trans-4-Hydroxy-1-methanesulfonyl-pyrrolidine-2-carboxylic acid methyl ester | 391671-88-8

• 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: trans-4-Hydroxy-1-methanesulfonyl-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4R)-4-hydroxy-1-methylsulfonylpyrrolidine-2-carboxylate
• CAS: 391671-88-8
• 化学式: C₇H₁₃NO₅S
• 分子量: 223.25
• InChiKey: CHMKPIIZEKXJIC-RITPCOANSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  361.9±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  trans-4-Hydroxy-1-methanesulfonyl-pyrrolidine-2-carboxylic acid methyl ester 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以46%的产率得到4-Hydroxy-1-methanesulfonyl-pyrrolidine-2-carboxylicacid hydroxyamide
  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
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯盐酸盐 、 甲基磺酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以35%的产率得到trans-4-Hydroxy-1-methanesulfonyl-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

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020049243A1

  公开（公告）日：2002-04-25

  The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

  本发明涉及吡咯烷衍生物及其二聚体形式和/或药用可接受的酯和/或盐。这些化合物可用作金属蛋白酶抑制剂，例如锌蛋白酶，特别是锌水解酶，对治疗与血管收缩增加发生相关的疾病状态有效。
• PYRROLIDINE COMPOUNDS
  申请人：——

  公开号：US20020040048A1

  公开（公告）日：2002-04-04

  The present invention relates to a pyrrolidine compound and pharmaceutically acceptable esters and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

  本发明涉及吡咯烷化合物及其药用可接受的酯和/或盐。这些化合物可用作金属蛋白酶抑制剂，例如锌蛋白酶，特别是锌水解酶，对治疗与血管收缩增加发生相关的疾病状态有效。
• PYRROLIDINE-2-CARBOXYLIC ACID HYDRAZIDE DERIVATIVES FOR USE AS METALLOPROTEASE INHIBITORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1317428B1

  公开（公告）日：2006-04-19
• US6444829B1
  申请人：——

  公开号：US6444829B1

  公开（公告）日：2002-09-03
• US6541638B2
  申请人：——

  公开号：US6541638B2

  公开（公告）日：2003-04-01