methyl (2S,4R)-4-hydroxy-1-benzenesulfonylpyrrolidine-2-carboxylate | 20309-97-1

• 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,4R)-4-hydroxy-1-benzenesulfonylpyrrolidine-2-carboxylate
• 英文别名: N-phenylsulfonyl-trans-4-hydroxy-L-proline methyl ester；N-Benzolsulfonyl-trans-4-hydroxy-L-prolinmethylester；trans-4-Hydroxy-N-benzolsulfonyl-prolinmethylester；trans-1-Benzenesulfonyl-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester；methyl (2S,4R)-1-(benzenesulfonyl)-4-hydroxypyrrolidine-2-carboxylate
• CAS: 20309-97-1
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: KATQZGNGQJYXSJ-KOLCDFICSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  447.0±55.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,4R)-4-hydroxy-1-benzenesulfonylpyrrolidine-2-carboxylate 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以91%的产率得到methyl (S)-4-oxo-1-(phenylsulfonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A series of novel sulfonyl pyrrolidine derivatives were 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. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.027
• 作为产物：
  描述：

  (1S,4S)-5-(phenylsulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 在 四丁基溴化铵 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 128.0h， 生成 methyl (2S,4R)-4-hydroxy-1-benzenesulfonylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Studies on the Synthesis of cis-4-Hydroxy-L-proline

  摘要：

  我们开发出了一种高产的三步实用程序，该程序依赖于萃取加工程序，通过三个步骤将 N-苯磺酰基-反式-4-羟基-l-脯氨酸转化为 N-苯磺酰基-顺式-4-羟基-l-脯氨酸甲酯，收率高达 82%。

  DOI：

  10.1071/ch11204

文献信息

• Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors
  作者：Jian Zhang、Xiaoyang Li、Yuqi Jiang、Jinhong Feng、Xiaoguang Li、Yingjie Zhang、Wenfang Xu

  DOI：10.1016/j.bmc.2013.12.025

  日期：2014.6

  A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds

  设计，合成和测定了一系列新型的α-磺酰基γ-（甘氨酰氨基）脯氨酸拟肽衍生物，它们对基质金属蛋白酶-2（MMP-2），氨基肽酶N（APN）/ CD13和HDAC的活性。结果表明，与APN和HDAC相比，所有化合物均显示出对MMP-2的高度选择性抑制。还研究了某些化合物对SKOV3，HL60和A549细胞的抗增殖活性。与对照LY52相比，在酶促抑制分析和基于细胞的分析中均具有优异活性的化合物12u可用作进一步开发MMP抑制剂的先导化合物。
• Cell adhesion inhibitors
  申请人：Lee Wen-Cherng

  公开号：US20060014966A1

  公开（公告）日：2006-01-19

  Cell adhesion inhibitors can interact with VLA-4 molecules and inhibits VLA-4 dependent cell adhesion. An inhibitor including a polyethylene glycol moiety can have advantageous pharmaceutical properties.

  细胞黏附抑制剂可以与VLA-4分子相互作用并抑制VLA-4依赖的细胞黏附。包括聚乙二醇基团的抑制剂可以具有优越的药物特性。
• 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.
• US7196112B2
  申请人：——

  公开号：US7196112B2

  公开（公告）日：2007-03-27
• Studies on the Synthesis of cis-4-Hydroxy-L-proline
  作者：Jessica A. Smith、G. Paul Savage、Oliver E. Hutt

  DOI：10.1071/ch11204

  日期：——

  A high yielding practical three-step procedure, which relies on an extractive work-up procedure, has been developed to convert N-phenylsulfonyl-trans-4-hydroxy-l-proline to N-phenylsulfonyl-cis-4-hydroxy-l-proline methyl ester in 82 % yield over three steps.

  我们开发出了一种高产的三步实用程序，该程序依赖于萃取加工程序，通过三个步骤将 N-苯磺酰基-反式-4-羟基-l-脯氨酸转化为 N-苯磺酰基-顺式-4-羟基-l-脯氨酸甲酯，收率高达 82%。