(S)-2-styryl-N-Boc-pyrrolidine | 220510-68-9

• 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-styryl-N-Boc-pyrrolidine
• 英文别名: 1-tBoc-2-styrenyl pyrrolidine；(s)-(+)-n-Boc-2-styrylpyrrolidine；tert-butyl (2S)-2-(2-phenylethenyl)pyrrolidine-1-carboxylate
• CAS: 220510-68-9
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: JFLBTLCVLDWTIG-HNNXBMFYSA-N

物化性质

• 沸点：
  376.1±31.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-styryl-N-Boc-pyrrolidine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity

  摘要：

  Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4R alpha bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.

  DOI：

  10.1021/acs.jmedchem.5b01321
• 作为产物：
  描述：

  N-Boc-L-脯氨醇 在 N-甲基咪唑 、 2,2'-联吡啶 、 正丁基锂 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 1.08h， 生成 (S)-2-styryl-N-Boc-pyrrolidine
  参考文献：
  名称：

  手性磷-烯烃配体，用于RhI催化芳基硼酸不对称加成至电子不足的烯烃

  摘要：

  衍生自刚性“特权” 1-脯氨酸的新型手性磷-烯烃杂化配体已在室温下方便地制备并应用于铑催化的缺电子烯烃与芳基硼酸的不对称芳基化反应。该反应以优异的产率和高对映选择性提供了所需的产物。观察到的立体选择性的起源已通过密度泛函理论（DFT）计算进行了研究。

  DOI：

  10.1002/asia.201600143

文献信息

• Sulfonyl isatin compounds and methods of blocking apoptosis therewith
  申请人：SmithKline Beecham Corporation

  公开号：US06403792B1

  公开（公告）日：2002-06-11

  The present invention is to novel sulfonyl isatin compounds of Formula (I), their pharmaceutical compositions, and the novel inhibition of caspases for use in the treatment of apoptosis, and disease states caused by excessive or inappropriate cell death.

  本发明涉及一种新型的磺酰基异喹啉化合物（式（I）），它们的药物组合物，以及用于治疗细胞凋亡和由过度或不适当的细胞死亡引起的疾病状态的新型半胱氨酸蛋白酶抑制剂。
• [EN] MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS<br/>[FR] MODULATEURS DE NEUROTRANSMETTEURS DU SYSTEME NERVEUX CENTRAL
  申请人：HUMAN BIOMOLECULAR RES INST

  公开号：WO2006025920A3

  公开（公告）日：2006-08-17
• Chiral Phosphorus-Olefin Ligands for the Rh^I-Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron-Deficient Olefins
  作者：Qian Chen、Liang Li、Guangli Zhou、Xiaoli Ma、Lu Zhang、Fang Guo、Yi Luo、Wujiong Xia

  DOI：10.1002/asia.201600143

  日期：2016.5.20

  New chiral phosphorus–olefin hybrid ligands derived from the rigid “privileged” l‐proline have been conveniently prepared and applied in the rhodium‐catalyzed asymmetric arylation of electron‐deficient olefins with arylboronic acids at room temperature; this reaction provides the desired products in excellent yields and high enantioselectivities. The origin of observed stereoselectivity has been investigated

  衍生自刚性“特权” 1-脯氨酸的新型手性磷-烯烃杂化配体已在室温下方便地制备并应用于铑催化的缺电子烯烃与芳基硼酸的不对称芳基化反应。该反应以优异的产率和高对映选择性提供了所需的产物。观察到的立体选择性的起源已通过密度泛函理论（DFT）计算进行了研究。
• Targeting the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 6 (STAT6) with Cell-Permeable, Phosphatase-Stable Phosphopeptide Mimics Potently Inhibits Tyr641 Phosphorylation and Transcriptional Activity
  作者：Pijus K. Mandal、Pietro Morlacchi、J. Morgan Knight、Todd M. Link、Gilbert R. Lee、Roza Nurieva、Divyendu Singh、Ankur Dhanik、Lydia Kavraki、David B. Corry、John E. Ladbury、John S. McMurray

  DOI：10.1021/acs.jmedchem.5b01321

  日期：2015.11.25

  Signal transducer and activator of transcription 6 (STAT6) transmits signals from cytokines IL-4 and IL-13 and is activated in allergic airway disease. We are developing phosphopeptide mimetics targeting the SH2 domain of STAT6 to block recruitment to phosphotyrosine residues on IL-4 or IL-13 receptors and subsequent Tyr641 phosphorylation to inhibit the expression of genes contributing to asthma. Structure-affinity relationship studies showed that phosphopeptides based on Tyr631 from IL-4R alpha bind with weak affinity to STAT6, whereas replacing the pY+3 residue with simple aryl and alkyl amides resulted in affinities in the mid to low nM range. A set of phosphatase-stable, cell-permeable prodrug analogues inhibited cytokine-stimulated STAT6 phosphorylation in both Beas-2B human airway cells and primary mouse T-lymphocytes at concentrations as low as 100 nM. IL-13-stimulated expression of CCL26 (eotaxin-3) was inhibited in a dose-dependent manner, demonstrating that targeting the SH2 domain blocks both phosphorylation and transcriptional activity of STAT6.