2-(嘧啶-4-基)乙腈 | 794522-90-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-(嘧啶-4-基)乙腈
• 英文名称: 2-(pyrimidin-4-yl)acetonitrile
• 英文别名: 2-pyrimidin-4-ylacetonitrile
• CAS: 794522-90-0
• 化学式: C₆H₅N₃
• mdl: MFCD17015870
• 分子量: 119.126
• InChiKey: SHHGMESNVFQZIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2-(嘧啶-4-基)乙腈 在 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.5h， 生成 5-[(2-chlorophenyl)acetylamino]-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole
  参考文献：
  名称：

  Design and synthesis of 5-[(2-chloro-6-fluorophenyl)acetylamino]-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole (AKP-001), a novel inhibitor of p38 MAP kinase with reduced side effects based on the antedrug concept

  摘要：

  Inhibitors of p38 mitogen-activated protein (MAP) kinase, which are closely involved in the production of inflammatory cytokines, are considered promising curative drugs for chronic inflammatory disorders. However, there is also a growing concern regarding its systemic side effects. To reduce the occurrence of side effects, we have identified a novel p38 MAP kinase inhibitor that shows properties of an antedrug, which imparts its effect solely on the inflammatory site and is metabolically inactivated right after. We have designed isoxazole derivatives through the addition of a fresh interacting fourth site to the structure of the prototypical p38 MAP kinase inhibitor that harbors three point interactive sites. The derivative 26d (AKP-001) shows excellent p38 MAP kinase inhibitory activity and a high selectivity for various kinases. Its rapid metabolism has been confirmed in rats. Moreover, 26d has been shown to be effective in animal models of inflammatory bowel disease.

  DOI：

  10.1016/j.bmc.2014.05.045
• 作为产物：
  描述：

  4-甲基嘧啶 在 hydroxylamine-O-sulfonic acid 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 2-(嘧啶-4-基)乙腈
  参考文献：
  名称：

  通过用吡啶鎓替代吡啶鎓来调节远红/近红外发射香豆素荧光团中的光稳定性和线粒体选择性。

  摘要：

  线粒体功能障碍与几种人类病理状况有关，包括癌症，衰老和神经退行性疾病。因此，线粒体选择性荧光探针的可用性可能在未来监测细胞功能和疾病进展中起重要作用。在这项工作中，我们研究了如何通过用几个杂环取代对吡啶鎓部分来微调基于非常规香豆素的COUPY荧光团的光物理性质和亚细胞积累。其中，邻，对嘧啶鎓取代为新型荧光团提供了适合生物成像应用的光物理特性，包括从远红外到NIR区域的发射，大的斯托克斯位移和高的光稳定性。此外，与亲本COUPY荧光团相比，该化合物在活细胞中表现出优异的细胞膜通透性，对线粒体的选择性更高。总体而言，这些结果为基于有机小分子的新型线粒体靶向荧光探针的开发提供了有用的见解，因为可以通过用相应的N-烷基化邻位取代常规的N-烷基化吡啶鎓部分来实现对该细胞器的更高选择性。 ，对-pyrimidinium同行。

  DOI：

  10.1021/acs.joc.0c00570

文献信息

• [EN] FTO INHIBITORS<br/>[FR] INHIBITEURS DE FTO
  申请人：NAT INST OF BIOLOGICAL SCIENCES BEIJING

  公开号：WO2016206573A1

  公开（公告）日：2016-12-29

  The invention provides compounds that inhibit FTO (fat mass and obesity), including pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof, particularly obesity, with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  这项发明提供了抑制FTO（脂肪质量和肥胖）的化合物，包括药用可接受的盐、氢化物和立体异构体。这些化合物用于制备药物组合物，以及制备和使用的方法，包括使用有效量的化合物或组合物治疗有需要的人，特别是肥胖症，并检测人的健康或状况的改善。
• [EN] AZOLE METHYLIDENE CYANIDE DERIVATIVES AND THEIR USE AS PROTEIN KINASE MODULATORS<br/>[FR] DERIVES DE CYANURE D'AZOLE METHYLIDENE ET LEUR UTILISATION COMME MODULATEURS DE PROTEINE KINASE
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2003106455A1

  公开（公告）日：2003-12-24

  The present invention is related to azole derivatives notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such azole derivatives. Said azole derivatives are modulators of the protein kinase signalling pathways, particularly the one involving c-Jun N-terminal kinase and/or Glycogen Kinase Synthase 3. The present invention is furthermore related to novel azole derivatives as well as to methods of their preparation. X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1 -C6 alkyl; A is 2-pyridyl, 3-pyridyl, 4-pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group.

  本发明涉及唑衍生物，尤其是用作药物活性化合物的唑衍生物，以及包含这种唑衍生物的药物制剂。所述唑衍生物是蛋白激酶信号通路的调节剂，尤其是涉及c-Jun N端激酶和/或糖原合酶3的那一种。本发明还涉及新颖的唑衍生物以及它们的制备方法。X是O、S或NR0，其中R0是H或未取代或取代的C1-C6烷基；A是2-吡啶基，3-吡啶基，4-吡啶基，吡啶唑基，吡唑啉基，吡嗪基或三嗪基团。
• Synthesis of Bi- and Polyfunctional Isoxazoles from Amino Acid Derived Halogenoximes and Active Methylene Nitriles
  作者：Bohdan A. Chalyk、Kateryna V. Hrebeniuk、Konstantin S. Gavrilenko、Oleh V. Shablykin、Oksana O. Yanshyna、Daniil Bash、Pavel K. Mykhailiuk、Oleksandr S. Liashuk、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.201800311

  日期：2018.6.15

  either an electron‐withdrawing (i.e., CO2Me, CN, or SO2Me) or a heteroaryl group at the α‐position leads to 5‐aminoisoxazoles under basic conditions. The transformation of a malononitrile dimer under analogous conditions has been shown to provide polyfunctional isoxazolo[5,4‐b]pyridine derivatives.

  含有受保护氨基的氯肟与在α位具有吸电子（即CO 2 Me，CN或SO 2 Me）或杂芳基的腈之间的反应在碱性条件下会生成5-氨基异恶唑。已显示丙二腈二聚体在类似条件下的转化可提供多官能异恶唑并[5,4- b ]吡啶衍生物。
• [EN] PYRIDINYL ACETONITRILES<br/>[FR] ACÉTONITRILES DE PYRIDINYLE
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2004098607A1

  公开（公告）日：2004-11-18

  The present invention is related to pyridinyl acetonitriles as well as to pharmaceutical formulations containing such pyridinyl acetonitriles. Said pyridinyl acetonitriles are modulators of the protein kinase signalling pathways, particularly the one involving Glycogen Kinase Synthase 3 or JNK. The present invention is furthermore related to methods of preparing pyridinyl acetonitriles. X is a substituted or unsubstituted pyridinyl. G is an unsubstituted or substituted pyrimidinyl or triazinyl.

  本发明涉及吡啶基乙腈以及含有这种吡啶基乙腈的药物配方。所述吡啶基乙腈是蛋白激酶信号通路的调节剂，特别是涉及糖原激酶合成酶3或JNK的信号通路。本发明还涉及制备吡啶基乙腈的方法。X是取代或未取代的吡啶基。G是未取代或取代的嘧啶基或三嗪基。
• [EN] BENZIMIDAZOLE ACETONITRILES<br/>[FR] BENZOXAZOLE ACÉTONITRILES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005026155A1

  公开（公告）日：2005-03-24

  The present invention is related to benzimidazole acetonitriles as well as to pharmaceutical formulations containing such benzimidazole acetonitriles of formula (I). Said benzimidazole acetonitriles are useful in the treatment of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type II, inadequate glucosetolerance, insulin resistance, obesity, polycystic ovary syndrome (PCOS) (I). The present invention is furthermore related to methods of preparing ben7.oxazole acetonitriles. G is pyrimidinyl; L is an amino group, or a 3-8 membered heterocycloalkyl, containing at least one heteroatorn selected from N, O, S or L is an acylamino moiety; R1 is selected from the group comprising or consisting of hydrogen, sulfonyl, amino, carboxy, aminocarbonyl, CI-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cl-C6-alkoxy, aryl,halogen, cyano or hydroxy;R2 is selected from the group comprising or consisting of hydrogen, CI -C6-alkyl, C2-C6alkenyl, C2-C6-alkynyl, or CI -C6-alkoxy.

  本发明涉及苯并咪唑乙腈，以及含有该苯并咪唑乙腈的药物配方（I）的制备方法。所述苯并咪唑乙腈可用于治疗由胰岛素抵抗或高血糖介导的代谢紊乱，包括糖尿病II型、葡萄糖耐量不良、胰岛素抵抗、肥胖、多囊卵巢综合征（PCOS）。本发明还涉及制备苯7氧唑乙腈的方法。其中G为嘧啶基；L为氨基，或者含有至少一个来自N、O、S的杂原子的3-8成员杂环烷基，或者L为酰氨基基团；R1选自氢、磺酰基、氨基、羧基、氨基甲酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、或者C1-C6烷氧基的群；R2选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、或者C1-C6烷氧基的群。