6-methoxybenzo[d][1,2,3]triazin-4(3H)-one | 41994-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并-1,2,3-三嗪类化合物
• 英文名称: 6-methoxybenzo[d][1,2,3]triazin-4(3H)-one
• 英文别名: 6-methoxy-3H-1,2,3-benzotriazin-4-one
• CAS: 41994-93-8
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: ZUXOEHFEUPXHJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxybenzo[d][1,2,3]triazin-4(3H)-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯氟甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita

  摘要：

  Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, A2 and A3 showed an excellent nematicidal activity with the inhibition rate of 50.4% and 53.1% at the concentration of 1.0 mg/L, respectively. The influence of substituent type and position was investigated. The relationship between structure and activity was also preliminary analyzed.

  DOI：

  10.1016/j.bmcl.2020.127369
• 作为产物：
  描述：

  5-甲氧基靛红酸酐 在 ammonium carbonate 、 盐酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 6-methoxybenzo[d][1,2,3]triazin-4(3H)-one
  参考文献：
  名称：

  镍催化含烷基腈的 1,2,3-苯并三嗪-4(3H)-酮的分子内双环化反应：获取多种多环喹唑啉酮生物碱的途径

  摘要：

  在此，我们报道了含烷基腈的1,2,3-苯并三嗪-4(3H)-酮的镍催化分子内双环化反应来合成多环喹唑啉酮。该催化反应可以构建多环喹唑啉酮生物碱的核心结构；因此，我们也应用该反应作为获取十五种相关生物碱以证明功效的关键步骤。

  DOI：

  10.1002/adsc.202301512

文献信息

• One-pot synthesis of <i>N</i>-substituted benzannulated triazoles <i>via</i> stable arene diazonium salts
  作者：Rochelle McGrory、Réka J. Faggyas、Andrew Sutherland

  DOI：10.1039/d1ob00968k

  日期：——

  A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts, prepared using a polymer-supported nitrite reagent and p-tosic acid. The transformation was compatible with a wide range

  开发了一种温和有效的一锅法合成 1,2,3-benzotriazin-4(3 H )-ones 和 benzothiatriazine-1,1( 2H )-dioxide 类似物。该方法涉及通过使用聚合物负载的亚硝酸盐试剂和对甲苯磺酸制备的稳定的重氮盐对 2-氨基苯甲酰胺和 2-氨基苯磺酰胺进行重氮化和随后的环化。该转化与多种芳基官能团和酰胺/磺酰胺取代基相容，可用于合成药学上重要的靶标。通过制备含有 1,2,3-benzotriazin-4(3 H )-one的 α-氨基酸，进一步证明了一锅重氮环化过程的合成效用。
• [EN] MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] INHIBITEURS DE MÉTALLOPROTÉINASE MATRICIELLE
  申请人：RANBAXY LAB LTD

  公开号：WO2012038944A1

  公开（公告）日：2012-03-29

  The present invention relates to methyl sulfonamides and N-formamides derivatives of formula (I) and to processes for their syntheses. The invention also relates to pharmacological compositions containing these derivatives and methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatie arthritis, psoriasis, pulmonary fibrosis, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, dry eye, neointimal proliferation which leads to restenosis and ischemic heart failure, stroke, renal disease, tumor metastasis, and other inflammatory disorders characterized by over expression and over activation of an matrix metalloproteinase using the compounds.

  本发明涉及公式（I）的甲基磺酰胺和N-甲酰胺衍生物，以及它们的合成方法。该发明还涉及含有这些衍生物的药物组合物，以及治疗哮喘、类风湿关节炎、慢性阻塞性肺病、鼻炎、骨关节炎、银屑病性关节炎、牛皮癣、肺纤维化、肺部炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、干眼症、新生内膜增生导致再狭窄和缺血性心力衰竭、中风、肾脏疾病、肿瘤转移以及其他以基质金属蛋白酶过度表达和过度活化为特征的炎症性疾病的方法，使用这些化合物。
• 1,2,3-Benzotriazin-4-ones and related systems. Part II. Thermolytic decomposition of substituted 1,2,3-benzotriazin-4-ones and isatoic anhydrides
  作者：John G. Archer、Alan J. Barker、Robert K. Smalley

  DOI：10.1039/p19730001169

  日期：——

  Several nuclear-substituted 1,2,3-benzotriazin-4-ones have been thermolysed in an inert solvent. In each case the major identifiable product proved to be a 2-(o-aminophenyl)-3,1-benzoxazin-4-one. Nuclear-substituted isatoic anhydrides on thermolysis behaved similarly.

  几种核取代的1,2,3-苯并三嗪-4-酮已在惰性溶剂中热解。在每种情况下，主要的可识别产物证明为2-（邻氨基苯基）-3,1-苯并恶嗪-4-酮。核取代的等角酸酐在热解中的表现相似。
• MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Sattigeri Viswajanani J.

  公开号：US20100081610A1

  公开（公告）日：2010-04-01

  The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over-activation of a matrix metalloproteinase using the compounds.

  本发明涉及β-羟基和氨基取代的羧酸，其作为基质金属蛋白酶抑制剂，尤其是对映异构体纯的β-羟基羧酸，以及合成该类化合物和含有本发明化合物的制药组合物的相关过程。本发明化合物在治疗各种炎症、自身免疫和过敏性疾病方面有用，例如治疗哮喘、类风湿性关节炎、慢性阻塞性肺疾病、鼻炎、骨关节炎、银屑病性关节炎、牛皮癣、肺纤维化、创伤愈合障碍、肺炎炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、新内膜增生导致再狭窄和缺血性心力衰竭、中风、肾脏疾病、肿瘤转移以及其他以基质金属蛋白酶过度表达和过度活化为特征的炎症性疾病的方法中使用该化合物。
• Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Aryl Nitrile-Containing 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: A Pathway To Synthesize Luotonin A and Related Polycyclic Pyrroloquinazolinones
  作者：Vijaykumar H. Thorat、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.3c03142

  日期：2023.11.10

  Herein, we report a nickel-catalyzed intramolecular denitrogenative dual annulation reaction of aryl nitrile-containing 1,2,3-benzotriazine-4(3H)-ones to synthesize polycyclic pyrroloquinazolinones with a tolerance of a wide diversity of substituents. This catalytic reaction is the first denitrogenative transannulation of 1,2,3-benzotriazine-4(3H)-one with nitrile, which can be applied as the critical

  在此，我们报道了含芳基腈的1,2,3-苯并三嗪-4(3 H )-酮的镍催化分子内脱氮双环化反应，合成了具有多种取代基的多环吡咯并喹唑啉酮。该催化反应是1,2,3-苯并三嗪-4(3H)-酮与腈的首次脱氮转环反应，可作为合成洛托宁A的关键步骤，具有较高的步骤经济性。