(S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid | 227616-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid
• 英文别名: (6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid；(6S)-4-oxo-3-(phenylmethoxycarbonylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid
• CAS: 227616-77-5
• 化学式: C₁₆H₁₅N₃O₅
• 分子量: 329.312
• InChiKey: CFCZQAXWWZLCNS-LBPRGKRZSA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 生成 (S)-allyl-(8,8-diethyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic Acid Benzyl Ester
  参考文献：
  名称：

  Design and synthesis of bicyclic pyrazinone and pyrimidinone amides as potent TF–FVIIa inhibitors

  摘要：

  Bicyclic pyrazinone and pyrimidinone amides were designed and synthesized as potent TF-FVIIa inhibitors. SAR demonstrated that the S2 and S3 pockets of FVIIa prefer to bind small, lipophilic groups. An Xray crystal structure of optimized compound 9b bound in the active site of FVIIa showed that the bicyclic scaffold provides 5 hydrogen bonding interactions in addition to projecting groups for interactions within the S1, S2 and S3 pockets. Compound 9b showed excellent FVIIa potency, good selectivity against FIXa, Xa, XIa and chymotrypsin, and good clotting activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.094
• 作为产物：
  描述：

  tert-Butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylate 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  Bicyclic pyrimidinones as coagulation cascade inhibitors

  摘要：

  本发明一般涉及抑制丝氨酸蛋白酶的化合物。具体而言，本发明涉及式（I）的新型氨基双环嘧啶酮化合物或其立体异构体或药学上可接受的盐形式，这些化合物可用作凝血级联中丝氨酸蛋白酶的选择性抑制剂；例如凝血酶、X因子a、XI因子a、IX因子a和/或VII因子a。特别是，涉及抑制VII因子a的化合物。本发明还涉及包含这些化合物的药物组合物以及使用相同的方法。

  公开号：

  US20040006065A1

文献信息

• Inhibitors of hepatitis C virus NS3 protease
  申请人：——

  公开号：US20030064962A1

  公开（公告）日：2003-04-03

  The present invention relates generally to a novel class of pyrimidinones of Formula (I): 1 that are useful as serine protease inhibitors, and more particularly as Hepatitis C virus NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

  本发明一般涉及一种新型的嘧啶酮类化合物，具有如下式（I）所示的结构，这些化合物可用作丝氨酸蛋白酶抑制剂，更具体地作为丙型肝炎病毒NS3蛋白酶抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些药物的方法。
• Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors
  作者：Peter W Glunz、Brent D Douty、Carl P Decicco

  DOI：10.1016/s0960-894x(03)00022-2

  日期：2003.3

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.
• US6653295B2
  申请人：——

  公开号：US6653295B2

  公开（公告）日：2003-11-25
• US7094783B2
  申请人：——

  公开号：US7094783B2

  公开（公告）日：2006-08-22
• [EN] INHIBITORS OF HEPATITIS C VIRUS NS3 PROTEASE<br/>[FR] INHIBITEURS DE LA PROTEASE NS3 DU VIRUS DE L'HEPATITE C
  申请人：BRISTOL MYERS SQUIBB PHARMA CO

  公开号：WO2002048116A2

  公开（公告）日：2002-06-20

  The present invention relates generally to a novel class of pyrimidinones of Formula (I) that are useful as serine protease inhibitors, and more particularly as Hepatitis C virus NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.