(2S)-吡咯烷-2-腈三氟乙酸盐 | 473797-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S)-吡咯烷-2-腈三氟乙酸盐
• 英文名称: 2(S)-cyanopyrrolidine trifluoroacetic acid salt
• 英文别名: (S)-pyrrolidine-2-carbonitrile trifluoroacetate；(2S)-pyrrolidine-2-carbonitrile trifluoroacetate；(2S)-pyrrolidine-2-carbonitrile;2,2,2-trifluoroacetic acid
• CAS: 473797-71-6
• 化学式: C₂HF₃O₂*C₅H₈N₂
• 分子量: 210.156
• InChiKey: QROMHLFLMYDBEQ-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-吡咯烷-2-腈三氟乙酸盐 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到(S)-吡咯烷-2-腈
  参考文献：
  名称：

  氨基腈和氨基甲酸酯作为有机催化剂在醛醇缩合反应中的评价

  摘要：

  抽象的 的效率升-缬氨酸和升-脯氨酸腈和叔丁基升-脯氨酸亚氨酸酯作为醛醇缩合反应的有机催化剂进行了评价。升缬氨酸腈被发现是一个SYN -选择性催化剂，而升脯氨酸腈被认为是抗体选择性，并给了产品在适度良好的对映选择性。叔丁基升-proline亚胺酯被发现是在起始试剂产品的转化率来表示一个非常有效的催化剂，并得到良好的抗-选择性。叔丁基的对映选择性升-脯氨酸亚氨酸酯被认为是卓越的，与形成在高达94％的对映体过量的产品。 的效率升-缬氨酸和升-脯氨酸腈和叔丁基升-脯氨酸亚氨酸酯作为醛醇缩合反应的有机催化剂进行了评价。升缬氨酸腈被发现是一个SYN -选择性催化剂，而升脯氨酸腈被认为是抗体选择性，并给了产品在适度良好的对映选择性。叔丁基升-proline亚胺酯被发现是在起始试剂产品的转化率来表示一个非常有效的催化剂，并得到良好的抗-选择性。叔丁基的对映选择性升-脯氨酸亚氨酸酯被认为是卓越的，与形成在高达94％的对映体过量的产品。

  DOI：

  10.1055/s-0039-1690150
• 作为产物：
  描述：

  D-脯氨酸 在 2,4,6-三甲基吡啶 、 三聚氯氰 、 sodium carbonate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 (2S)-吡咯烷-2-腈三氟乙酸盐
  参考文献：
  名称：

  Development of Amidine-Based Sphingosine Kinase 1 Nanomolar Inhibitors and Reduction of Sphingosine 1-Phosphate in Human Leukemia Cells

  摘要：

  Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

  DOI：

  10.1021/jm2001053

文献信息

• Modular syntheses of oxazolinylamine ligands and characterization of group 10 metal complexes
  作者：Christine A Caputo、Florentino d S Carneiro、Michael C Jennings、Nathan D Jones

  DOI：10.1139/v06-188

  日期：2007.2.1

  The syntheses of aminoalkyloxazoline and pyrrolidinyloxazoline ligands, each of which bear a pair of chiral centres, by both known and new routes are reported. Variable temperature NMR studies show that the known stepwise syntheses of the pyrrolidinyl compounds are not complicated by epimerization; however, coordination of one of the aminoalkyl derivatives to Pt(II) under conditions of prolonged heating to 80 °C does give mixtures of diastereomeric N,N ′-chelated complexes that result from inversion of the chiral centre associated with the aminoalkyl fragment. A new synthesis of pyrrolidinyloxazoline ligands that involves the Zn-catalyzed cyclization of Cbz-protected 2-cyanopyrrolidine and β-amino alcohols is also reported. This procedure offers the advantages of economy, shorter time, and fewer purification steps over the previously reported synthesis. In addition, the crystal structure of an enantiopure Pd(II) complex of an N,N ′-chelated pyrrolidinyloxazoline is disclosed. This compound has a pseudo-C₂ axis of symmetry, which may make it suitable for asymmetric catalytic applications.Key words: chiral ligands, ligand design, oxazolines, variable temperature NMR spectroscopy, asymmetric catalysis, coordination compounds, palladium, platinum

  报告采用已知路线和新路线合成了氨基烷基恶唑啉和吡咯烷基恶唑啉配体，每种配体都带有一对手性中心。变温核磁共振研究表明，已知的吡咯烷基化合物的逐步合成过程不会因表聚而复杂化；然而，在长时间加热至 80 °C 的条件下，将其中一种氨基烷基衍生物与 Pt(II) 配位，确实会产生非对映的 N,N′-螯合复合物混合物，这是因为与氨基烷基片段相关的手性中心发生了反转。此外，还报道了一种吡咯烷基噁唑啉配体的新合成方法，该方法涉及 Zn 催化的 Cbz 保护的 2-氰基吡咯烷和 β-氨基醇的环化。与之前报道的合成方法相比，该方法具有经济、时间短、纯化步骤少等优点。此外，还公开了一种 N,N′-螯合吡咯烷基噁唑啉的对映体纯 Pd(II) 复合物的晶体结构。关键词：手性配体；配体设计；噁唑啉；变温核磁共振光谱；不对称催化；配位化合物；钯；铂
• [EN] 2-CYANOPYRROLES AND THEIR ANALOGUES AS DDP-IV INHIBITORS<br/>[FR] 2-CYANOPYRROLES ET LEURS ANALOGUES EN TANT QU'INHIBITEURS DE DIPEPTIDYLPEPTIDASE-IV (DP-IV)
  申请人：NOVO NORDISK AS

  公开号：WO2004089362A1

  公开（公告）日：2004-10-21

  The present invention relates to therapeutically active and selective inhibitors of the enzyme DPP-IV having the formula I: (I) The invention furthermore relates to pharmaceutical compositions comprising the compounds and the use of such compounds for the manufacture of medicaments for treating diseases that are associated with proteins which are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity.

  本发明涉及具有以下式I的治疗活性和选择性抑制剂的酶DPP-IV。此外，本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物制造用于治疗与DPP-IV使蛋白质失活相关的疾病的药物，例如2型糖尿病和肥胖症。
• [EN] FACTOR XIIA INHIBITORS<br/>[FR] INHIBITEURS DU FACTEUR XIIA
  申请人：UNIV LEEDS INNOVATIONS LTD

  公开号：WO2019186164A1

  公开（公告）日：2019-10-03

  This invention relates to compoundsof formula (I)and methods of treatment using the compounds. The invention also relates to processes and methods for producing the compounds of the invention. The compounds of the invention are modulators of Factor XII (e.g. Factor XIIa). In particular, the compounds are inhibitors of Factor XIIa and may be useful as anticoagulants.

  本发明涉及公式(I)的化合物以及使用这些化合物进行治疗的方法。该发明还涉及用于生产该发明化合物的过程和方法。该发明化合物是凝血因子XII（例如凝血因子XIIa）的调节剂。具体来说，这些化合物是凝血因子XIIa的抑制剂，可能作为抗凝血剂有用。
• Geometry-Retentive C-Alkenylation of Lithiated α-Aminonitriles: Quaternary α-Alkenyl Amino Acids and Hydantoins
  作者：Josep Mas-Roselló、Shuji Hachisu、Jonathan Clayden

  DOI：10.1002/anie.201704908

  日期：2017.8.28

  from the same N-allyl precursor by stereodivergent alkene isomerization. The reaction, formally a nucleophilic substitution at an sp2 carbon atom, allows the direct regioselective incorporation of mono-, di-, tri-, and tetrasubstituted olefins at the α-carbon of amino acid derivatives. The initially formed 5-alkenyl iminohydantoins may be hydrolyzed and oxidatively deprotected to yield hydantoins and unsaturated

  通过尿素键束缚到烯烃上的α-氨基腈在碱处理下，通过锂腈衍生物对N'-烯基的攻击而进行分子内C-烯基化。保留几何构型的烯烃移位从对应的起始E-或Z - N'-链烯基脲立体定向地提供了5-链烯基-4-亚氨基乙内酰脲产品的E或Z异构体，它们各自可以由相同的N-烯丙基形成前体通过立体发散的烯烃异构化。该反应是在sp 2上的亲核取代碳原子允许在氨基酸衍生物的α-碳上直接区域选择性地引入单，二，三和四取代的烯烃。最初形成的5-烯基亚氨基乙内酰脲可以被水解和氧化脱保护以产生乙内酰脲和不饱和α-季氨基酸。
• [EN] COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY, METHODS FOR THEIR PREPARATION AND THEIR USE<br/>[FR] COMPOSES INHIBITEURS DE LA PROLYL OLIGOPEPTIDASE, PROCEDES DE PREPARATION ET UTILISATION
  申请人：ORION CORP

  公开号：WO2003004468A1

  公开（公告）日：2003-01-16

  Compounds of the formula (I), wherein the symbol aa means a residue of an α-amino acid. The invention is also directed to a method for the preparation of the compounds of formula (I), as well as their use as prolyl oligopeptide inhibitors, for example for the treatment of Alzheimer's disease.

  公式（I）的化合物，其中符号aa表示α-氨基酸的残基。本发明还涉及一种制备公式（I）化合物的方法，以及它们作为脯氨酰寡肽抑制剂的用途，例如用于治疗阿尔茨海默病。