1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile | 1309955-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile
• 英文别名: 1-oxo-3,4-dihydro-2H-isoquinoline-6-carbonitrile；1,2,3,4-tetrahydro-1-oxoisoquinoline-6-carbonitrile；1-Oxo-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile
• CAS: 1309955-19-8
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: KWKIILPTVPFJCV-UHFFFAOYSA-N

物化性质

• 熔点：
  225.4-227.6 °C (decomp)
• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile 在 四溴化碳 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-{5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-1,3,4-oxadiazol-2-yl}-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  TRIAZOLE DERIVATIVE OR SALT THEREOF

  摘要：

  公开号：

  EP2298747B1
• 作为产物：
  描述：

  5-溴茚酮 在 四(三苯基膦)钯 、 sodium azide 作用下， 以 甲烷磺酸 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carbonitrile
  参考文献：
  名称：

  Aromatic ring functionalization of benzolactam derivatives: New potent dopamine D3 receptor ligands

  摘要：

  Since the discovery of the dopamine D-3 receptor, an intensive effort has been directed toward the development of potent and selective ligands in order to elucidate the function and potential therapeutic advantages of targeting D-3 receptors. As a part of our efforts, a novel series of substituted benzolactams derivatives was synthesized mostly through palladium-catalyzed reactions. Their affinities on D-1-D-4 receptors were evaluated and the data led us to highly potent D-3 ligands, some of them highly selective for D-3 receptor, compared to the related dopamine receptor subtypes. Functional D-3 activity assays of the most relevant compounds have been carried out revealing antagonist as well as partial agonist activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.083

文献信息

• Quinoline and Isoquinoline Based HDAC Inhibitors and Methods of Use Thereof
  申请人：Reaction Biology Corp.

  公开号：US20190270733A1

  公开（公告）日：2019-09-05

  The present invention relates to methods of modulating activity of histone deacetylases (HDACs). The present invention also relates to methods of treating HDAC-associated diseases including, but not limited to, cancers, inflammatory disorders, and neurodegenerative disorders. The present invention also provides novel compounds and compositions thereof and methods of preparation of the same. The present invention also includes methods of inhibiting HDACs, and methods of treating HDAC-associated diseases using the compounds of the invention.

  本发明涉及调节组蛋白去乙酰化酶（HDACs）活性的方法。本发明还涉及治疗HDAC相关疾病的方法，包括但不限于癌症、炎症性疾病和神经退行性疾病。本发明还提供了新的化合物及其组合物，以及制备这些化合物和组合物的方法。本发明还包括抑制HDAC的方法，以及使用本发明的化合物治疗HDAC相关疾病的方法。
• 一种苯并[c][1,2]氧杂硼戊环-1(3H)-醇类合物及其用途
  申请人：湖北民族大学

  公开号：CN114149457A

  公开（公告）日：2022-03-08

  本发明公开了一种苯并[c][1,2]氧杂硼戊环‑1(3H)‑醇类其用途，进一步涉及包含所述苯并[c][1,2]氧杂硼戊环‑1(3H)‑醇类合物的药物组合物及其用途；所述苯并[c][1,2]氧杂硼戊环‑1(3H)‑醇类合物或药物组合物可抑制PDE4。本发明提供了一种如式I所示的化合物、其立体异构体、其溶剂合物、其水合物或其药学上可接受的盐。本发明提供的化合物I，其呈现药效活性高、合成步骤简单的优点，具有良好的临床价值和经济价值。
• Rhodium(III)-Catalyzed C–H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds
  作者：Ryan L. Patman、Joyann S. Barber、Dehuan Kong、Wei Li、Indrawan J. McAlpine、Sajiv K. Nair、Sylvie K. Sakata、Nicole Sun

  DOI：10.1055/s-0040-1706548

  日期：2021.1

  feedstock gases enabled through C–H activation. A diverse set of 3,4-dihydroisoquinolones and 3-methylisoquinolones have been prepared in good to excellent yields. The effects of using ethylene and propyne as coupling partners on C–H site selectivity have also been explored with a representative set of substrates and are discussed herein.

  我们描述了通过C–H活化使原料气的Rh（III）催化的[4 + 2]环加成的简单而可靠的过程。已经以良好至优异的产率制备了多种多样的3，4-二氢异喹诺酮和3-甲基异喹诺酮。使用乙烯和丙炔作为偶联伙伴对CH位点选择性的影响也已经在一组代表性的底物上进行了探讨，并在本文中进行了讨论。
• Brain-penetrant cyanoindane and cyanotetralin inhibitors of G2019S-LRRK2 kinase activity
  作者：Albert W. Garofalo、Jacob Schwarz、Kerry Zobel、Claudia Beato、Silvia Bernardi、Federica Budassi、Laura Caberlotto、Peng Gao、Cristiana Griffante、Xinying Liu、Marco Migliore、Feifei Qiao、Fabio Maria Sabbatini、Anna Sava、Mingliang Zhang、Holly J. Carlisle

  DOI：10.1016/j.bmcl.2023.129487

  日期：2023.10

  The G2019S variant of LRRK2, which causes an increase in kinase activity, is associated with the occurrence of Parkinson’s disease (PD). Potent, mutation-selective, and brain penetrant inhibitors of LRRK2 can suppress the biological effects specific to G2019S-LRRK2 that cause pathogenicity. We report the discovery of a series of cyanoindane and cyanotetralin kinase inhibitors culminating in compound

  LRRK2 的 G2019S 变体会导致激酶活性增加，与帕金森病 (PD) 的发生有关。LRRK2 的强效、突变选择性和脑渗透抑制剂可以抑制 G2019S-LRRK2 特有的导致致病性的生物效应。我们报告了一系列氰茚烷和氰四氢萘激酶抑制剂的发现，最终形成化合物34，该化合物显示出对小鼠大脑中 LRRK2 磷酸化的选择性抑制。这些新型抑制剂可能进一步为未来帕金森病治疗开辟精准医疗之路。
• Aromatic ring functionalization of benzolactam derivatives: New potent dopamine D3 receptor ligands
  作者：Raquel Ortega、Harald Hübner、Peter Gmeiner、Christian F. Masaguer

  DOI：10.1016/j.bmcl.2010.12.083

  日期：2011.5

  Since the discovery of the dopamine D-3 receptor, an intensive effort has been directed toward the development of potent and selective ligands in order to elucidate the function and potential therapeutic advantages of targeting D-3 receptors. As a part of our efforts, a novel series of substituted benzolactams derivatives was synthesized mostly through palladium-catalyzed reactions. Their affinities on D-1-D-4 receptors were evaluated and the data led us to highly potent D-3 ligands, some of them highly selective for D-3 receptor, compared to the related dopamine receptor subtypes. Functional D-3 activity assays of the most relevant compounds have been carried out revealing antagonist as well as partial agonist activity. (C) 2010 Elsevier Ltd. All rights reserved.