methyl (2S)-4-methyl-2-(3-phenylprop-2-enoylamino)pentanoate | 87784-11-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-4-methyl-2-(3-phenylprop-2-enoylamino)pentanoate
• CAS: 87784-11-0
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: OXFYLVKTVPTJPQ-AWEZNQCLSA-N

物化性质

• 沸点：
  450.0±45.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-4-methyl-2-(3-phenylprop-2-enoylamino)pentanoate 在 sodium tetrahydroborate 、 水 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.83h， 生成
  参考文献：
  名称：

  α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment

  摘要：

  The main protease of coronaviruses and the 3C protease of enteroviruses share a similar active-site architecture and a unique requirement for glutamine in the P1 position of the substrate. Because of their unique specificity and essential role in viral polyprotein processing, these proteases are suitable targets for the development of antiviral drugs. In order to obtain near-equipotent, broad-spectrum antivirals against alphacoronaviruses, betacoronaviruses, and enteroviruses, we pursued a structure-based design of peptidomimetic alpha-ketoamides as inhibitors of main and 3C proteases. Six crystal structures of protease-inhibitor complexes were determined as part of this study. Compounds synthesized were tested against the recombinant proteases as well as in viral replicons and virus-infected cell cultures; most of them were not cell-toxic. Optimization of the P2 substituent of the alpha-ketoamides proved crucial for achieving near-equipotency against the three virus genera. The best near-equipotent inhibitors, 11u (P2 = cyclopentylmethyl) and 11r (P2 = cyclo-hexylmethyl), display low-micromolar EC50 values against enteroviruses, alphacoronaviruses, and betacoronaviruses in cell cultures. In Huh7 cells, 11r exhibits three-digit picomolar activity against the Middle East Respiratory Syndrome coronavirus.

  DOI：

  10.1021/acs.jmedchem.9b01828
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 、 肉桂酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 methyl (2S)-4-methyl-2-(3-phenylprop-2-enoylamino)pentanoate
  参考文献：
  名称：

  Wei; Jiang; Zhang, Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2383 - 2388

  摘要：

  DOI：