(2S,4R) methyl 1-[(E)-3-(3,4-diacetyloxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate | 769970-67-4

• 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) methyl 1-[(E)-3-(3,4-diacetyloxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate
• 英文别名: methyl (2S,4R)-1-[(E)-3-(3,4-diacetyloxyphenyl)prop-2-enoyl]-4-methylsulfonyloxypyrrolidine-2-carboxylate
• CAS: 769970-67-4
• 化学式: C₂₀H₂₃NO₁₀S
• 分子量: 469.469
• InChiKey: FTQZBHXHPLITSR-DODUIYEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,4R) methyl 1-[(E)-3-(3,4-diacetyloxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以54.8%的产率得到(2S,4R) methyl 1-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  Design, synthesis, and activity of caffeoyl pyrrolidine derivatives as potential gelatinase inhibitors

  摘要：

  The synthesis and biological evaluation of caffonyl pyrrolidine derivatives as MMPs inhibitors are reported in this paper. Inhibiting activities of synthesized compounds on gelatinase (MMP-2 and -9) were tested by using succinylated gelatin as substrate. Structure-activity relationship results from these tested compounds demonstrated that longer and more flexible side chain linked to the pyrrolidine ring at C-4 produced higher activity at gelatinase. Furthermore, aromatic heterocycle and sulfamide in the same position could enhance the activities. Compounds with free phenol hydroxyl group showed higher activity compared to methylated derivatives (or counterparts), which confirms the importance of phenol hydroxyl functionality in the interaction with gelatinase. The anti-metastasis model of mice bearing H-22 tumor cell was used to evaluate their in vivo inhibiting activities. All tested compounds were orally administered at a dose of 50 or 100 mg/kg, 6 days/week for two weeks. The test results demonstrated that most of these inhibitors showed significant anti-cancer activities (inhibitory rate > 35%) and were devoid of toxic effects. Compound 29 showed the highest inhibitory rate at 69.25%, indicating that it might be a promising lead compound. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.025
• 作为产物：
  描述：

  TRANS-咖啡酸 在 氯化亚砜 、 硫酸 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 、 苯 为溶剂， 反应 11.0h， 生成 (2S,4R) methyl 1-[(E)-3-(3,4-diacetyloxyphenyl)-2-propenoyl]-4-[(methylsulfonyl)oxy]-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  Design, synthesis, and activity of caffeoyl pyrrolidine derivatives as potential gelatinase inhibitors

  摘要：

  The synthesis and biological evaluation of caffonyl pyrrolidine derivatives as MMPs inhibitors are reported in this paper. Inhibiting activities of synthesized compounds on gelatinase (MMP-2 and -9) were tested by using succinylated gelatin as substrate. Structure-activity relationship results from these tested compounds demonstrated that longer and more flexible side chain linked to the pyrrolidine ring at C-4 produced higher activity at gelatinase. Furthermore, aromatic heterocycle and sulfamide in the same position could enhance the activities. Compounds with free phenol hydroxyl group showed higher activity compared to methylated derivatives (or counterparts), which confirms the importance of phenol hydroxyl functionality in the interaction with gelatinase. The anti-metastasis model of mice bearing H-22 tumor cell was used to evaluate their in vivo inhibiting activities. All tested compounds were orally administered at a dose of 50 or 100 mg/kg, 6 days/week for two weeks. The test results demonstrated that most of these inhibitors showed significant anti-cancer activities (inhibitory rate > 35%) and were devoid of toxic effects. Compound 29 showed the highest inhibitory rate at 69.25%, indicating that it might be a promising lead compound. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.025

文献信息

• Design, synthesis, and activity of caffeoyl pyrrolidine derivatives as potential gelatinase inhibitors
  作者：Ya-Lin Li、Wen-Fang Xu

  DOI：10.1016/j.bmc.2004.07.025

  日期：2004.10

  The synthesis and biological evaluation of caffonyl pyrrolidine derivatives as MMPs inhibitors are reported in this paper. Inhibiting activities of synthesized compounds on gelatinase (MMP-2 and -9) were tested by using succinylated gelatin as substrate. Structure-activity relationship results from these tested compounds demonstrated that longer and more flexible side chain linked to the pyrrolidine ring at C-4 produced higher activity at gelatinase. Furthermore, aromatic heterocycle and sulfamide in the same position could enhance the activities. Compounds with free phenol hydroxyl group showed higher activity compared to methylated derivatives (or counterparts), which confirms the importance of phenol hydroxyl functionality in the interaction with gelatinase. The anti-metastasis model of mice bearing H-22 tumor cell was used to evaluate their in vivo inhibiting activities. All tested compounds were orally administered at a dose of 50 or 100 mg/kg, 6 days/week for two weeks. The test results demonstrated that most of these inhibitors showed significant anti-cancer activities (inhibitory rate > 35%) and were devoid of toxic effects. Compound 29 showed the highest inhibitory rate at 69.25%, indicating that it might be a promising lead compound. (C) 2004 Elsevier Ltd. All rights reserved.