7-chloro-4-coumarinylacetic acid | 68747-28-4

• 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
• 英文名称: 7-chloro-4-coumarinylacetic acid
• 英文别名: 7-Chlor-cumarin-4-essigsaeure；(7-chloro-2-oxo-2H-chromen-4-yl)-acetic acid；(7-Chloro-2-oxo-2H-chromen-4-yl)-acetic acid；2-(7-chloro-2-oxochromen-4-yl)acetic acid
• CAS: 68747-28-4
• 化学式: C₁₁H₇ClO₄
• 分子量: 238.627
• InChiKey: NXDDONCNRKVQOO-UHFFFAOYSA-N

物化性质

• 沸点：
  462.8±45.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-4-coumarinylacetic acid 在 哌啶 作用下， 生成
  参考文献：
  名称：

  Moorthy, J. Narasimha; Samant, S. D.; Venkatesan, K., Journal of the Chemical Society. Perkin transactions II, 1994, # 6, p. 1223 - 1228

  摘要：

  DOI：
• 作为产物：
  描述：

  柠檬酸 在 硫酸 作用下， 反应 38.5h， 生成 7-chloro-4-coumarinylacetic acid
  参考文献：
  名称：

  新型7-卤代香豆素-4-乙酸衍生物的合成及其抗肿瘤潜力

  摘要：

  基于香豆素框架的化合物引起了广泛的研究关注，这不仅因为其结构的多样性，还因为其生物活性的多元性。在本报告中，合成了四种7-卤-4-香豆酰乙酸衍生物，分别称为RY1-RY4，并通过所采用的分光光度计确认了它们的化学骨架。利用名为pre-ADMET的免费在线软件，对合成的卤代香豆素的药代动力学特征进行了体外检查。利用5-氟尿嘧啶作为参照药物，并基于MTT法作为对八种标准肿瘤细胞系的可视指示剂，评估了合成卤代香豆素的潜在抗肿瘤应用能力。从这一评估中获得的结果表明，除RY1外，合成卤代香豆素作为抗肿瘤剂的影响较标准药物为低。此外，卤代香豆素对测试细胞系的活性显示出大致相同的方式，最大的抑制作用报告对MCF-7和HeLa细胞系。从计算的药代动力学数据及抗肿瘤评估展示的结果来看，作者得出结论：合成的卤代香豆素，尤其是RY1，具有作为抗肿瘤剂的潜在申请者，具有广泛活性的可能。此外，化合物RY1和RY2可能为合成针对乳腺癌和宫颈癌表型具有强大抗肿瘤活性的药物提供高价值的骨架。

  DOI：

  10.21608/ejchem.2021.68873.3508

文献信息

• Regiospecific Normal Diels-Alder Reaction of trans-1,2-Biscoumarinylethenes
  作者：Shriniwas Samant、Kailas Sanap

  DOI：10.1055/s-0031-1290454

  日期：——

  The reaction of different 7,8-substituted coumarin 4-acetic acids with 7-diethylaminocoumarin-3-carbaldehyde in the presence of piperidine in methanol gives 1,2-biscoumarinylethenes. These compounds undergo regiospecific Diels–Alder reactions at their electron-rich diene components C 3 –C 4 –C 10 –C 9 , with electron-deficient dienophiles. The feasibility of normal electron-demand Diels–Alder reactions

  在哌啶的存在下，不同的 7,8-取代香豆素 4-乙酸与 7-二乙基氨基香豆素-3-甲醛反应得到 1,2-双香豆素乙烯。这些化合物在其富电子二烯组分 C 3 –C 4 –C 10 –C 9 处与缺电子亲二烯体发生区域特异性 Diels-Alder 反应。正常电子需求 Diels-Alder 反应的可行性可以基于 HOMO-LUMO 间隙来解释。所有的化合物都是新的并且颜色很深。
• Synthesis and rat lens aldose reductase inhibitory activity of some benzopyran-2-ones
  作者：Abram N. Brubaker、Jack De Ruiter、William L. Whitmer

  DOI：10.1021/jm00156a031

  日期：1986.6

  A number of 4,7-disubstituted benzopyran-2-ones were synthesized and evaluated for crude rat lens aldose reductase inhibitory activity. Substituents on position 4 included CH3, CO2H, CH2CO2H, CH = CHCO2H, and CH2CH2CO2H. The aromatic substituents included OH, OCH3, OCOCH3, CH2CH3, and Cl. Also included in the study were 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic, 2-oxo-2H-naphtho[1,2-b]pyran-4-acetic, and 1-naphthylacetic acids. The benzopyran and naphthopyran derivatives were prepared by the classical von Pechmann reaction. General structure-activity relationships reveal that optimal enzyme inhibitory activity is displayed by those compounds possessing the acetic acid moiety. For example, the most potent derivative, 3-oxo-3H-naphtho[2,1-b]pyran-1-acetic acid with an IC50 of 0.020 microM, is as potent as sorbinil (IC50 = 0.017 microM) in the crude rat lens aldose reductase assay.
• Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives
  作者：Mehul M. Patel、Mimansha D. Mali、Saurabh K. Patel

  DOI：10.1016/j.bmcl.2010.06.001

  日期：2010.11

  The condensation reaction of diphenylamine with 2-oxo-2H-(substituted chromen)-4-yl acetic acid in presence of anhydrous zinc chloride afford 4-(acridine-9-ylmethyl)-2H-(substituted chromen)-2-one. The synthesized compounds were characterized by spectral studies and elemental analysis and screened for their in vitro antibacterial activity against Staphylococcus aureus, Staphylococcus pyogenes (gram (+)ve), Escherichia coli, Pseudomonas aeruginosa (gram -ve) and antifungal activity against Aspergillus niger and anticancer activity (HL-60, Hep-2 & HEK293T) by MTT assay. Chloro substituted compounds showed antimicrobial and anticancer activity with IC50 values in the low micromolar range. (C) 2010 Published by Elsevier Ltd.
• Synthesis of coumarin based fluorescent compounds
  作者：Kailas K. Sanap、Shriniwas D. Samant

  DOI：10.1016/j.tetlet.2012.07.111

  日期：2012.10

  The reaction of different 7,8-disubstituted coumarin 4-acetic acids with 7-diethylaminocoumarin-3-carb-aldehyde in the presence of piperidine in methanol gives highly fluorescent (E)-1-(7-diethylaminocoumarin-3-yl)-2-(7,8-disubstituted coumarin-4-yl)ethenes in good yield. Only the (E) diastereomers of these are obtained. The compounds are new, orange to red in colour and show emission in yellow to red region. These compounds were further studied for their emission properties. (C) 2012 Elsevier Ltd. All rights reserved.
• SHRIDHAR D. R.; SASTRY C. V. R.; VAIDYA N. K.; MOORTY S. R.; REDDI G. S.;+, INDIAN. J. CHEM., 1978, B16, NO 8, 704-708
  作者：SHRIDHAR D. R.、 SASTRY C. V. R.、 VAIDYA N. K.、 MOORTY S. R.、 REDDI G. S.、+

  DOI：——

  日期：——