3-phenyl-[1,2,4]triazolo[3,4-a]isoquinoline | 3223-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-[1,2,4]triazolo[3,4-a]isoquinoline
• 英文别名: 3-phenyl-[1,2,4]triazolo[3,4-a]isoquinoline；3-Phenyl-s-triazolo<3,4-a>isochinolin
• CAS: 3223-55-0
• 化学式: C₁₆H₁₁N₃
• 分子量: 245.283
• InChiKey: SKPQAQDIARRMKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iridium(III) acetylacetonate 、 3-phenyl-[1,2,4]triazolo[3,4-a]isoquinoline 以 乙醇 为溶剂， 反应 18.0h， 以15%的产率得到
  参考文献：
  名称：

  TWI520958

  摘要：

  公开号：
• 作为产物：
  描述：

  benzaldehyde isoquinolin-1-ylhydrazone 在 chloroamine-T 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.5h， 以59%的产率得到3-phenyl-[1,2,4]triazolo[3,4-a]isoquinoline
  参考文献：
  名称：

  醛衍生的Hy的钯催化偶联：三唑并吡啶和相关杂环的实用合成

  摘要：

  钯催化的醛衍生的azo酮与氯嗪的分子间偶联，然后在温和的条件下进行氧化环化，可以使用各种各样的双环杂环骨架（参见方案），这些骨架可能会用于药物发现。

  DOI：

  10.1002/anie.201001999

文献信息

• I₂-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition
  作者：Surendra Babu Inturi、Biswajit Kalita、A. Jafar Ahamed

  DOI：10.1039/c6ob01926a

  日期：——

  I2-TBHP-catalyzed azomethine imine generation and subsequent regioselective 1,3-dipolar cycloaddition (DC) with aromatic N-heterocycles was developed to afford various 4,3-fused 1,2,4-triazoles in excellent yields. The method is operationally simple and highly efficient with broad functional group tolerance.

  开发了I 2 -TBHP催化的偶氮甲亚胺亚胺和随后的具有芳香族N-杂环的区域选择性1，3-偶极环加成（DC），以优异的产率提供了各种4，3-稠合的1,2,4-三唑。该方法操作简便且高效，具有宽泛的官能团耐受性。
• Synthesis of 1,2,4-Triazolo[4,3-<i>a</i> ]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization
  作者：Ertong Li、Zhiyuan Hu、Lina Song、Wenquan Yu、Junbiao Chang

  DOI：10.1002/chem.201601744

  日期：2016.7.25

  A facile and efficient approach to access 1,2,4‐triazolo[4,3‐a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine‐mediated oxidative cyclization. This transition‐metal‐free synthetic process is broadly applicable to a variety of aromatic, aliphatic, and α,β‐unsaturated aldehydes, and can

  通过容易获得的芳基肼与相应的醛缩合，然后由碘介导的氧化环化反应，可以轻松而有效地获得1,2,4-三唑并[4,3- a ]吡啶和相关杂环。这种无过渡金属的合成方法广泛适用于各种芳香族，脂肪族和α，β-不饱和醛类，并且可以以克为单位方便地进行。
• The Preparation of 3-Phenyl[1,2,4]triazolo[4,3-<i>a</i>]pyridines and Their Benzologs from<i>N</i>-(Phenylsulfonyl)benzohydrazonoyl Chloride and Pyridines
  作者：Suketaka Ito、Akikazu Kakehi、Toshiyuki Matsuno、Jun-ichi Yoshida

  DOI：10.1246/bcsj.53.2007

  日期：1980.7

  3-Phenyl[1,2,4]triazolo[4,3-a]pyridines were obtained in good yields from N′-[α-(1-pyridinio)benzylidene]benzenesulfonohydrazidates, generated from 2-unsubstituted pyridines and N-(phenylsulfonyl)benzohydrazonoyl chloride (2), by oxidation with chloranil. The reaction of quinoline and isoquinoline with 2 gave 1-phenyl-3-phenylsulfonyl-3,3a-dihydro[1,2,4] triazolo [4,3-a]quinoline and 3-phenyl-1-phenylsulfonyl-1

  3-苯基[1,2,4]三唑并[4,3-a]吡啶以良好的收率从N'-[α-(1-吡啶基)苄叉]苯磺酰肼中获得，由2-未取代的吡啶和N-(苯磺酰基）苯并腙酰氯（2），用氯苯醌氧化。喹啉和异喹啉与 2 反应得到 1-苯基-3-苯基磺酰基-3,3a-二氢[1,2,4]三唑并[4,3-a]喹啉和3-苯基-1-苯基磺酰基-1,10b -二氢[1,2,4]三唑并[3,4-a]异喹啉，均产率良好；它们在加热时通过苯亚磺酸的 1,2-消除芳构化为相应的三唑。
• Pharmaceutical use of fused 1,2,4-triazoles
  申请人：Andersen Sune Henrik

  公开号：US20060106008A1

  公开（公告）日：2006-05-18

  The use of fused 1,2,4-triazoles for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions has been described. Also a novel class of fused 1,2,4-triazoles, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments has been described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  使用熔合的1,2,4-三唑类物质来调节11β-羟基类固醇脱氢酶1型（11βHSD1）的活性以及将这些化合物用作制药组合物已经被描述。同时，还描述了一种新的熔合的1,2,4-三唑类物质，它们在治疗中的使用、包含这些化合物的制药组合物以及它们在制造药物方面的使用。这些化合物是调节剂，更具体地说是11βHSD1的抑制剂，可能在治疗、预防和/或预防一系列医学疾病中有用，其中需要降低细胞内活性糖皮质激素的浓度。
• Pharmaceutical Use of Fused 1,2,4-Triazoles
  申请人：Andersen Henrik Sune

  公开号：US20080153807A1

  公开（公告）日：2008-06-26

  The use of fused 1,2,4-triazoles for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions has been described. Also a novel class of fused 1,2,4-triazoles, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments has been described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  使用熔合的1,2,4-三唑类化合物来调节11β-羟基类固醇脱氢酶1型（11βHSD1）的活性，并将这些化合物用作制药组合物的用途已经被描述。同时，还描述了一种新型的熔合的1,2,4-三唑类化合物，它们在治疗中的应用、包含这些化合物的制药组合物，以及它们在制造药物方面的用途。这些化合物是调节剂，更具体地说是11βHSD1的抑制剂，并可用于治疗、预防和/或预防一系列医学疾病，其中需要降低细胞内活性糖皮质激素的浓度。