ethyl 6-methoxy-4-oxo-4H-chromene-2-carboxylate | 52866-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 6-methoxy-4-oxo-4H-chromene-2-carboxylate
• 英文别名: ethyl 6-methoxy-4-oxochromene-2-carboxylate
• CAS: 52866-24-7
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: KZRZAAXSMNRRHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-methoxy-4-oxo-4H-chromene-2-carboxylate 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.17h， 生成 {3-[(6-methoxy-4-oxo-4H-chromene-2-ylcarbonyl)amino]propyl}trimethylammonium iodide
  参考文献：
  名称：

  Chromone derivatives which bind to human hair

  摘要：

  Chromone derivatives bearing a quaternary ammonium functionality which bind to human hair were synthesised. The radical scavenging activity, according to the DPPH assay, of the chromone derivatives is considerably lower compared with flavonoids. The compounds show interesting UV absorption properties that depend on the position of a methoxy substituent. A bathochromic shift of 29 nm was observed when the methoxy group on the ammonium salts were shifted from position 7 to position 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.081
• 作为产物：
  描述：

  在 polyphosphoric acid 作用下， 以 neat (no solvent) 为溶剂， 生成 ethyl 6-methoxy-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  An Efficient Construction of 4-Oxo-4H-chromene-2-carboxylate Derivatives via One-Pot Cascade Reaction Under Solvent-Free Conditions

  摘要：

  An efficient synthetic strategy to chromone derivatives from commercially available diethyl acetylenedicarboxylate and phenols via a one-pot cascade reaction has been developed. Performing the reaction using pyridine and polyphosphoric acid as the catalyst at room temperature and 90 degrees C without any solvent gave the chromone derivatives in good to high yields at one time. A possible reaction pathway was also proposed and supported by the experiment. This protocol is environmentally friendly and metal-free, with advantages including short reaction times, convenient operation, and mild reaction conditions.

  DOI：

  10.3987/com-15-13191

文献信息

• [EN] SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY<br/>[FR] CYCLOLALKYLES SUBSTITUÉS EN TANT QUE MODULATEURS DE LA VOIE DE STRESS INTÉGRÉE
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2020223536A1

  公开（公告）日：2020-11-05

  Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

  本文提供了用于调节综合应激反应（ISR）并治疗相关疾病、疾病和症状的化合物、组合物和方法。
• [EN] ANTI-INFECTIVE AGENTS<br/>[FR] AGENTS ANTI-INFECTIEUX
  申请人：UNIV DUNDEE

  公开号：WO2017221002A1

  公开（公告）日：2017-12-28

  The present invention relates to a novel class of chromene-2-carboxamide compounds inhibitors of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and their use as anti-infective agents in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

  本发明涉及一类新型的基于色酮-2-羧酰胺化合物的抑制剂，其通式为(I)，其中R1、R2、R3、R4、R5、R6、R7、R8和X如本文所定义，其在医学上的用途，特别是作为抗感染剂的用途，包括含有它们的组合物，其制备过程以及用于这些过程的中间体。
• Design and synthesis of chromone-based monoamine oxidase B inhibitors with improved drug-like properties
  作者：Joana Reis、Carlos Fernandes、Hoda Salem、Marta Maia、Cláudia Tomé、Sofia Benfeito、José Teixeira、Paulo J. Oliveira、Eugenio Uriarte、Francesco Ortuso、Stefano Alcaro、Donatella Bagetta、Fernando Cagide、Fernanda Borges

  DOI：10.1016/j.ejmech.2022.114507

  日期：2022.9

  reversible inhibitors targeting MAO-B is still a desirable line of therapeutic research. Within this framework, a small library of chromone derivatives was synthesized and screened towards human monoamine oxidases. Structural modifications on the chromone 3-phenylcarboxamide resulted in potent MAO-B inhibitors with an improved drug-like profile, and for the first time we obtained potent and selective chromone

  帕金森病治疗中缺乏改善疾病的药物促使新的化学实体作用于相关的 PD 相关生物靶点。因此，开发靶向 MAO-B 的选择性和可逆抑制剂仍然是治疗研究的理想方向。在这个框架内，合成了一个小的色酮衍生物库，并针对人类单胺氧化酶进行了筛选。色酮 3-苯基甲酰胺的结构修饰产生了有效的 MAO-B 抑制剂，具有改善的药物样特性，并且我们首次获得了在低纳摩尔范围内起作用的强效和选择性色酮 2-苯基甲酰胺。化合物 5-hydroxy-4-oxo- N -phenyl-4H-chromene-3-carboxamide ( 38 ) (IC 50  = 13.0 nM) 和N-(4-chlorophenyl)-5-hydroxy-4-oxo-4H-chromene-3-carboxamide ( 41 ) (IC 50  = 8.3 nM) 作为可逆、有效、选择性和非细胞毒性 MAO-B 抑制剂脱颖而出有利的药物样配置文件。两种化合物都显示出对铁
• 一种色酮-2-甲酰胺类化合物用于制备降血糖药物的用途及其制备方法
  申请人：广西民族大学

  公开号：CN115536644A

  公开（公告）日：2022-12-30

  本发明公开了一种色酮‑2‑甲酰胺类化合物用于制备降血糖药物的用途，该色酮‑2‑甲酰胺类化合物为以下任意一种：7‑甲氧基‑4‑氧代‑N‑(吡啶‑3‑基)‑4H‑色烯‑2‑甲酰胺、6‑甲氧基‑4‑氧代‑N‑(吡啶‑3‑基)‑4H‑色烯‑2‑甲酰胺、6‑氟‑4‑氧代‑N‑(吡啶‑3‑基)‑4H‑色烯‑2‑甲酰胺、6‑溴‑4‑氧代‑N‑(吡啶‑3‑基)‑4H‑色烯‑2‑甲酰胺。本发明还公开了该色酮‑2‑甲酰胺类化合物的制备方法。本发明的化合物具有较好的降糖作用，同时能够避免不良副作用，有望代替现有技术中PPARγ全激动剂，提高用药安全性。
• Sagorewskii et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1026,1029; engl. Ausg. S. 1004, 1006
  作者：Sagorewskii et al.

  DOI：——

  日期：——