(3S,4S)-4-azido-3-hydroxy-6-phenylhexanoic acid | 125218-44-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,4S)-4-azido-3-hydroxy-6-phenylhexanoic acid
• CAS: 125218-44-2
• 化学式: C₁₂H₁₅N₃O₃
• 分子量: 249.269
• InChiKey: LLENGMMZAGCPSI-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106.29
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-azido-3-hydroxy-6-phenylhexanoic acid 在 水 、 N,N-二异丙基乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Design and Synthesis of Potent Inhibitors of the Malaria Aspartyl Proteases Plasmepsin I and II. Use of Solid-Phase Synthesis to Explore Novel Statine Motifs

  摘要：

  Picomolar to low nanomolar inhibitors of the two aspartic proteases plasmepsin (Plm) I and II, from the malaria parasite Plasmodium falciparum, have been identified from sets of libraries containing novel statine-like templates modified at the amino and carboxy terminus. The syntheses of the novel statine templates were carried out in solution phase using efficient synthetic routes and resulting in excellent stereochemical control. The most promising statine template was attached to solid support and diversified by use of parallel synthesis. The products were evaluated for their Plm I and II inhibitory activity as well as their selectivity over cathepsin D. Selected inhibitors were, in addition, evaluated for their inhibition of parasite growth in cultured infected human red blood cells. The most potent inhibitor in this report, compound 16, displays K-i values of 0.5 and 2.2 nM for Plm I and II, respectively. Inhibitor 16 is also effective in attenuating parasite growth in red blood cells showing 51% inhibition at a concentration of 5 muM. Several inhibitors have been identified that exhibit K-i values between 0.5 and 74 nM for both Plm I and II. Some of these inhibitors also show excellent selectivity vs cathepsin D.

  DOI：

  10.1021/jm031106i
• 作为产物：
  描述：

  (3aR,5S,6aR)-2,2-dimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole 在 sodium hydroxide 、 potassium permanganate 、 sodium periodate 、 copper(l) iodide 、 sodium azide 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 48.5h， 生成 (3S,4S)-4-azido-3-hydroxy-6-phenylhexanoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of Pyrrolydinonyl Thymine Nucleoside Analogues

  摘要：

  描述了从天然苹果酸出发，实现一类新型光学活性核苷类似物的对映选择性合成。在所给的核苷类似物中，四氢呋喃环被一个带有伯醇和仲醇的吡咯烷酮环取代，这可能对制备新型寡核苷酸有用。经测试，制备的核苷类似物对病毒没有活性。

  DOI：

  10.1246/cl.1999.687

文献信息

• YANAGISAWA, HIROAKI;KANAZAKI, TAKURO;NISHI, TAKAHIDE, CHEM. LETT.,(1989) N, C. 687-690
  作者：YANAGISAWA, HIROAKI、KANAZAKI, TAKURO、NISHI, TAKAHIDE

  DOI：——

  日期：——