2-methanesulfinyl-3-methylchromen-4-one | 668462-24-6

• 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: 2-methanesulfinyl-3-methylchromen-4-one
• 英文别名: 2-methanesulfinyl-3-methyl-chromen-4-one；3-methyl-2-methylsulfinylchromen-4-one
• CAS: 668462-24-6
• 化学式: C₁₁H₁₀O₃S
• 分子量: 222.265
• InChiKey: CPWDXCHXWXOCJA-UHFFFAOYSA-N

物化性质

• 沸点：
  396.8±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-叔丁基苯乙胺 、 2-methanesulfinyl-3-methylchromen-4-one 以 乙腈 为溶剂， 反应 24.0h， 生成 2-[2-(4-Tert-butylphenyl)ethylamino]-3-methylchromen-4-one
  参考文献：
  名称：

  The design and synthesis of novel inhibitors of NADH:ubiquinone oxidoreductase

  摘要：

  Potent new inhibitors of NADH:ubiquinone oxidoreductase (complex 1) have been designed, with the help of molecular modelling, by hybridisation of known complex I inhibitors with inhibitors of cytochrome c oxidoreductase. The most interesting compound was the chromone 7 which was a selective inhibitor of complex I (IC50 15 nM) and showed acaricidal activity against spider mites. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.022
• 作为产物：
  描述：

  2-thio-3-methyl chromen-4-one 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 36.0h， 生成 2-methanesulfinyl-3-methylchromen-4-one
  参考文献：
  名称：

  The design and synthesis of novel inhibitors of NADH:ubiquinone oxidoreductase

  摘要：

  Potent new inhibitors of NADH:ubiquinone oxidoreductase (complex 1) have been designed, with the help of molecular modelling, by hybridisation of known complex I inhibitors with inhibitors of cytochrome c oxidoreductase. The most interesting compound was the chromone 7 which was a selective inhibitor of complex I (IC50 15 nM) and showed acaricidal activity against spider mites. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.022

文献信息

• Contrast agents for myocardial perfusion imaging
  申请人：Radeke S. Heike

  公开号：US20050244332A1

  公开（公告）日：2005-11-03

  The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

  本公开涉及部分用于心肌灌注成像的化合物和方法，包括向患者注射一种对MC-1结合的化合物和成像基团构成的造影剂，并利用诊断成像对患者进行扫描。
• CONTRAST AGENTS FOR MYOCARDIAL PERFUSION IMAGING
  申请人：Radeke Heike S.

  公开号：US20090104118A1

  公开（公告）日：2009-04-23

  The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

  本公开涉及部分化合物和成像心肌灌注的方法，包括向患者注射一种对MC-1具有结合作用的化合物和成像基团构成的对比剂，并使用诊断成像对患者进行扫描。
• Synthesis and Biological Evaluation of the Mitochondrial Complex 1 Inhibitor 2-[4-(4-Fluorobutyl)benzylsulfanyl]-3-methylchromene-4-one as a Potential Cardiac Positron Emission Tomography Tracer
  作者：Heike Radeke、Kelley Hanson、Padmaja Yalamanchili、Megan Hayes、Zhi-Qin Zhang、Michael Azure、Ming Yu、Mary Guaraldi、Mikhail Kagan、Simon Robinson、David Casebier

  DOI：10.1021/jm0701831

  日期：2007.9.1

  A series of fluorinated chromone analogs with IC50 values ranging from 9 to 133 nM for the mitochondrial complex I (MC-I) has been prepared. A structure -activity relationship (SAR) study of the most potent fluorinated chromone analog 10 demonstrated the linkage heteroatom preference of the side chain region of the molecule while maintaining potent MC-I inhibitory activity. Tissue distribution studies 30 min after [F-18]10 administration to Sprague-Dawley (SD) rats demonstrated high uptake of the radiotracer from the blood pool into the myocardium (2.24% ID/g), kidney (1.93% ID/g), and liver (2.00% ID/g). After 2 h about 66% of the activity in the myocardiurn at 30 min had been retained, whereas -70% had been cleared from the liver and kidney. MicroPET images of SD rats after [F-18]10 administration allowed easy assessment of the myocardium through 60 min with minimal lung or liver interference.
• EP1740225A4
  申请人：——

  公开号：EP1740225A4

  公开（公告）日：2009-08-19
• Contrast Agents for Myocardial Perfusion Imaging
  申请人：Lantheus Medical Imaging, Inc.

  公开号：EP2253333B1

  公开（公告）日：2019-06-12