8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid | 123254-19-3

• 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: 8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid
• 英文别名: 8-MeO-6-NO2CcaH；8-Methoxy-6-nitro-2-oxo-2H-chromen-3-carbonsaeure；8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid；8-methoxy-6-nitro-2-oxochromene-3-carboxylic acid
• CAS: 123254-19-3
• 化学式: C₁₁H₇NO₇
• 分子量: 265.179
• InChiKey: AQNRIYUGMHAEMV-UHFFFAOYSA-N

物化性质

• 熔点：
  224-227 °C(Solvent: Water ; Ethanol)
• 沸点：
  539.8±50.0 °C(Predicted)
• 密度：
  1.625±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid 在 氯化亚砜 、 苯 作用下， 生成 8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid diethylamide
  参考文献：
  名称：

  Coumarins. I. Derivatives of Coumarin-3- and 4-Carboxylic Acids

  摘要：

  DOI：

  10.1021/ja01179a007
• 作为产物：
  描述：

  8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 生成 8-methoxy-6-nitro-2-oxo-2H-chromene-3-carboxylic acid
  参考文献：
  名称：

  Coumarins. I. Derivatives of Coumarin-3- and 4-Carboxylic Acids

  摘要：

  DOI：

  10.1021/ja01179a007

文献信息

• A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones
  作者：Aimin Song、Xiaobing Wang、Kit S Lam

  DOI：10.1016/s0040-4039(03)00108-4

  日期：2003.2

  Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

  在乙醇中回流2小时后，从邻羟基苯甲醛和Meldrum酸以高收率获得了香豆素-3-羧酸。反应性较低的酮首先与乙醇氨反应形成酮亚胺，然后与Meldrum's酸缩合以生成中等收率的4-烷基香豆素-3-羧酸。
• Design, Spectroscopy, and Assessment of Cholinesterase Inhibition and Antimicrobial Activities of Novel Coumarin–Thiadiazole Hybrids
  作者：Dariusz Karcz、Karolina Starzak、Ewa Ciszkowicz、Katarzyna Lecka-Szlachta、Daniel Kamiński、Bernadette Creaven、Anna Miłoś、Hollie Jenkins、Lidia Ślusarczyk、Arkadiusz Matwijczuk

  DOI：10.3390/ijms23116314

  日期：——

  comparable to that of known coumarin-based fluorescence standards. Moreover, the new compounds were tested as potential antineurodegenerative agents via their ability to act as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. Compared to the commercial standards, only a few compounds demonstrated moderate AChE and BuChE activities. Moreover, the novel derivatives were tested for

  使用多种光谱技术和 XRD 晶体学分离并充分表征了衍生自取代香豆素-3-羧酸的一系列新型香豆素-噻二唑杂化物。几种新型化合物在可见光区域显示出强烈的荧光，与已知的基于香豆素的荧光标准相当。此外，这些新化合物通过它们作为乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 抑制剂的能力被测试为潜在的抗神经退行性疾病。与商业标准相比，只有少数化合物表现出中等的 AChE 和 BuChE 活性。此外，还测试了这些新型衍生物对一组病原细菌和真菌物种的抗菌活性。
• Novel coumarin-amide derivatives and its preparation, said drug composition and its use
  申请人：Xu Shiping

  公开号：US20060148834A1

  公开（公告）日：2006-07-06

  The present invention relates to novel coumarin derivatives, their carboxamides, pharmaceutical compositions containing them and their uses as drugs for kidney protection, treating drugs of hypertension, cardio-cerebrovascular diseases, non-insulin dependent diabetes, tumor, pre-cancerous lesion, and edemas.

  本发明涉及新型香豆素衍生物，它们的羧酰胺，包含它们的制药组合物以及它们作为肾脏保护药物、治疗高血压、心脑血管疾病、非胰岛素依赖性糖尿病、肿瘤、癌前病变和水肿的用途。
• THE NOVEL COUMARIN-AMIDE DERIVATIVES AND ITS PREPARATION, SAID DRUG COMPOSITION AND ITS USE
  申请人：THE INSTITUTE OF MATERIA MEDICA OF CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP1570846A1

  公开（公告）日：2005-09-07

  The present invention relates to novel coumarin derivatives, their carboxamides, pharmaceutical compositions containing them and their uses as drugs for kidney protection, treating drugs of hypertension, cardio-cerebrovascular diseases, non-insulin dependent diabetes, tumor, pre-cancerous lesion, and edemas.

  本发明涉及新型香豆素衍生物、其羧酰胺、含有它们的药物组合物及其作为保护肾脏、治疗高血压、心脑血管疾病、非胰岛素依赖型糖尿病、肿瘤、癌前病变和水肿药物的用途。
• Novel 2H-chromen-2-one-3-carboxamides for medical uses
  申请人：THE INSTITUTE OF MATERIA MEDICA OF CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：EP2295053A1

  公开（公告）日：2011-03-16

  The present invention relates to novel coumarin derivatives, their carboxamides, pharmaceutical compositions containing them, and their uses as drugs for kidney protection, treating drugs of hypertension, cardio-cerebrovascular diseases, non-insulin dependent diabetes, tumor, pre-cancerous lesion, and edemas. Claimed are compounds of general formula (I): wherein R3 is selected from the group consisting , CONHR9 R4 is selected from the group consisting of hydrogen, CONHR10, R5 is selected from the group consisting of H, and C1-C4 alkyl; R6 is selected from the group consisting of H, C1-C12 alkyl, halogen, NO2, and CONHR13, R8 is selected from the group consisting of H, C1-C4 alkyl or alkoxyl, NO2. The other variables are as defined in claims.

  本发明涉及新型香豆素衍生物、它们的羧酰胺、含有它们的药物组合物，以及它们作为保护肾脏的药物、治疗高血压、心脑血管疾病、非胰岛素依赖型糖尿病、肿瘤、癌前病变和水肿的药物的用途。 所要求的是通式(I)化合物： 其中 R3 选自以下组成的组 CONHR9 R4 选自由氢、CONHR10 组成的组 R5 选自由 H 和 C1-C4 烷基组成的组； R6 选自由 H、C1-C12 烷基、卤素、NO2 和 CONHR13 组成的组、 R8选自由H、C1-C4烷基或烷氧基、NO2组成的组。 其他变量如权利要求中所定义。