(1R,2S)-1,2-diamino-1-(4-fluorophenyl)propane | 502850-17-1

• 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: (1R,2S)-1,2-diamino-1-(4-fluorophenyl)propane
• 英文别名: (1R,2S)-1-(4-fluorophenyl)propane-1,2-diamine
• CAS: 502850-17-1
• 化学式: C₉H₁₃FN₂
• 分子量: 168.214
• InChiKey: DLHWAMGLQXPUOE-RCOVLWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  52
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  桃金娘烯醛 、 (1R,2S)-1,2-diamino-1-(4-fluorophenyl)propane 以 氘代氯仿 为溶剂， 反应 48.0h， 生成 (1R,2S)-N²-[1-((1R,5S)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-meth-(E)-ylidene]-1-(4-fluoro-phenyl)-propane-1,2-diamine
  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
• 作为产物：
  描述：

  (1RS,2S)-N-carbethoxy-2-amino-1-(4-fluorophenyl)propanol 在 盐酸 、 氢氧化钾 作用下， 以 吡啶 、 甲醇 、 水 、 甲苯 为溶剂， 反应 64.0h， 生成 (1R,2S)-1,2-diamino-1-(4-fluorophenyl)propane
  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

• 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.