6-(1,3-苯并二氧杂环戊-5-基)-2-吡啶甲醛 | 834884-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 6-(1,3-苯并二氧杂环戊-5-基)-2-吡啶甲醛
• 中文别名: 6-(1,3-苯并二氧代l-5-基)-2-吡啶羧醛；6-(苯并[1,3]二氧杂-5-基)吡啶-2-甲醛
• 英文名称: 6-(benzo[d][1,3]dioxol-5-yl)-2-formylpyridine
• 英文别名: 6-(1,3-benzodioxal-5-yl)-2-pyridinecarboxaldehyde；6-(1,3-benzodioxol-5-yl)-2-pyridinecarbaldehyde；6-(benzo[d][1,3]dioxol-5-yl)picolinaldehyde；6-(1,3-Benzodioxol-5-yl)-2-pyridinecarboxaldehyde；6-(1,3-benzodioxol-5-yl)pyridine-2-carbaldehyde
• CAS: 834884-78-5
• 化学式: C₁₃H₉NO₃
• 分子量: 227.219
• InChiKey: XITSUEJTFNGOIW-UHFFFAOYSA-N

物化性质

• 熔点：
  117-122 °C
• 沸点：
  391.6±42.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S36

反应信息

• 作为反应物：
  描述：

  6-(1,3-苯并二氧杂环戊-5-基)-2-吡啶甲醛 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  使用发光席夫碱对Cr3 +和Al3 +进行双传感和同步荧光光谱监测：萃取和DFT研究。

  摘要：

  通过1-氨基new与6-（1,3-苯并二氧杂-5-基）-2-吡啶甲醛的1：1缩合反应合成了设计良好的新型pyr基小分子（L），其特征在于吸收，发射光谱，FTIR，NMR和质谱研究。有趣的是，紫外可见光谱和荧光光谱研究表明，配体（L）可作为水性环境中铬（III）（Cr3 +）和铝（III）（Al3 +）的双开启发光化学传感器。和TDDFT研究。L在存在Cr3 +和Al3 +的情况下显示出从浅黄色到红黄色的显着颜色变化，检测极限为〜10-9 M，而在其他一价和二价金属离子的存在下没有明显的变化。Cr3 +，Al3 +，将Fe3 +和EDTA与基于4个输入逻辑门的高级组合INHIBIT门进行了比较。在此，使用一阶导数恒定波长同步荧光光谱法（1st DCWSFS）通过增加各个重叠峰的光谱分辨率来确定混合物中的Cr3 +，Al3 +离子浓度。据报道，第一种DCWSFS用于药物中，但是在没有事先分离的

  DOI：

  10.1016/j.saa.2019.117837

文献信息

• Aminopyrimidine Kinase Inhibitors
  申请人：Baldino Carmen M.

  公开号：US20110152235A1

  公开（公告）日：2011-06-23

  Disclosed are compounds, pharmaceutical compositions containing those compounds, and uses of the compounds and compositions as modulators of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway. Uses are also disclosed for the treatment or prevention of a range of therapeutic indications due at least in part to aberrant physiological activity of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway.

  揭示了化合物、含有这些化合物的药物组合物，以及这些化合物和组合物作为酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径调节剂的用途。还揭示了用于治疗或预防一系列治疗适应症的用途，至少部分原因是由于酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径的异常生理活性。
• Design and Microwave Synthesis of New (5Z) 5-Arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5Z) 2-Amino-5-arylidene-1,3-thiazol-4(5H)-one as New Inhibitors of Protein Kinase DYRK1A
  作者：Khadidja Bourahla、Solène Guihéneuf、Emmanuelle Limanton、Ludovic Paquin、Rémy Le Guével、Thierry Charlier、Mustapha Rahmouni、Emilie Durieu、Olivier Lozach、François Carreaux、Laurent Meijer、Jean-Pierre Bazureau

  DOI：10.3390/ph14111086

  日期：——

  Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradiation. The 46 designed final compounds were tested in order to determine their activity against four representative protein kinases (DYR1A, CK1, CDK5/p25, and GSK3α/β). Among these 1,3-thiazolidin-4-ones, the molecules (5Z) 5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 3e (IC50 0.028 μM) and (5Z)-5-benzo[1,3]dioxol-5-ylmethylene-2-(pyridin-2-yl)amino-1,3-thiazol-4(5H)-one 5s (IC50 0.033 μM) were identified as lead compounds and as new nanomolar DYRK1A inhibitors. Some of these compounds in the two libraries have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT 116, PC3, and NCI-H2 tumor cell lines). These results will enable us to use the 1,3-thiazolidin-4-one core as pharmacophores to develop potent treatment for neurological or oncological disorders in which DYRK1A is fully involved.

  在这里，我们报道了在微波辐射下合成了新的5-芳基亚基-2-硫代-1,3-噻唑啉-4-酮3类（二十二个化合物）和新的2-氨基-5-芳基亚基-1,3-噻唑-4（5H）-酮5类（二十四个化合物），具有立体控制的Z-几何构型。设计的46个最终化合物被测试，以确定它们对四种代表性蛋白激酶（DYR1A、CK1、CDK5/p25和GSK3α/β）的活性。在这些1,3-噻唑啉-4-酮中，分子（5Z）5-（4-羟基苯基亚基）-2-硫代-1,3-噻唑啉-4-酮3e（IC50为0.028μM）和（5Z）-5-苯并[1,3]二氧杂环-5-基亚甲基-2-（吡啶-2-基）氨基-1,3-噻唑-4（5H）-酮5s（IC50为0.033μM）被确定为引物化合物和新的纳摩尔级DYRK1A抑制剂。这两个库中的一些化合物也已评估其对细胞增殖的体外抑制作用（Huh7 D12、Caco2、MDA-MB 231、HCT 116、PC3和NCI-H2肿瘤细胞系）。这些结果将使我们能够利用1,3-噻唑啉-4-酮核作为药效团，开发用于治疗DYRK1A完全参与的神经或肿瘤疾病的有效治疗方法。
• AMINOPYRIMIDINE KINASE INHIBITORS
  申请人：Jasco Pharmaceuticals, LLC

  公开号：US20150202205A1

  公开（公告）日：2015-07-23

  Disclosed are compounds, pharmaceutical compositions containing those compounds, and uses of the compounds and compositions as modulators of CK1, CK1γ1, CK1γ2, CK1γ3, CK2, Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, the AKT pathway, and/or the mTOR pathway. Uses are also disclosed for the treatment or prevention of a range of therapeutic indications due at least in part to aberrant physiological activity of CK1, CK1γ1, CK1γ2, CK1γ3, CK2, Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, the AKT pathway, and/or the mTOR pathway.

  本发明涉及化合物、含有这些化合物的制药组合物，以及这些化合物和组合物作为CK1、CK1γ1、CK1γ2、CK1γ3、CK2、Pim1、Pim2、Pim3、TGFβ通路、Wnt通路、JAK/STAT通路、AKT通路和/或mTOR通路的调节剂的用途。本发明还涉及用于治疗或预防由于CK1、CK1γ1、CK1γ2、CK1γ3、CK2、Pim1、Pim2、Pim3、TGFβ通路、Wnt通路、JAK/STAT通路、AKT通路和/或mTOR通路异常生理活性引起的一系列治疗适应症的用途。
• Aminopyrimidine kinase inhibitors
  申请人：Jasco Pharmaceuticals, LLC

  公开号：US10336743B2

  公开（公告）日：2019-07-02

  Disclosed are compounds, pharmaceutical compositions containing those compounds, and uses of the compounds and compositions as modulators of CK1, CK1γ1, CK1γ2, CK1γ3, CK2, Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, the AKT pathway, and/or the mTOR pathway. Uses are also disclosed for the treatment or prevention of a range of therapeutic indications due at least in part to aberrant physiological activity of CK1, CK1γ1, CK1γ2, CK1γ3, CK2, Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, the AKT pathway, and/or the mTOR pathway.

  公开了化合物、含有这些化合物的药物组合物，以及这些化合物和组合物作为CK1、CK1γ1、CK1γ2、CK1γ3、CK2、Pim 1、Pim2、Pim3、TGFβ通路、Wnt通路、JAK/STAT通路、AKT通路和/或mTOR通路调节剂的用途。还公开了用于治疗或预防至少部分由 CK1、CK1γ1、CK1γ2、CK1γ3、CK2、Pim 1、Pim2、Pim3、TGFβ 通路、Wnt 通路、JAK/STAT 通路、AKT 通路和/或 mTOR 通路的异常生理活性引起的一系列治疗适应症的用途。
• Cyclooxygenase-1-Selective Inhibitors Based on the (<i>E</i>)-2′-<i>Des</i>-methyl-sulindac Sulfide Scaffold
  作者：Andy J. Liedtke、Brenda C. Crews、Cristina M. Daniel、Anna L. Blobaum、Philip J. Kingsley、Kebreab Ghebreselasie、Lawrence J. Marnett

  DOI：10.1021/jm201528b

  日期：2012.3.8

  Prostaglandins (PGs) are powerful lipid mediators in many physiological and pathophysiological responses. They are produced by oxidation of arachidonic acid (AA) by cyclo- oxygenases (COX-1 and COX-2) followed by metabolism of endoperoidde intermediates by terminal PG synthases. PG biosynthesis is inhibited by nonsteroidal anti-inflammatory drugs (NSAIDs). Specific inhibition of COX-2 has been extensively investigated, but relatively few COX-1-selective inhibitors have been described. Recent reports of a possible contribution of COX-1 in analgesia, neuroinflammation, or carcinogenesis suggest that COX-1 is a potential therapeutic target. We designed, synthesized, and evaluated a series of (E)-2'-des-methyl-sulindac sulfide (E-DMSS) analogues for inhibition of COX-1. Several potent and selective inhibitors were discovered, and the most promising compounds were active against COX-1 in intact ovarian carcinoma cells (OVCAR-3). The compounds inhibited tumor cell proliferation but only at concentrations >100-fold higher than the concentrations that inhibit COX-1 activity. E-DMSS analogues may be useful probes of COX-1 biology in vivo and promising leads for COX-1-targeted therapeutic agents.