Methanesulfonic acid (2S,3S)-2-(2,4-dinitro-phenylamino)-3-hydroxy-3-phenyl-propyl ester | 194539-31-6

• 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: Methanesulfonic acid (2S,3S)-2-(2,4-dinitro-phenylamino)-3-hydroxy-3-phenyl-propyl ester
• CAS: 194539-31-6
• 化学式: C₁₆H₁₇N₃O₈S
• 分子量: 411.392
• InChiKey: NXTTZSHWMHIGCP-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  161.91
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2S,3S)-2-(2,4-dinitro-phenylamino)-3-hydroxy-3-phenyl-propyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 72.0h， 生成 (1S,2S)-2-(2,4-Dinitro-phenylamino)-1-phenyl-3-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-propan-1-ol
  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,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 吡啶 作用下， 生成 Methanesulfonic acid (2S,3S)-2-(2,4-dinitro-phenylamino)-3-hydroxy-3-phenyl-propyl ester
  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