧化的抑制作用，其抑制作用比单个羟基基团高约3倍
• A Simple One-Pot Synthesis of Fully Substituted 1<i>H</i> -Pyridone[<i>1</i> ,2-a]-Fused-1,3-Diazaheterocycles
  作者：Mohammad Bayat、Monireh Rezaee、Long-Guan Zhu

  DOI：10.1002/jhet.2877

  日期：2017.9

  An efficient procedure for the synthesis of 7‐(aryl)‐8‐nitro‐2,3,6,7‐tetrahydroimidazo[1,2‐a]pyridinones, 8‐(aryl)‐9‐nitro‐3,4,7,8‐tetrahydropyridone[1,2‐a]pyrimidines and 9‐(aryl)‐10‐nitro‐2,3,4,5,8,9‐hexahydropyridone[1,2‐a]diazepine via one‐pot three component reaction of diamine, nitroketene dithioacetal (1,1‐bis(methylsulfanyl)‐2‐nitroethene), and coumarine‐3‐ carboxylic acid derivatives in EtOH

  合成7-（芳基）-8-硝基-2,3,6,7-四氢咪唑并[1,2-a]吡啶酮，8-（芳基）-9-硝基-3,4,7的有效方法一锅三组分的8,4-四氢吡啶酮[1,2-a]嘧啶和9-（芳基）-10-硝基-2-3,4,5,8,9-六氢吡啶酮[1,2-a]二氮杂据报道在回流条件下二胺，硝基烯酮二硫缩醛（1,1-双（甲基硫烷基）-2-硝基乙烯）和香豆碱-3-羧酸衍生物在EtOH中的反应。该方法的优点是简单，易于纯化，收率高和无催化剂条件。所有产品均通过1 H和13 C-NMR，IR，MS和X射线晶体结构分析确认。