(S)-2-(pyridin-4-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester | 872254-14-3

• 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: (S)-2-(pyridin-4-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (S)-2-((pyridin-4-yloxy)methyl)pyrrolidine-1-carboxylate；2-(pyridin-4-yl-oxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester；tert-Butyl (2S)-2-[(pyridin-4-yloxy)methyl]pyrrolidine-1-carboxylate；tert-butyl (2S)-2-[(pyridine-4-yloxy)methyl]pyrrolidine-1-carboxylate；tert-butyl (2S)-2-(pyridin-4-yloxymethyl)pyrrolidine-1-carboxylate
• CAS: 872254-14-3
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: FUHBRKWTDBRYLS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(pyridin-4-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 5-(2-(pyridin-4-yl-oxymethyl)-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  N-Benzylisatin Sulfonamide Analogues as Potent Caspase-3 Inhibitors:  Synthesis, in Vitro Activity, and Molecular Modeling Studies

  摘要：

  A number of isatin sulfonamide analogues were prepared and their potencies for inhibiting caspase-1, -3, -6, -7, and -8 were evaluated in vitro. Several compounds displaying a nanomolar potency for inhibiting the executioner caspases, caspase-3 and caspase-7, were identified. These compounds were also observed to have a low potency for inhibiting the initiator caspases, caspase-1 and caspase-8, and caspase-6. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The results of the current study revealed a number of non-peptide-based caspase inhibitors that may be useful in assessing the role of inhibiting the executioner caspases in minimizing tissue damage in disease conditions characterized by unregulated apoptosis.

  DOI：

  10.1021/jm0506625
• 作为产物：
  描述：

  N-Boc-L-脯氨醇 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.67h， 生成 (S)-2-(pyridin-4-yloxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N-Benzylisatin Sulfonamide Analogues as Potent Caspase-3 Inhibitors:  Synthesis, in Vitro Activity, and Molecular Modeling Studies

  摘要：

  A number of isatin sulfonamide analogues were prepared and their potencies for inhibiting caspase-1, -3, -6, -7, and -8 were evaluated in vitro. Several compounds displaying a nanomolar potency for inhibiting the executioner caspases, caspase-3 and caspase-7, were identified. These compounds were also observed to have a low potency for inhibiting the initiator caspases, caspase-1 and caspase-8, and caspase-6. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The results of the current study revealed a number of non-peptide-based caspase inhibitors that may be useful in assessing the role of inhibiting the executioner caspases in minimizing tissue damage in disease conditions characterized by unregulated apoptosis.

  DOI：

  10.1021/jm0506625

文献信息

• Simple Chiral Pyrrolidine–Pyridine-Based Catalysts for Highly Enantioselective Michael Addition to Nitro Olefins
  作者：Da-Zhen Xu、Sen Shi、Yongmei Wang

  DOI：10.1002/ejoc.200900716

  日期：2009.10

  of chiral pyrrolidine–pyridine-based organocatalysts, available from commercially available starting materials, have been synthesized and shown to be very effective catalysts for the asymmetric Michael addition reactions of cyclic/acyclic/aromatic ketones and an aldehyde with nitro olefins, giving excellent yields (up to 99 %), diastereoselectivities (syn/anti = 99:1), and enantioselectivities (up

  已经合成了一类新的手性吡咯烷-吡啶基有机催化剂，可从市售原料中获得，并被证明是非常有效的催化剂，用于环状/无环/芳香酮和醛与硝基烯烃的不对称迈克尔加成反应，得到出色的产率（高达 99%）、非对映选择性（syn/anti = 99:1）和对映选择性（高达 99%）。基于中间体的实验结果和ESI-MS分析，推导出了有机催化剂与底物的活性模式。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Imidazothiazole derivatives
  申请人：Kawato Haruko

  公开号：US20090312310A1

  公开（公告）日：2009-12-17

  There is provided a novel compound that inhibits interaction between murine double minute 2 (Mdm2) protein and p53 protein and exhibits anti-tumor activity. The present invention provides an imidazothiazole derivative represented by the following formula (1) having various substituents that inhibits interaction between Mdm2 protein and p53 protein and exhibits anti-tumor activity: wherein R 1 , R 2 , R 3 , R 4 , and R 5 in the formula (1) each has the same meaning as defined in the specification.

  提供了一种新的化合物，它抑制小鼠双分子分钟2（Mdm2）蛋白与p53蛋白之间的相互作用，并展现出抗肿瘤活性。本发明提供了一种咪唑噻唑衍生物，其表示为以下公式（1），具有各种取代基，可抑制Mdm2蛋白与p53蛋白之间的相互作用并展现出抗肿瘤活性：其中，公式（1）中的R1、R2、R3、R4和R5每个都具有规范中定义的相同含义。
• Pyrrolidine–pyridine base catalysts for the enantioselective Michael addition of ketones to chalcones
  作者：Da-Zhen Xu、Sen Shi、Yingjun Liu、Yongmei Wang

  DOI：10.1016/j.tet.2009.09.001

  日期：2009.11

  A series of pyrrolidine-pyridine base organocatalysts have been developed and 3a found to be a highly effective catalyst for the asymmetric Michael addition reactions of ketones to chalcones. The reaction generated the corresponding products 1, 5-diketones in excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 100% ee). (c) 2009 Elsevier Ltd. All rights reserved.
• <i>N</i>-Benzylisatin Sulfonamide Analogues as Potent Caspase-3 Inhibitors:  Synthesis, in Vitro Activity, and Molecular Modeling Studies
  作者：Wenhua Chu、Jun Zhang、Chenbo Zeng、Justin Rothfuss、Zhude Tu、Yunxiang Chu、David E. Reichert、Michael J. Welch、Robert H. Mach

  DOI：10.1021/jm0506625

  日期：2005.12.1

  A number of isatin sulfonamide analogues were prepared and their potencies for inhibiting caspase-1, -3, -6, -7, and -8 were evaluated in vitro. Several compounds displaying a nanomolar potency for inhibiting the executioner caspases, caspase-3 and caspase-7, were identified. These compounds were also observed to have a low potency for inhibiting the initiator caspases, caspase-1 and caspase-8, and caspase-6. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The results of the current study revealed a number of non-peptide-based caspase inhibitors that may be useful in assessing the role of inhibiting the executioner caspases in minimizing tissue damage in disease conditions characterized by unregulated apoptosis.