(S)-[(R)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol | 194539-34-9

• 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)-[(R)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol
• CAS: 194539-34-9
• 化学式: C₁₅H₁₃N₃O₅
• 分子量: 315.285
• InChiKey: MVSKQNXMMDYWQU-YSPPHNQVSA-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：

  (S)-[(R)-1-(2,4-Dinitro-phenyl)-aziridin-2-yl]-phenyl-methanol 在 氢氧化钾 、 sodium hydroxide 、 Amberlite IRA-400 (OH^-) resin 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 正丁醇 为溶剂， 反应 14.0h， 生成 Decanoic acid {(1R,2S)-2-hydroxy-2-phenyl-1-[((1R,2S,3S,4R,5R)-2,3,4-trihydroxy-5-hydroxymethyl-cyclohexylamino)-methyl]-ethyl}-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：

  (1S,2R)-2-(2,4-Dinitro-phenylamino)-1-phenyl-propane-1,3-diol 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 (S)-[(R)-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