((3SR,4SR)-1-tert-butoxycarbonyl)4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid | 252919-44-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ((3SR,4SR)-1-tert-butoxycarbonyl)4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid
• 英文别名: (3S,4S)-1-(Tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid；(3S,4S)-4-ethoxycarbonyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid
• CAS: 252919-44-1
• 化学式: C₁₃H₂₁NO₆
• mdl: MFCD29038963
• 分子量: 287.313
• InChiKey: BHOJIKSQYLVZHD-RKDXNWHRSA-N

物化性质

• 沸点：
  405.4±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3SR,4SR)-1-tert-butoxycarbonyl)4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 (3S,4S)-1-benzenesulfonyl-4-(morpholine-4-carbonyl)pyrrolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Identification of Potent and Selective Cathepsin S Inhibitors Containing Different Central Cyclic Scaffolds

  摘要：

  Starting from the weakly active dual CatS/K inhibitor 5, structure-based design supported by X-ray analysis led to the discovery of the potent and selective (>50 000-fold vs CatK) cyclopentane derivative 22 by exploiting specific ligand-receptor interactions in the S2 pocket of CatS. Changing the central cyclopentane scaffold to the analogous pyrrolidine derivative 57 decreased the enzyme as well as the cell-based activity significantly by 24- and 69-fold, respectively. The most promising scaffold identified was the readily accessible proline derivative (e.g., 79). This compound, with an appealing ligand efficiency (LE) of 0.47, included additional structural modifications binding in the Si and S3 pockets of CatS, leading to favorable in vitro and in vivo properties. Compound 79 reduced IL-2 production in a transgenic DO10.11 mouse model of antigen presentation in a dose-dependent manner with an ED50 of 5 mg/kg.

  DOI：

  10.1021/jm401528k
• 作为产物：
  描述：

  富马酸二乙酯 在 palladium on activated charcoal sodium hydroxide 、 Lipase OF 、 氢气 、 sodium chloride 作用下， 以 phosphate buffer 、 乙醇 、 甲苯 为溶剂， 反应 5.5h， 生成 ((3SR,4SR)-1-tert-butoxycarbonyl)4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  Chemoenzymatic preparation of non-racemic N-Boc-pyrrolidine-3,4-dicarboxylic acid 3-ethyl esters and their 4-hydroxymethyl derivatives

  摘要：

  For the synthesis of metalloproteinase inhibitors the (R,R)- and (S,S)-monoethyl esters of N-Boe-pyrrolidine-3,4-dicarboxylic acid were prepared as key intermediates from the trans-diester racemate by two consecutive, highly selective enzymatic reactions. Reduction of the formed acids to the corresponding enantiopure hydroxymethyl derivatives ((R,R)- and (S,S)-ethyl N-Boc-4-hydroxymethyl-3-carboxylate) gives access to a new series of chiral building blocks. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00284-2

文献信息

• PENTACYCLIC HETEROCYCLES
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20200283452A1

  公开（公告）日：2020-09-10

  The present invention provides compounds represented by formulas (I) to (XVII) or pharmaceutically acceptable salts thereof:

  本发明提供了由式(I)至(XVII)表示的化合物或其药学上可接受的盐：
• [EN] TLR2 MODULATOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSÉS MODULATEURS DE TLR2, COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：AXIAL THERAPEUTICS INC

  公开号：WO2021242923A1

  公开（公告）日：2021-12-02

  The present disclosure relates to compounds which modulate the activity of Toll-like receptor (TLR) proteins, including agonists or activators, partial agonists, and antagonists. Of particular interest of compounds that modulate the activity of TLR2, as well as methods of using such compounds to treat cancer and other disorders associated with a TLR2 pathway.

  本公开涉及调节Toll样受体（TLR）蛋白活性的化合物，包括激动剂或激活剂、部分激动剂和拮抗剂。特别感兴趣的是调节TLR2活性的化合物，以及使用这些化合物治疗与TLR2通路相关的癌症和其他疾病的方法。
• Organic Compounds
  申请人：Ehrhardt Claus

  公开号：US20080194549A1

  公开（公告）日：2008-08-14

  The invention relates to the use of (3,4-di-, 3,3,4-tri, 3,4,4-tri- or 3,3,4,4-tetra-)substituted pyrrolidine compounds for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; compounds that are part of a subclass of these substituted pyrrolidine compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; new compounds that are part of a subclass of these substituted pyrrolidine compounds; pharmaceutical formulations comprising said substituted pyrrolidine compounds, and/or a method of treatment comprising administering said substituted pyrrolidine compounds, a method for the manufacture especially of said new substituted pyrrolidine compounds, as well as novel intermediates, starting materials and/or partial steps for their synthesis.

  本发明涉及使用(3,4-二-, 3,3,4-三-, 3,4,4-三-或3,3,4,4-四-)取代吡咯烷化合物制备治疗依赖于肾素活性的疾病的药物制剂；使用该类化合物治疗依赖于肾素活性的疾病；该取代吡咯烷化合物亚类的化合物用于温血动物的诊断和治疗，特别是用于治疗依赖于肾素活性的疾病；该取代吡咯烷化合物亚类的新化合物；包括所述取代吡咯烷化合物的药物制剂和/或包括给予所述取代吡咯烷化合物的治疗方法，特别是制备该新取代吡咯烷化合物的方法，以及其合成的新中间体、起始材料和/或部分步骤。
• HIV PROTEASE INHIBITORS
  申请人：Coburn Craig A.

  公开号：US20120142752A1

  公开（公告）日：2012-06-07

  Compounds of Formula (I) are disclosed; wherein X A , k, A, B, R 3A , R 3B , R 4 and R 5 are defined herein. The compounds of Formula (I) are HIV protease inhibitors. The compounds and their pharmaceutically acceptable salts are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公开了化学式（I）的化合物；其中XA，k，A，B，R3A，R3B，R4和R5在此定义。化合物（I）是HIV蛋白酶抑制剂。化合物及其药学上可接受的盐可用于预防或治疗HIV感染以及预防，治疗或延迟艾滋病的发作。这些化合物及其盐可作为制药组合物的成分，可选地与其他抗病毒药物，免疫调节剂，抗生素或疫苗组合使用。
• Organic compounds
  申请人：Novartis AG

  公开号：US07807709B2

  公开（公告）日：2010-10-05

  The invention relates to the use of (3,4-di-, 3,3,4-tri, 3,4,4-tri- or 3,3,4,4-tetra-)substituted pyrrolidine compounds for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; compounds that are part of a subclass of these substituted pyrrolidine compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; new compounds that are part of a subclass of these substituted pyrrolidine compounds; pharmaceutical formulations comprising said substituted pyrrolidine compounds, and/or a method of treatment comprising administering said substituted pyrrolidine compounds, a method for the manufacture especially of said new substituted pyrrolidine compounds, as well as novel intermediates, starting materials and/or partial steps for their synthesis.

  本发明涉及使用（3,4-二-, 3,3,4-三-, 3,4,4-三-或3,3,4,4-四-）取代吡咯烷化合物来制备用于治疗依赖于肾素活性的疾病的药物制剂；该类化合物在治疗依赖于肾素活性的疾病中的使用；属于这些取代吡咯烷化合物亚类的化合物用于诊断和治疗温血动物，特别是用于治疗依赖于肾素活性的疾病（=失调）；属于这些取代吡咯烷化合物亚类的新化合物；包含所述取代吡咯烷化合物的药物制剂，和/或包括给予所述取代吡咯烷化合物的治疗方法，一种用于特别制备这些新的取代吡咯烷化合物的方法，以及其合成的新中间体，起始材料和/或部分步骤。