2-(4-(4-fluorobutyl)phenyl methyl)thio 3-methyl chromen-4-one | 868731-70-8

• 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-(4-(4-fluorobutyl)phenyl methyl)thio 3-methyl chromen-4-one
• 英文别名: 2-(4-(4-fluorobutyl)phenylmethyl)thio-3-methyl chromen-4-one；2-[[[4-(4-Fluorobutyl)phenyl]methyl]thio]-3-methyl-4H-1-benzopyran-4-one；2-[[4-(4-fluorobutyl)phenyl]methylsulfanyl]-3-methylchromen-4-one
• CAS: 868731-70-8
• 化学式: C₂₁H₂₁FO₂S
• 分子量: 356.461
• InChiKey: FSZGSKABPZYZBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(4-fluorobutyl)phenyl methyl)thio 3-methyl chromen-4-one 、 1-溴-2-氟乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以6%的产率得到2-[[4-[4-(2-Fluoroethoxy)butyl]phenyl]methylsulfanyl]-3-methylchromen-4-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm0701831
• 作为产物：
  描述：

  toluene-4-sulfonic acid 4-[4-(3-methyl-4-oxo-4H-chromen-2-ylsulfanylmethyl)-phenyl]-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(4-(4-fluorobutyl)phenyl methyl)thio 3-methyl chromen-4-one
  参考文献：
  名称：

  Contrast agents for myocardial perfusion imaging

  摘要：

  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。

  公开号：

  US20050244332A1

文献信息

• COMPOSITIONS, METHODS, AND SYSTEMS FOR THE SYNTHESIS AND USE OF IMAGING AGENTS
  申请人：Lantheus Medical Imaging, Inc.

  公开号：US20150196672A1

  公开（公告）日：2015-07-16

  The present invention provides compounds with imaging moieties for imaging a subject. The present invention also relates to systems, compositions, and methods for the synthesis and use of imaging agents, or precursors thereof. An imaging agent precursor may be converted to an imaging agent using the methods described herein. In some cases, a composition or plurality of imaging agents is enriched in 18 F. In some cases, an imaging agent may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs.

  本发明提供了具有成像基团的化合物，用于对受试者进行成像。本发明还涉及用于合成和使用成像试剂或其前体的系统、组合物和方法。成像试剂前体可以使用本文所述的方法转化为成像试剂。在某些情况下，组合物或多种成像试剂富集于 18 F。在某些情况下，成像试剂可用于成像受试者的感兴趣区域，包括但不限于心脏、心血管系统、心脏血管、大脑和其他器官。
• 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。
• APPARATUS FOR SYNTHESIZING THE IMAGING AGENT 4-CHLORO-2-(1,1-DIMETHYLETHYL)-5-[[4-[[2-(FLUORO-[18F])ETHOXY]METHYL]PHENYL]METHOXY]-3(2H)-PYRIDAZINONE (FLUORPIRIDAZ [18F])
  申请人：Lantheus Medical Imaging, Inc.

  公开号：EP3653621A1

  公开（公告）日：2020-05-20

  An apparatus for synthesizing the imaging agent of the formula comprising a cassette as shown in Figure 17 with a linear arrangement of a plurality of stopcock manifolds arranged in the order: 1) luer connections to gas inlet and [18O]H2O recovery; 2) anion exchange cartridge - column eluting solution; 3) spike connection for acetonitrile; 4) empty syringe; 5) reservoir with solution of imaging agent precursor; 6) reaction vessel; 7) outlet to HPLC; 8) syringe with solution of a stabilizing agent; 9) inlet from HPLC; 10) ethanol reservoir; 11) syringe with solution of a stabilizing agent; 12) syringe with water; 13) final product vial; 14) empty syringe; and 15) reaction vessel and exhaust; further comprising tubing, an imaging agent synthesis module, wherein the apparatus is fluidically connected to the apparatus, and wherein the solution of a stabilizing agent comprises a solution comprising ascorbic acid or a salt thereof.

  一种合成式中成像剂的装置 包括一个如图 17 所示的盒体，盒体上直线排列着多个按顺序排列的截止阀歧管： 1）气体入口和[18O]H2O 回收的鲁尔接头； 2) 阴离子交换滤芯-柱洗脱液； 3) 用于乙腈的尖头连接； 4) 空注射器 5) 装有成像剂前体溶液的容器； 6) 反应容器 7) 连接 HPLC 的出口； 8) 装有稳定剂溶液的注射器； 9) 高效液相色谱仪的入口 10）乙醇储液器 11) 装有稳定剂溶液的注射器； 12) 装有水的注射器 13) 最终产品小瓶 14) 空注射器；以及 15) 反应容器和排气管； 进一步包括管道、成像剂合成模块，其中该装置与该设备流体连接，稳定剂溶液包括由抗坏血酸或其盐组成的溶液。
• Compositions, methods, and systems for the synthesis and use of imaging agents
  申请人：Lantheus Medical Imaging, Inc.

  公开号：US10500293B2

  公开（公告）日：2019-12-10

  The present invention provides compounds with imaging moieties for imaging a subject. The present invention also relates to systems, compositions, and methods for the synthesis and use of imaging agents, or precursors thereof. An imaging agent precursor may be converted to an imaging agent using the methods described herein. In some cases, a composition or plurality of imaging agents is enriched in 18F. In some cases, an imaging agent may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs.

  本发明提供了具有成像分子的化合物，用于对主体成像。本发明还涉及成像剂或其前体的合成和使用系统、组合物和方法。成像剂前体可通过本文所述方法转化为成像剂。在某些情况下，成像剂组合物或多种成像剂富含 18F。在某些情况下，成像剂可用于成像受试者感兴趣的区域，包括但不限于心脏、心血管系统、心脏血管、大脑和其他器官。