1-O-tert-butyl 3-O-methyl (3S,4S)-4-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]pyrrolidine-1,3-dicarboxylate | 362488-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-O-tert-butyl 3-O-methyl (3S,4S)-4-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]pyrrolidine-1,3-dicarboxylate
• CAS: 362488-44-6
• 化学式: C₂₉H₃₃N₃O₆
• 分子量: 519.598
• InChiKey: RMKZXMYJSMCBGH-UKILVPOCSA-N

物化性质

• 沸点：
  687.6±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 3-O-methyl (3S,4S)-4-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]pyrrolidine-1,3-dicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl (3S,4S)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-α converting enzyme (TACE)

  摘要：

  Selective inhibitors of TNF-alpha Converting Enzyme (TACE) based on (1R,2S)-cyclopentyl, (3S,4S)-pyrrolidinyl, and (3R,4S)-tetrahydrofuranyl beta-benzamido hydroxamic acids have been synthesized and evaluated. This study has led to the discovery of novel inhibitors whose profiles include activity against TACE in an enzyme assay, potency in the suppression of LPS-stimulated TNF-alpha in human whole blood, selectivity against a panel of MMPs and oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.059
• 作为产物：
  描述：

  4-[(2-甲基-4-喹啉基)甲氧基]-苯甲酸 、 (3S,4S)-1-tert-Butyl 3-methyl 4-aminopyrrolidine-1,3-dicarboxylate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-O-tert-butyl 3-O-methyl (3S,4S)-4-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]pyrrolidine-1,3-dicarboxylate 、 1-(tert-butyl) 3-methyl (3R,4R)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-1,3-dicarboxylate
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-α converting enzyme (TACE)

  摘要：

  Selective inhibitors of TNF-alpha Converting Enzyme (TACE) based on (1R,2S)-cyclopentyl, (3S,4S)-pyrrolidinyl, and (3R,4S)-tetrahydrofuranyl beta-benzamido hydroxamic acids have been synthesized and evaluated. This study has led to the discovery of novel inhibitors whose profiles include activity against TACE in an enzyme assay, potency in the suppression of LPS-stimulated TNF-alpha in human whole blood, selectivity against a panel of MMPs and oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.059

文献信息

• Triazolone and triazolethione derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme
  申请人：——

  公开号：US20040116491A1

  公开（公告）日：2004-06-17

  The present application describes novel hydantoin derivatives of formula (I): 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, L, and R 11 are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-&agr; converting enzyme (TACE), aggrecanase, or a combination thereof.

  本申请描述了式 (I) 的新型海因衍生物： 1 或其药学上可接受的盐或原药形式，其中 A、L 和 R 11 可用作基质金属蛋白酶 (MMP)、TNF-&agr; 转换酶 (TACE)、凝集素酶或其组合的抑制剂。
• EP1558581A4
  申请人：——

  公开号：EP1558581A4

  公开（公告）日：2007-07-25
• TRIAZOLONE AND TRIAZOLETHIONE DERIVATIVES
  申请人：Bristol-Myers Squibb Company

  公开号：EP1558581A2

  公开（公告）日：2005-08-03
• US7074810B2
  申请人：——

  公开号：US7074810B2

  公开（公告）日：2006-07-11
• [EN] TRIAZOLONE AND TRIAZOLETHIONE DERIVATIVES AS INHIBITORS OF MATRIX METALLOPROTEINASES AND/OR TNF-ALPHA CONVERTING ENZYME<br/>[FR] DERIVES DE LA TRIAZOLONE ET DE LA TRIAZOLETHIONE, INHIBITEURS DES METALLOPROTEINASES DE MATRICES ET/OU DE L'ENZYME DE CONVERSION DU TNF DOLLAR G(A)
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004032846A2

  公开（公告）日：2004-04-22

  The present application describes novel hydantoin derivatives of formula (I): or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, L, and R11 are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-a converting enzyme (TACE), aggrecanase, or a combination thereof.