1-Benzenesulfonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester | 1076189-64-4

• 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: 1-Benzenesulfonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4R)-1-(benzenesulfonyl)-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate
• CAS: 1076189-64-4
• 化学式: C₁₉H₂₁NO₇S₂
• 分子量: 439.51
• InChiKey: BPAHUPZKRPSBLZ-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (2S,4R)-4-hydroxy-1-benzenesulfonylpyrrolidine-2-carboxylate 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到1-Benzenesulfonyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A series of new sulfonyl pyrrolidine derivatives was designed, synthesized, and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The compounds 4c, 4j, 5a, and 5b were equally or more potent MMP-2 inhibitors than the positive control LY52. The FlexX docking was done to explain the reason for the different potency between MMP-2 and AP-N. Structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.073

文献信息

• Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors
  作者：Xian-Chao Cheng、Qiang Wang、Hao Fang、Wei Tang、Wen-Fang Xu

  DOI：10.1016/j.bmc.2008.07.073

  日期：2008.9

  A series of new sulfonyl pyrrolidine derivatives was designed, synthesized, and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The compounds 4c, 4j, 5a, and 5b were equally or more potent MMP-2 inhibitors than the positive control LY52. The FlexX docking was done to explain the reason for the different potency between MMP-2 and AP-N. Structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.