4-methyl-2-oxo-2H-chromen-7-yl benzoate | 66185-72-6

• 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
• 英文名称: 4-methyl-2-oxo-2H-chromen-7-yl benzoate
• 英文别名: (4-Methyl-2-oxochromen-7-yl) benzoate
• CAS: 66185-72-6
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: JPNMSSAADBXSRO-UHFFFAOYSA-N

物化性质

• 熔点：
  159 °C
• 沸点：
  458.3±40.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxo-2H-chromen-7-yl benzoate 在 sodium hydroxide 、 三氯化铝 作用下， 生成 (2,6-dimethoxyphenyl)(phenyl)methanone
  参考文献：
  名称：

  Limaye, Chemische Berichte, 1934, vol. 67, p. 12,14

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 生成 4-methyl-2-oxo-2H-chromen-7-yl benzoate
  参考文献：
  名称：

  SALUNKHE D. G.; MANE R. B.; JAGDALE M. H.; SALUNKHE M. M., CURR. SCI., 55,(1986) N 17, 853-854

  摘要：

  DOI：

文献信息

• An Efficient, Mild and Scalable Synthesis of Bioactive Compounds Containing the Angelicin Scaffold
  作者：Shiao Hui-Yi、Kuo Ching-Chuan、Horng Jim-Tong、Shih Shin-Ru、Chang Sui-Yuan、Liao Chun-Chen、Hsu John T.-A.、Amancha Prashanth Kumar、Chao Yu-Sheng、Hsieh Hsing-Pang

  DOI：10.1002/jccs.201200233

  日期：2012.12

  An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically harsh conditions. The new methodology is applied to the synthesis of several, previously reported analogs of angelicin which have potent anti‐influenza

  开发了一种高效，温和且可扩展的基于安吉林支架的化合物合成方法。特别地，此处描述的新合成路线避免了先前报告的关键Fries重排步骤的需要，该步骤使用了不切实际的苛刻条件。新的方法学被用于合成许多先前报道的具有强力抗流感和抗癌活性的当归霉素类似物。
• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING VIRAL INFECTION
  申请人：Hsieh Hsing-Pang

  公开号：US20090312406A1

  公开（公告）日：2009-12-17

  A method for treating an infection with a virus. The method includes administering to a subject in need thereof an effective amount of one or more coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a pharmaceutical composition including a coumarin compound.

  一种治疗病毒感染的方法。该方法包括向需要的受试者施用一种或多种符合以下化学式（I）的香豆素化合物的有效量：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了包括香豆素化合物的药物组合物。
• A High-Throughput, Low-Volume Enzyme Assay on Solid Support
  作者：Peter Babiak、Jean-Louis Reymond

  DOI：10.1021/ac048611n

  日期：2005.1.1

  water-soluble substrates (glycosidases), whole-protein substrates (proteases), and enzyme inhibition measurements. Hydrolytically labile umbelliferyl esters can be used to assay lipases in this format without background hydrolysis. High throughput and reproducibility were tested by fingerprint analysis of lipases and esterases against 37 different fluorogenic ester substrates. A set of eight fluorogenic unbelliferyl

  描述了一种高通量酶测定法，该测定法每次测试使用1微升或更少的酶溶液。酶溶液通过机器人处理以超过1000次/小时的处理量沉积在已预浸渍有荧光底物的硅胶板表面上。通过荧光定量反应。该方法与水不溶性底物（脂肪酶），水溶性底物（糖苷酶），全蛋白底物（蛋白酶）和酶抑制测量兼容。水解不稳定的伞形酯可用于以这种形式测定脂肪酶，而无需进行背景水解。通过对37种不同的荧光酯底物进行脂肪酶和酯酶的指纹分析，测试了高通量和可重复性。
• Synthesis and Evaluation of Substituted 4-methyl-2-oxo-2H-chromen-7-yl Phenyl Carbamates as Potent Acetylcholinesterase Inhibitors and Anti- Amnestic Agents
  作者：Preet Anand、Baldev Singh

  DOI：10.2174/1573406411309050009

  日期：2013.6.1

  The study aimed to synthesize and evaluate substituted 4-methyl-2-oxo-2H-chromen-7-yl phenylcarbamates as potent acetylcholinesterase (AChE) inhibitors and anti-amnestic agents. The compounds were evaluated for AChE and butyrylcholinesterase (BuChE) inhibitory activity in rat brain homogenate and plasma, respectively. The most potent test compound 4d was evaluated for memory testing in scopolamine-induced amnesia. The phenylcarbamate substituted coumarins (4a-4h) demonstrated more potent AChE inhibitory as compared to parent 7-hydroxy-4-methylcoumarin. The introduction of phenylcarbamate moiety to coumarin template also significantly increased BuChE inhibitory activity, albeit less than AChE inhibitory activity with approximate BuChE/AChE selectivity ratio of 20. The compound 4d displayed the most potent AChE inhibitory activity with IC50 = 13.5 ± 1.7 nM, along with amelioration of amnesia in mice in terms of restoration of time spent in target quadrant and escap latency time. It is concluded that carbamate derivatives of coumarin may be employed as potential AChE inhibitors and anti-amnestic agents.

  本研究旨在合成并评估取代的4-甲基-2-氧-2H-色烯-7-基苯基氨基甲酸酯类化合物作为有效的乙酰胆碱酯酶（AChE）抑制剂和抗遗忘剂。这些化合物分别在 rat 脑组织匀浆和血浆中评估了其对 AChE 和丁酰胆碱酯酶（BuChE）的抑制活性。最强的测试化合物 4d 在东莨菪碱诱导的遗忘症中进行了记忆测试。苯基氨基甲酸酯取代的香豆素（4a-4h）相对于母体 7-羟基-4-甲基香豆素的 AChE 抑制活性更强。将苯基氨基甲酸酯部分引入香豆素模板也显著增加了 BuChE 抑制活性，尽管这一活性不及 AChE 抑制活性，大约有 20 的 BuChE/AChE 选择性比。化合物 4d 显示出最强的 AChE 抑制活性，IC50 = 13.5 ± 1.7 nM，并能改善小鼠的遗忘症状，体现在在目标象限停留时间的恢复和逃避延迟时间的缩短。可以得出结论，香豆素的氨基甲酸酯衍生物可能被用作潜在的 AChE 抑制剂和抗遗忘剂。
• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING CANCER
  申请人：Hsieh Hsing-Pang

  公开号：US20090312317A1

  公开（公告）日：2009-12-17

  Coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a method for treating cancer with coumarin compounds.

  公式（I）的香豆素化合物：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了一种使用香豆素化合物治疗癌症的方法。