(2S)-3-bromo-2-hydroxy-2-methylpropanoyl chloride | 1010729-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-3-bromo-2-hydroxy-2-methylpropanoyl chloride
• CAS: 1010729-05-1
• 化学式: C₄H₆BrClO₂
• 分子量: 201.447
• InChiKey: DEXFBFYVUNWNKF-SCSAIBSYSA-N

物化性质

• 沸点：
  224.9±30.0 °C(Predicted)
• 密度：
  1.770±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-3-bromo-2-hydroxy-2-methylpropanoyl chloride 、 4-氨基-2-三氟甲基苯甲腈 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 以86%的产率得到(2S)-3-溴-N-[4-氰基-3-(三氟甲基)苯基]-2-羟基-2-甲基-丙酰胺
  参考文献：
  名称：

  Synthesis and biological activity of ferrocenyl derivatives of the non-steroidal antiandrogens flutamide and bicalutamide

  摘要：

  A series of ferrocenyl derivatives of the two non steroidal antiandrogens flutamide and bicalutamide have been prepared. Ferrocenyl bicalutamide complexes were initially synthesized in their racemic forms, and subsequently prepared as pure (R) and (S) enantiomers, and their structure was determined by X-ray crystallography. Most of the complexes retain a modest affinity for the androgen receptor and show an antiproliferative effect on both hormone-dependent (LNCaP) and -independent (PC-3) prostate cancer cells. Ferrocenyl derivatives of bicalutamide are the most cytotoxic (IC50 values on PC-3 around 15 mu M); however, they are less potent than the ferrocenyl derivatives of ethynyltestosterone or nilutamide (IC50 around 5 mu M). (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.051
• 作为产物：
  描述：

  (2S)-3-溴-2-羟基-2-甲基丙酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2S)-3-bromo-2-hydroxy-2-methylpropanoyl chloride
  参考文献：
  名称：

  [EN] A METHOD OF TREATING ANDROGEN RECEPTOR (AR)-POSITIVE BREAST CANCERS WITH SELECTIVE ANDROGEN RECEPTOR MODULATOR (SARMS)
  [FR] MÉTHODE DE TRAITEMENT DU CANCER DU SEIN POSITIF AUX RÉCEPTEURS ANDROGÈNES (AR+) AVEC MODULATEUR SÉLECTIF DES RÉCEPTEURS ANDROGÈNES (SARM)

  摘要：

  公开号：

  WO2014011220A3

文献信息

• [EN] A METHOD OF TREATING ANDROGEN RECEPTOR (AR)-POSITIVE BREAST CANCERS WITH SELECTIVE ANDROGEN RECEPTOR MODULATOR (SARMS)<br/>[FR] MÉTHODE DE TRAITEMENT DU CANCER DU SEIN POSITIF AUX RÉCEPTEURS ANDROGÈNES (AR+) AVEC MODULATEUR SÉLECTIF DES RÉCEPTEURS ANDROGÈNES (SARM)
  申请人：GTX INC

  公开号：WO2014011220A3

  公开（公告）日：2015-03-05
• Synthesis and biological activity of ferrocenyl derivatives of the non-steroidal antiandrogens flutamide and bicalutamide
  作者：Olivier Payen、Siden Top、Anne Vessières、Emilie Brulé、Agnès Lauzier、Marie-Aude Plamont、Michael J. McGlinchey、Helge Müller-Bunz、Gérard Jaouen

  DOI：10.1016/j.jorganchem.2010.10.051

  日期：2011.3

  A series of ferrocenyl derivatives of the two non steroidal antiandrogens flutamide and bicalutamide have been prepared. Ferrocenyl bicalutamide complexes were initially synthesized in their racemic forms, and subsequently prepared as pure (R) and (S) enantiomers, and their structure was determined by X-ray crystallography. Most of the complexes retain a modest affinity for the androgen receptor and show an antiproliferative effect on both hormone-dependent (LNCaP) and -independent (PC-3) prostate cancer cells. Ferrocenyl derivatives of bicalutamide are the most cytotoxic (IC50 values on PC-3 around 15 mu M); however, they are less potent than the ferrocenyl derivatives of ethynyltestosterone or nilutamide (IC50 around 5 mu M). (C) 2010 Elsevier B. V. All rights reserved.