7-羟基-4-甲氧基甲基香豆素 | 157101-77-4

• 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-4-甲氧基甲基香豆素
• 英文名称: 7-hydroxy-4-(methoxymethyl)coumarin
• 英文别名: 7-hydroxy-4-methoxymethylycoumarin；7-Hydroxy-4-methoxymethylcoumarin；7-hydroxy-4-(methoxymethyl)chromen-2-one
• CAS: 157101-77-4
• 化学式: C₁₁H₁₀O₄
• mdl: MFCD00052607
• 分子量: 206.198
• InChiKey: PRVOZGKAZHXKMM-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128°C
• 沸点：
  392.8±42.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932209090
• 储存条件：
  保存方法：密封、阴凉、干燥处

反应信息

• 作为反应物：
  描述：

  7-羟基-4-甲氧基甲基香豆素 在 氢氧化钾 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 5-Methoxymethyl-3-methyl-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Alkoxypsoralens, Novel Nonpeptide Blockers of Shaker-Type K⁺ Channels:  Synthesis and Photoreactivity

  摘要：

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

  DOI：

  10.1021/jm981032o
• 作为产物：
  描述：

  4-甲氧基乙酰乙酸甲酯 、 间苯二酚 在 N,N-dimethylethanolammonium hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 以20%的产率得到7-羟基-4-甲氧基甲基香豆素
  参考文献：
  名称：

  胆碱离子液体是在无溶剂条件下通过Pechmann反应合成香豆素的廉价且可重复使用的催化剂†

  摘要：

  发现廉价的胆碱离子液体N，N'-二甲基氨基乙醇氢硫酸盐（[N 112 OH] [HSO 4 ]）是在无溶剂条件下进行Pechmann缩合反应的有效且可重复使用的催化剂。香豆素产物可以简单地分离，并且离子液体催化剂可以循环使用至少六次，而催化活性不会明显降低。紫外可见研究表明，增加酸度和向阳离子中引入羟基有助于乙酰乙酸乙酯的酮互变异构体的存在，从而导致[N 112 OH] [HSO 4 ]的优异性能。。

  DOI：

  10.1039/c4ra02227k

文献信息

• Coumarins as novel 17β-hydroxysteroid dehydrogenase type 3 inhibitors for potential treatment of prostate cancer
  作者：Koichiro Harada、Hideki Kubo、Yoshitaka Tomigahara、Kazuhiko Nishioka、Junya Takahashi、Mio Momose、Shinichi Inoue、Atsuyuki Kojima

  DOI：10.1016/j.bmcl.2009.10.111

  日期：2010.1

  The synthesis and SAR studies of 3- and 4-substituted 7-hydroxycoumarins as novel 17 beta-HSD3 inhibitors are discussed. The most potent compounds from this series exhibited low nanomolar inhibitory activity with acceptable selectivity versus other 17 beta-HSD isoenzymes and nuclear receptors. (c) 2009 Elsevier Ltd. All rights reserved.
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
• MEDICINAL COMPOSITION AND USAGE
  申请人：Zhou James

  公开号：US20120231097A1

  公开（公告）日：2012-09-13

  This invention provides a traditional Chinese medicine composition consisting of the extract of no more than five crude drugs, wherein crude drugs include licorice and also include Radix Scutellariae or Rhizoma Polygoni Cuspidati. In addition, this invention also provides the preparations, treatment methods, treatment applications and preparation methods of the above traditional Chinese medicine compositions.
• [EN] COMPOUNDS EXHIBITING EFFLUX INHIBITOR ACTIVITY AND COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE INHIBITRICE DE L'ECOULEMENT, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：EASTMAN CHEM CO

  公开号：WO2007115181A9

  公开（公告）日：2008-04-03

  [EN] At least one compound chosen from compounds of Formula 1: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each Of R₂, R₃, R₄ and R₅ is independently chosen from -H, alkyl, substituted aikyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z' is chosen from -O-, -N-, -NO-, - NR₄-, -S-, -SO- and -SO₂-, wherein R₄ is defined as above; each of X, X', Y and Z is independently chosen from -CR₄R₅-, -NH-, -NR₄-, -NO-. -O-, -NOR₄-, -S-, -SO-, -SO₂-, wherein R₄ and R₅ are defined as above; R₁ is chosen from a tocopherol, a steroid and a flavonoid; and R₆, is chosen from any R₁, alkyl. substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
  [FR] La présente invention concerne au moins un composé choisi parmi les composés de formule 1 : un sel ou un ester pharmaceutiquement acceptable de celui-ci, un solvate de celui-ci, un chélate de celui-ci, un complexe non covalent de celui-ci, un promédicament de celui-ci et des mélanges de ces derniers, n étant un nombre de 1 à 900, les unités individuelles pouvant être identiques ou différentes, W étant choisi parmi l'alkyle, l'alkyle substitué, le cycloalkyle, le cycloalkyle substitué, l'aryle, l'aryle substitué, l'aralkyle et l'aralkyle substitué, R₂, R₃, R₄ et R₅ étant chacun indépendamment choisi parmi -H, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué, Z' étant choisi parmi -O-, -N-, -NO-, - NR₄-, -S-, -SO- et -SO₂-, R₄ étant tel que défini ci-dessus, X, X', Y et Z étant chacun indépendamment choisi parmi -CR₄R₅-, -NH-, -NR₄-, -NO-, -O-, -NOR₄-, -S-, -SO-, -SO₂-, R₄ et R₅ étant tels que définis ci-dessus, R₁ étant choisi parmi un tocophérol, un stéroïde et un anthoxanthine, et R₆ étant choisi parmi R₁, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué.
• Alkoxypsoralens, Novel Nonpeptide Blockers of <i>Shaker</i>-Type K⁺ Channels:  Synthesis and Photoreactivity
  作者：Heike Wulff、Heiko Rauer、Tim Düring、Christine Hanselmann、Katharina Ruff、Anja Wrisch、Stephan Grissmer、Wolfram Hänsel

  DOI：10.1021/jm981032o

  日期：1998.11.1

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.