6-chlorocoumarin-3-carboxylic acid | 72973-49-0

• 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: 6-chlorocoumarin-3-carboxylic acid
• 英文别名: 6-chloro-2-oxo-2H-chromene-3-carbonyl chloride；6-chloro-2-oxochromene-3-carbonyl chloride
• CAS: 72973-49-0
• 化学式: C₁₀H₄Cl₂O₃
• mdl: MFCD12197772
• 分子量: 243.046
• InChiKey: RLMRYRFPMMGSAT-UHFFFAOYSA-N

物化性质

• 沸点：
  407.6±45.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  6-chlorocoumarin-3-carboxylic acid 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 96.0h， 生成 4-[(6-Chloro-2-oxochromene-3-carbonyl)amino]benzoic acid
  参考文献：
  名称：

  一类新型的选择性抗幽门螺杆菌药物2-oxo-2H-chromne-3-羧酰胺衍生物。

  摘要：

  制备了一类新型的选择性抗幽门螺杆菌药物2-oxo-2H-苯甲基-3-羧酰胺衍生物，并对其抗菌活性进行了评估。所有合成的化合物对不同种类的革兰氏阳性细菌和革兰氏阴性细菌以及各种病原真菌菌株都几乎没有或没有活性。其中一些在0.0039-16 microg / mL MIC范围内对幽门螺杆菌的生长表现出有效而特异性的抑制作用，包括对甲硝唑具有抗性的菌株。还通过锥虫蓝染料排除试验对最具活性的化合物作为抗H进行了细胞毒性筛选。幽门螺杆菌制剂。在检查其细胞毒性潜力的衍生物中，许多衍生物诱导了低细胞毒性作用。

  DOI：

  10.1016/j.bmcl.2007.03.050
• 作为产物：
  描述：

  5-chloro-2-hydroxy-benzaldehyde oxime 在 sodium hydroxide 、 氯化亚砜 作用下， 生成 6-chlorocoumarin-3-carboxylic acid
  参考文献：
  名称：

  Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study

  摘要：

  A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, displaying pIC(50) values of particular interest: 2a shows pIC(50) 7.76 and a selectivity index (pS.I.) 2.94 and 2b shows pIC(50) 7.72 and a pS.I. of 2.80. The coumarin-3-acyl chlorides 3a-e showed high pIC(50) values against both MAO-A and MAO-B isoforms, 3d being the highest against MAO-B with a pIC(50) value of 8.00. In order to rationalize the activity/selectivity results, molecular descriptors were generated. Further insight about enzyme-inhibitor interaction was obtained by docking experiments with the MAO-B isoform. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.010

文献信息

• Design, synthesis and biological evaluation of coumarin derivatives as novel acetylcholinesterase inhibitors that attenuate H2O2-induced apoptosis in SH-SY5Y cells
  作者：Dahong Yao、Jing Wang、Guan Wang、Yingnan Jiang、Lei Shang、Yuqian Zhao、Jian Huang、Shilin Yang、Jinhui Wang、Yamei Yu

  DOI：10.1016/j.bioorg.2016.07.013

  日期：2016.10

  A novel series of coumarin derivatives were designed, synthesized and investigated for inhibition of cholinesterase, including acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE). This biological study showed that these compounds containing piperazine ring had significant inhibition activities on AChE rather than BuChE. Further study suggested that 9x, as one of this kind of structure derivative

  设计，合成和研究了一系列新的香豆素衍生物以抑制胆碱酯酶，包括乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）。这项生物学研究表明，这些含有哌嗪环的化合物对AChE而不是BuChE具有明显的抑制活性。进一步的研究表明，9x作为这种结构衍生物之一，对AChE表现出最强的抑制活性，IC 50值为34 nM。此外，分子对接，流式细胞术（FCM）和蛋白质印迹试验表明9x可以诱导细胞保护性自噬以减弱H 2 O 2。诱导的神经母细胞瘤SH-SY5Y细胞死亡。这些发现凸显了一种新的方法，可用于开发针对AChE的新型潜在神经保护化合物，该化合物在未来的阿尔茨海默氏病（AD）治疗中具有自噬诱导活性。
• Evaluation of novel<i>N</i>′-(3-hydroxybenzoyl)-2-oxo-2<i>H</i>-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors
  作者：Omobolanle J. Jesumoroti、Faridoon Faridoon、Dumisani Mnkandhla、Michelle Isaacs、Heinrich C. Hoppe、Rosalyn Klein

  DOI：10.1039/c8md00328a

  日期：——

  In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the

  为了确定对 HIV-1 IN 具有活性的潜在新药物，设计并合成了一系列新型香豆素-3-碳酰肼衍生物。这些化合物的毒性特征表明它们对人体细胞无毒，并且它们表现出有希望的抗 HIV-1 IN 活性，IC 50值在 nM 范围内。此外，一项伴随的分子建模研究表明，这些化合物与酶的活性口袋结合。
• Biological evaluation of coumarin derivatives as mushroom tyrosinase inhibitors
  作者：Jinbing Liu、Fengyan Wu、Lingjuan Chen、Liangzhong Zhao、Zibing Zhao、Min Wang、Sulan Lei

  DOI：10.1016/j.foodchem.2012.07.055

  日期：2012.12

  series of coumarin derivatives were synthesised and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesised compounds exhibited significant inhibitory activities. Especially, 2-(1-(coumarin-3-yl)ethylidene)hydrazinecarbothioamide bearing thiose-micarbazide group exhibited the most potent tyrosinase inhibitory activity

  合成了一系列香豆素衍生物，并评价了它们对蘑菇酪氨酸酶双酚酶活性的抑制作用。结果表明，某些合成的化合物表现出显着的抑制活性。尤其是带有巯基-氨基脲基的2-（1-（香豆素-3-基）亚乙基）肼甲硫代酰胺对IC 50的酪氨酸酶抑制作用最强。值为3.44μM。对2-（1-（香豆素-3-基）-亚乙基）肼甲硫代酰胺和2-（1-（6-氯香豆素-3-基）亚乙基）-肼甲硫代酰胺的抑制机理分析表明，该化合物对甲壳素具有抑制作用。酪氨酸酶是不可逆的。初步结构活性关系（SAR）分析表明，此类化合物的进一步开发可能会引起人们的兴趣。
• Synthesis and anticancer activities of some new coumarin derivatives including the triazole ring and their in silico molecular docking studies
  作者：Emre Menteşe、Adem Güner、Elifsu Polatlı、Mustafa Emirik、Hakan Bektaş、Bahittin Kahveci

  DOI：10.1002/ardp.202000284

  日期：2021.3

  The synthesis, docking study, and investigation of the anticancer activities of some coumarin derivatives containing the triazole ring are reported in this study. The newly synthesized compounds were screened for their in vitro anticancer activity against the cell lines CRL5807 (human bronchioalveolar carcinoma), CRL5826 (human squamous cell carcinoma), MDA-MB231 (human breast cancer cells), HTB177

  本研究报道了一些含有三唑环的香豆素衍生物的合成、对接研究和抗癌活性研究。筛选新合成的化合物对细胞系 CRL5807（人细支气管肺泡癌）、CRL5826（人鳞状细胞癌）、MDA-MB231（人乳腺癌细胞）、HTB177（人肺癌）、PC- 3（人前列腺腺癌）、PANC-1（人胰腺癌细胞）用作癌细胞，CCD34Lu（正常人肺成纤维细胞）用作健康细胞系。样品的细胞毒性作用通过 MTT（3-（4,5-二甲基-2-噻唑基）-2,5-二苯基-2H-溴化四唑）测定法测定。还进行了计算机研究以探索分子的结合相互作用。
• 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。