(1S,2R)-2-amino-1-(4-fluorophenyl)propanol | 502850-06-8

• 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: (1S,2R)-2-amino-1-(4-fluorophenyl)propanol
• 英文别名: (1S,2R)-2-amino-1-(4-fluorophenyl)propan-1-ol
• CAS: 502850-06-8
• 化学式: C₉H₁₂FNO
• 分子量: 169.199
• InChiKey: NFIUKBOGCIKNNF-HZGVNTEJSA-N

物化性质

• 沸点：
  292.0±25.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-amino-1-(4-fluorophenyl)propanol 在 氯化亚砜 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 42.0h， 生成 (2S,3R)-2-(4-氟苯基)-3-甲基氮丙啶
  参考文献：
  名称：

  Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

  摘要：

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.079
• 作为产物：
  描述：

  (R)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanone 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 12.5h， 生成 (1S,2R)-2-amino-1-(4-fluorophenyl)propanol
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes

  摘要：

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.

  DOI：

  10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q

文献信息

• Design, synthesis of auristatins-glucuronide conjugates targeting the β-glucuronidase in tumor microenvironment
  作者：Yujie Wang、Keshi Xu、Hongchun Liu、Wei Zhang、Chun Hu、Yingxia Li

  DOI：10.1016/j.bmcl.2023.129493

  日期：2023.10

  Auristatins-glucuronide conjugates designed targeting the β-Glucuronidase in tumor microenvironment were synthesized and evaluated on stabilities, the release of auristatins and the antitumor activities in this study. Conjugates 20 and 21 showed remarkable stabilities in phosphate buffer and bovine serum solution, and excellent selectivity between the in vitro antiproliferative activities against β-glucuronidase

  在本研究中，合成了针对肿瘤微环境中的β-葡萄糖醛酸酶的Auristatins-葡萄糖醛酸苷缀合物，并对其稳定性、auristatins的释放和抗肿瘤活性进行了评估。缀合物20和21在磷酸盐缓冲液和牛血清溶液中表现出显着的稳定性，并且在针对 β-葡萄糖醛酸酶预处理和未处理的癌细胞的体外抗增殖活性之间具有优异的选择性（IC 50  = 5.7 nM ∼ 9.7 nM，IC 50 (-Enz) > 1μM）。此外，缀合物20在 HCT-116 异种移植小鼠模型中显示出有效的抗肿瘤功效，且不会引起副作用。
• Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds
  作者：Gilles Berger、Michel Gelbcke、Emilie Cauët、Michel Luhmer、Jean Nève、François Dufrasne

  DOI：10.1016/j.tetlet.2012.11.079

  日期：2013.2

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes
  作者：Francois Dufrasne、Michael Gelbcke、Beate Schnurr、Ronald Gust

  DOI：10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q

  日期：2002.5

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.