(+/-)-3-fluoro-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide | 72114-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-3-fluoro-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
• 英文别名: 3-fluoro-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS: 72114-96-6
• 化学式: C₁₁H₁₀F₄N₂O₄
• 分子量: 310.205
• InChiKey: DOKFODCPWNEOMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-fluoro-2-hydroxy-2-methylpropanoyl chloride 、 5-氨基-2-硝基三氟甲苯 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以5.25 g的产率得到(+/-)-3-fluoro-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Prostate cancer PET bioprobes: Synthesis of [18F]-radiolabeled hydroxyflutamide derivatives

  摘要：

  Approximately 80-90% of prostate cancers are androgen dependent at initial diagnosis. The androgen receptor (AR) is present in most advanced prostate cancer specimens and is believed to have a critical role in its development. Today, treatment of prostate cancer is done by inhibition of AR using antiandrogens such as flutamide (pro-drug of hydroxyflutamide), nilutamide, and bicalutamide. However, there is currently no noninvasive imaging modalities to detect, guide, and monitor specific treatment of AR-positive prostate cancer. (R)-3-Bromo-N-(4-fluoro-3-(trifluoromethy, phenyl)-2-hydroxy-2-methyl-propanamide [F-18]-1 and N-(4fluoro-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide [F-18]-2, derivatives of hydroxyflutamide, were synthesized as a fluorine-containing imaging agent candidates. A three-step fluorine-18 radiosynthesis route was developed, and the compounds were successfully labeled with a 10 +/- 3% decay corrected radiochemical yield, 95% radiochemical purity, and a specific activity of 1500 +/- 200 Ci/mmol end of bombardment (n = 10). These labeled biprobes not only may enable for the future quantitative molecular imaging of AR-positive prostate cancer using positron emission tomography but may also allow for image-guided treatment of prostate cancer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.033

文献信息

• Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens
  作者：Jeffrey J. Morris、Leslie R. Hughes、Alasdair T. Glen、Peter J. Taylor

  DOI：10.1021/jm00105a067

  日期：1991.1

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.
• MORRIS, JEFFREY J.;HUGHES, LESLIE R.;GLEN, ALASDAIR T.;TAYLOR, PETER J., J. MED. CHEM., 34,(1991) N, C. 447-455
  作者：MORRIS, JEFFREY J.、HUGHES, LESLIE R.、GLEN, ALASDAIR T.、TAYLOR, PETER J.

  DOI：——

  日期：——
• Prostate cancer PET bioprobes: Synthesis of [18F]-radiolabeled hydroxyflutamide derivatives
  作者：Orit Jacobson、Yossi Bechor、Avi Icar、Nurit Novak、Atalia Birman、Hanit Marom、Ludmila Fadeeva、Elizabeth Golan、Ilan Leibovitch、Mordechai Gutman、Einat Even-Sapir、Roland Chisin、Michael Gozin、Eyal Mishani

  DOI：10.1016/j.bmc.2005.06.033

  日期：2005.11

  Approximately 80-90% of prostate cancers are androgen dependent at initial diagnosis. The androgen receptor (AR) is present in most advanced prostate cancer specimens and is believed to have a critical role in its development. Today, treatment of prostate cancer is done by inhibition of AR using antiandrogens such as flutamide (pro-drug of hydroxyflutamide), nilutamide, and bicalutamide. However, there is currently no noninvasive imaging modalities to detect, guide, and monitor specific treatment of AR-positive prostate cancer. (R)-3-Bromo-N-(4-fluoro-3-(trifluoromethy, phenyl)-2-hydroxy-2-methyl-propanamide [F-18]-1 and N-(4fluoro-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide [F-18]-2, derivatives of hydroxyflutamide, were synthesized as a fluorine-containing imaging agent candidates. A three-step fluorine-18 radiosynthesis route was developed, and the compounds were successfully labeled with a 10 +/- 3% decay corrected radiochemical yield, 95% radiochemical purity, and a specific activity of 1500 +/- 200 Ci/mmol end of bombardment (n = 10). These labeled biprobes not only may enable for the future quantitative molecular imaging of AR-positive prostate cancer using positron emission tomography but may also allow for image-guided treatment of prostate cancer. (c) 2005 Elsevier Ltd. All rights reserved.