(2S,4R)-4-羟基-1-(萘-2-磺酰基)-吡咯烷-2-羧酸甲酯 | 391671-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (2S,4R)-4-羟基-1-(萘-2-磺酰基)-吡咯烷-2-羧酸甲酯
• 英文名称: (2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid methyl ester；methyl (2S,4R)-4-hydroxy-1-naphthalen-2-ylsulfonylpyrrolidine-2-carboxylate
• CAS: 391671-83-3
• 化学式: C₁₆H₁₇NO₅S
• 分子量: 335.381
• InChiKey: BLIDANQMSARENI-HIFRSBDPSA-N

物化性质

• 沸点：
  533.3±60.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (2S,4R)-4-羟基-1-(萘-2-磺酰基)-吡咯烷-2-羧酸甲酯 在 甲烷磺酸 、 三乙胺 、 三苯基膦 作用下， 以 水 、 甲苯 为溶剂， 以63.7 g (86%)的产率得到(2S,4S)-4-Methanesulfonyloxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Pyrrolidine derivatives

  摘要：

  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。

  公开号：

  US20020049243A1
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯盐酸盐 、 2-萘磺酰氯 在 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以82%的产率得到(2S,4R)-4-羟基-1-(萘-2-磺酰基)-吡咯烷-2-羧酸甲酯
  参考文献：
  名称：

  Endothelin-Converting Enzyme-1 Inhibition and Growth of Human Glioblastoma Cells

  摘要：

  Endothelin-1 (ET-1) is mitogenic and/or antiapoptotic in human cancers, and antagonists to ET-1 receptors are under evaluation for cancer treatment. Inhibition of ET-1 activation by the endothelin-converting enzymes 1(a-d) (ECE-1(a-d); EC 3.4.24.71) represents another approach to block the ET-1 effect in cancer. To evaluate this potential, we synthesized and characterized a series of low nanomolar nonpeptidic thiol-containing ECE-1 inhibitors, and evaluated their effect, as well as the effect of inhibitors for the related metalloproteases neprilysin (NEP; EC 3.4.24.11) and angiotensin-converting enzyme (ACE: EC 3.4.15.1). on human glioblastoma cell growth. Only ECE-1 inhibitors inhibited DNA synthesis by human glioblastoma cells. Exogenous addition of ET-1 or bigET-1 to glioblastoma cells did not counterbalance the growth inhibition elicited by ECE-1 inhibitors, suggesting that ECE-1 inhibitors block the proliferation of human glioblastoma cells most likely via a mechanism not involving extracellular production of ET-1. This class of molecules may thus represent novel therapeutic agents for the potential treatment of human cancer.

  DOI：

  10.1021/jm040857x

文献信息

• 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 compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US06444829B1

  公开（公告）日：2002-09-03

  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物可接受的酯和/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，并且对于治疗与血管收缩增加有关的疾病状态有效。
• PYRROLIDINE DERIVATIVES AS INHIBITORS OF ENDOTHELIN-CONVERTING ENZYME
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1303485A1

  公开（公告）日：2003-04-23
• 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