(R)-[(S)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol | 194539-35-0

• 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: (R)-[(S)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol
• CAS: 194539-35-0
• 化学式: C₁₅H₁₃N₃O₅
• 分子量: 315.285
• InChiKey: MVSKQNXMMDYWQU-QMRHZFGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  109.52
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-[(S)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol 在 sodium hydroxide 、 Amberlite IRA-400 (OH^-) resin 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 76.0h， 生成 Decanoic acid ((2S,3R)-2-decanoylamino-3-hydroxy-3-phenyl-propyl)-((1R,4R,5S,6S)-4,5,6-trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-amide
  参考文献：
  名称：

  Synthesis and biological evaluation of four stereoisomers of PDMP-analogue, N-(2-decylamino-3-hydroxy-3-phenylprop-1-yl)-β-valienamine, and related compounds

  摘要：

  All stereoisomers with regard to C-1 and 2 of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) analogue containing unsaturated (beta-valienamine) and saturated 5a-carba-beta-D-glucopyranosylamine (beta-validamine) residues in place of morpholine moiety were synthesized. Although PDMP is a potent and specific glucosylceramide synthase inhibitor, the former valienamine analogues (4a-d) have been shown to be strong glucocerebrosidase inhibitors (IC50 3-7 x 10(-7) M). The latter validamine analogues (5a-d) were also moderate glucocerebrosidase inhibitors (IC50 5-20 x 10(-6) M). A series of compounds synthesized lacked an inhibitory potency against the glucosyltransferase at all. Whereas the analogue 6a composed of epimeric alpha-valienamine residue did not possess any potency against both enzymes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00341-7
• 作为产物：
  描述：

  (1R,2S)-(+)-2-amino-1-phenyl-1,3-propanediol 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 生成 (R)-[(S)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol
  参考文献：
  名称：

  Synthesis and biological evaluation of four stereoisomers of PDMP-analogue, N-(2-decylamino-3-hydroxy-3-phenylprop-1-yl)-β-valienamine, and related compounds

  摘要：

  All stereoisomers with regard to C-1 and 2 of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) analogue containing unsaturated (beta-valienamine) and saturated 5a-carba-beta-D-glucopyranosylamine (beta-validamine) residues in place of morpholine moiety were synthesized. Although PDMP is a potent and specific glucosylceramide synthase inhibitor, the former valienamine analogues (4a-d) have been shown to be strong glucocerebrosidase inhibitors (IC50 3-7 x 10(-7) M). The latter validamine analogues (5a-d) were also moderate glucocerebrosidase inhibitors (IC50 5-20 x 10(-6) M). A series of compounds synthesized lacked an inhibitory potency against the glucosyltransferase at all. Whereas the analogue 6a composed of epimeric alpha-valienamine residue did not possess any potency against both enzymes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00341-7