(E)-3-(1-((3S,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide

• 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: (E)-3-(1-((3S,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide
• 英文别名: (E)-3-[1-[(3S,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidin-3-yl]triazol-4-yl]-N-hydroxyprop-2-enamide
• 化学式: C₁₇H₂₁N₅O₃
• 分子量: 343.385
• InChiKey: HQAPXTJDDNHIDZ-MIVXPEEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,4R)-1-benzyl-4-hydroxyproline methyl ester 在 sodium tetrahydroborate 、 triethylphosphite copper(I) iodide complex 、 三异丙基硅烷 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 35.5h， 生成 (E)-3-(1-((3S,5S)-1-benzyl-5-(hydroxymethyl)pyrrolidin-3-yl)-1H-1,2,3-triazol-4-yl)-N-hydroxyacrylamide
  参考文献：
  名称：

  A sub-milligram-synthesis protocol for in vitro screening of HDAC11 inhibitors

  摘要：

  This work demonstrated the high efficiency of a sub-milligram-synthesis based medicinal chemistry method. Totally 72 compounds, consisting a tri-substituted pyrrolidine core, were prepared. Around 0.1 mg of each compound was solid-phase synthesized. Based on the additive property of UV absorptions of unconjugated chromophores of a molecule, these compounds were quantified by UV measurement. A hit, whose IC50 value was 1.2 mu M in HDAC11 inhibition assays, highlights the applicability of the approach reported here in future optimization works. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.03.116

文献信息

• A sub-milligram-synthesis protocol for in vitro screening of HDAC11 inhibitors
  作者：Yinping Tian、Jin Jin、Congying Wang、Wenhui Lv、Xuewei Li、Xiaona Che、Yanchao Gong、Yanjun Li、Quanli Li、Jingli Hou、Peng G. Wang、Jie Shen

  DOI：10.1016/j.bmcl.2016.03.116

  日期：2016.5

  This work demonstrated the high efficiency of a sub-milligram-synthesis based medicinal chemistry method. Totally 72 compounds, consisting a tri-substituted pyrrolidine core, were prepared. Around 0.1 mg of each compound was solid-phase synthesized. Based on the additive property of UV absorptions of unconjugated chromophores of a molecule, these compounds were quantified by UV measurement. A hit, whose IC50 value was 1.2 mu M in HDAC11 inhibition assays, highlights the applicability of the approach reported here in future optimization works. (C) 2016 Published by Elsevier Ltd.