(2S,4R)-4-Hydroxy-1-[(E)-3-(4-methoxy-phenyl)-acryloyl]-pyrrolidine-2-carboxylic acid methyl ester | 915231-91-3

• 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: (2S,4R)-4-Hydroxy-1-[(E)-3-(4-methoxy-phenyl)-acryloyl]-pyrrolidine-2-carboxylic acid methyl ester
• CAS: 915231-91-3
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: CSWGTQGFSWPKLM-MZMNXDGSSA-N

物化性质

• 沸点：
  530.6±50.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-Hydroxy-1-[(E)-3-(4-methoxy-phenyl)-acryloyl]-pyrrolidine-2-carboxylic acid methyl ester 、 4-氯苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以69.5%的产率得到(2S,4R)-4-(4-Chloro-benzoyloxy)-1-[(E)-3-(4-methoxy-phenyl)-acryloyl]-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of new cinnamoyl pyrrolidine derivatives as potent gelatinase inhibitors

  摘要：

  A series of new cinnamoyl pyrrolidine derivatives have been synthesized based on the L-hydroxyproline scaffold and inhibiting activities on gelatinase (MMP-2 and -9) and APN were tested. Structure-activity relationship studies showed that the side chain with aromatic ring at C4 in pyrrolidine ring showed better inhibitory activities on gelatinase than aliphatic side chain. Most compounds exhibited poor activities on APN compared with MMP-2. Within this series, three compounds, A8, B9 and C10, have the good potency (IC50 = 5.2-9.7 nM) and could be used as lead compounds in the future. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.015
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 (2S,4R)-4-Hydroxy-1-[(E)-3-(4-methoxy-phenyl)-acryloyl]-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and preliminary evaluation of new cinnamoyl pyrrolidine derivatives as potent gelatinase inhibitors

  摘要：

  A series of new cinnamoyl pyrrolidine derivatives have been synthesized based on the L-hydroxyproline scaffold and inhibiting activities on gelatinase (MMP-2 and -9) and APN were tested. Structure-activity relationship studies showed that the side chain with aromatic ring at C4 in pyrrolidine ring showed better inhibitory activities on gelatinase than aliphatic side chain. Most compounds exhibited poor activities on APN compared with MMP-2. Within this series, three compounds, A8, B9 and C10, have the good potency (IC50 = 5.2-9.7 nM) and could be used as lead compounds in the future. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.015