(S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide | 1337990-19-8

• 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: (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
• 英文别名: (2S)-N-[3-(Trifluoromethyl)-4-nitrophenyl]-2-methyl-2-hydroxy-3-(4-hydroxyphenoxy)propionamide；(2S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS: 1337990-19-8
• 化学式: C₁₇H₁₅F₃N₂O₆
• 分子量: 400.311
• InChiKey: FSAVDMVHDRRSMP-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide 、 [11C]methyl triflate 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 0.05h， 生成 (S)-2-hydroxy-3-(4-[11C]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Facile radiosynthesis of new carbon-11-labeled propanamide derivatives as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging

  摘要：

  The androgen receptor (AR) is an attractive target for the treatment and molecular imaging of prostate cancer. New carbon-11-labeled propanamide derivatives were first designed and synthesized as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging using the biomedical imaging technique positron emission tomography (PET). The target tracers, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methylpropanamide ([C-11]8a), (S)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8e), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-propanamide ([C-11]8c) and (S)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8g), were prepared by O-[C-11]methylation of their corresponding precursors, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methylpropanamide (9a), (S)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide (9b), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-propanamide (9c) and (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide (9d), with [C-11]CH3OTf under basic conditions and isolated by a simplified C-18 solid-phase extraction (SPE) method in 55 +/- 5% (n = 5) radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EDS) was 277.5 +/- 92.5 GBq/mu mol (n = 5). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.08.005
• 作为产物：
  描述：

  (S)-3-(4-(benzyloxy)phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide 在 二甲基硫 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到(S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Facile radiosynthesis of new carbon-11-labeled propanamide derivatives as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging

  摘要：

  The androgen receptor (AR) is an attractive target for the treatment and molecular imaging of prostate cancer. New carbon-11-labeled propanamide derivatives were first designed and synthesized as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging using the biomedical imaging technique positron emission tomography (PET). The target tracers, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methylpropanamide ([C-11]8a), (S)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8e), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-propanamide ([C-11]8c) and (S)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8g), were prepared by O-[C-11]methylation of their corresponding precursors, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methylpropanamide (9a), (S)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide (9b), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-propanamide (9c) and (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide (9d), with [C-11]CH3OTf under basic conditions and isolated by a simplified C-18 solid-phase extraction (SPE) method in 55 +/- 5% (n = 5) radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EDS) was 277.5 +/- 92.5 GBq/mu mol (n = 5). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.08.005

文献信息

• Facile radiosynthesis of new carbon-11-labeled propanamide derivatives as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging
  作者：Mingzhang Gao、Min Wang、Kathy D. Miller、Qi-Huang Zheng

  DOI：10.1016/j.steroids.2011.08.005

  日期：2011.12

  The androgen receptor (AR) is an attractive target for the treatment and molecular imaging of prostate cancer. New carbon-11-labeled propanamide derivatives were first designed and synthesized as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging using the biomedical imaging technique positron emission tomography (PET). The target tracers, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methylpropanamide ([C-11]8a), (S)-2-hydroxy-3-(2-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8e), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-propanamide ([C-11]8c) and (S)-2-hydroxy-3-(4-[C-11]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([C-11]8g), were prepared by O-[C-11]methylation of their corresponding precursors, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methylpropanamide (9a), (S)-2-hydroxy-3-(2-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide (9b), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-propanamide (9c) and (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide (9d), with [C-11]CH3OTf under basic conditions and isolated by a simplified C-18 solid-phase extraction (SPE) method in 55 +/- 5% (n = 5) radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EDS) was 277.5 +/- 92.5 GBq/mu mol (n = 5). (C) 2011 Elsevier Inc. All rights reserved.