(1S,3aR,6aS)-2-[(benzyloxy)carbonyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid | 956332-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3aR,6aS)-2-[(benzyloxy)carbonyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid
• 英文别名: (1S,3AR,6aS)-2-((benzyloxy)carbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid；(3S,3aS,6aR)-2-phenylmethoxycarbonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxylic acid
• CAS: 956332-61-9
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: BBNDCGGBMRLLSD-IHRRRGAJSA-N

物化性质

• 沸点：
  472.8±38.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3aR,6aS)-2-[(benzyloxy)carbonyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid 在 戴斯-马丁氧化剂 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 benzyl (1S,3aR,6aS)-1-(((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)carbamoyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
  参考文献：
  名称：

  肠道病毒 D68 2A 蛋白酶抑制剂的基于结构的先导化合物优化

  摘要：

  肠道病毒 D68 （EV-D68） 病毒是一种非脊髓灰质炎肠道病毒，通常会导致呼吸道疾病，严重时可导致儿童瘫痪和死亡。目前尚无针对 EV-D68 的疫苗或抗病毒药物。我们之前发现病毒 2A 蛋白酶 （2Apro） 是一种可行的抗病毒药物靶点，并确定 telaprevir 是一种 2Apro 抑制剂。2Apro 是一种病毒半胱氨酸蛋白酶，可裂解病毒 VP1-2A 多蛋白连接。在这项研究中，我们报道了野生型 EV-D68 2Apro 和 C107A 突变体的 X 射线晶体结构以及特拉匹韦基于结构的先导化合物优化。在 X 射线晶体结构的引导下，我们使用分子动力学模拟预测了 telaprevir 在 2Apro 中的结合姿势。然后，我们利用该模型为特拉匹韦的反应性弹头和 P1-P4 替换的基于结构的优化提供信息。这些努力导致发现了 2Apro 抑制剂，其抗病毒活性优于 telaprevir。这些化合物代表了作为

  DOI：

  10.1021/acs.jmedchem.3c00995
• 作为产物：
  描述：

  (1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,3aR,6aS)-2-[(benzyloxy)carbonyl]octahydrocyclopenta[c]pyrrole-1-carboxylic acid
  参考文献：
  名称：

  US2022/332683

  摘要：

  公开号：

文献信息

• [EN] PROCESS FOR THE PREPARATION OF TELAPREVIR AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE TÉLAPRÉVIR ET D'INTERMÉDIAIRES DE TÉLAPRÉVIR
  申请人：RANBAXY LAB LTD

  公开号：WO2014203208A1

  公开（公告）日：2014-12-24

  The present invention provides a process for the preparation of telaprevir and intermediates thereof.

  本发明提供了一种用于制备特拉普韦和其中间体的过程。
• Synthesis, Characterization and Docking Studies of Anti-HCV Molecules
  作者：Satish Kumar、P.K. Santra、J. Dwivedi、R.C. Aryan

  DOI：10.14233/ajchem.2020.22618

  日期：——

  The present study reports the synthesis and characterization of novel molecules inhibiting the spread of hepatitis C. The molecules were designed as to block the NS3/4A protease enzyme on HCV RNA. The molecules were synthesized using usual peptide synthesis techniques. Compounds with purity more than 95% were characterized and docking studies were also performed. All the compounds were characterized using physico-chemical techniques such as determination of melting point by DSC and NMR, mass, IR spectral studies. The docking studies were also conducted to assess the activity of molecules for inhibition of hepatitis C virus.

  本研究报告了合成和表征抑制丙型肝炎传播的新型分子。这些分子被设计为阻断HCV RNA上的NS3/4A蛋白酶酶。这些分子是使用常规肽合成技术合成的。纯度超过95％的化合物进行了表征，并进行了对接研究。所有化合物均使用物理化学技术进行了表征，如通过DSC和NMR确定熔点，质量，红外光谱研究。对接研究也进行了以评估分子对抑制丙型肝炎病毒的活性。
• HCV NS5A replication complex inhibitors. Part 2: Investigation of stilbene prolinamides
  作者：Denis R. St. Laurent、Makonen Belema、Min Gao、Jason Goodrich、Ramesh Kakarla、Jay O. Knipe、Julie A. Lemm、Mengping Liu、Omar D. Lopez、Van N. Nguyen、Peter T. Nower、Donald O’Boyle、Yuping Qiu、Jeffrey L. Romine、Michael H. Serrano-Wu、Jin-Hua Sun、Lourdes Valera、Fukang Yang、Xuejie Yang、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1016/j.bmcl.2012.08.049

  日期：2012.10

  In a previous disclosure,(1) we reported the dimerization of an iminothiazolidinone to form 1, a contributor to the observed inhibition of HCV genotype 1b replicon activity. The dimer was isolated via bioassay-guided fractionation experiments and shown to be a potent inhibitor of genotype 1b HCV replication for which resistance mapped to the NS5A protein. The elements responsible for governing HCV inhibitory activity were successfully captured in the structurally simplified stilbene prolinamide 2. We describe herein the early SAR and profiling associated with stilbene prolinamides that culminated in the identification of analogs with PK properties sufficient to warrant continued commitment to this chemotype. These studies represent the key initial steps toward the discovery of daclatasvir (BMS-790052), a compound that has demonstrated clinical proof-of-concept for inhibiting the NS5A replication complex in the treatment of HCV infection. (C) 2012 Elsevier Ltd. All rights reserved.
• NOVEL SPIROPYRROLIDINE DERIVED ANTIVIRAL AGENTS
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US20220162231A1

  公开（公告）日：2022-05-26

  The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, thereof: which inhibit coronavirus replication activity. The invention further relates to pharmaceutical compositions comprising a compound of Formula (I) or a pharmaceutically acceptable salt thereof, and methods of treating or preventing a coronavirus infection in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt thereof.