8-chloro-3H-benzo[d][1,2,3]triazin-4-one | 18343-45-8

• 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: 8-chloro-3H-benzo[d][1,2,3]triazin-4-one
• 英文别名: 8-chloro-3H-benzo[d][1,2,3]triazin-4-one；8-chloro-3H-1,2,3-benzotriazin-4-one
• CAS: 18343-45-8
• 化学式: C₇H₄ClN₃O
• 分子量: 181.581
• InChiKey: RRLGSAHSYQVYED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-chloro-3H-benzo[d][1,2,3]triazin-4-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：

  2-氨基-3-氯苯甲酰胺 在 盐酸 、 sodium nitrite 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.5h， 生成 8-chloro-3H-benzo[d][1,2,3]triazin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A 4 hydrolase aminopeptidase inhibitors

  摘要：

  A series of novel 1,2,3-benzotriazin-4-one derivatives were designed, synthesized and their inhibitory activities against leukotriene A(4) hydrolase aminopeptidase in vitro were evaluated. Many compounds showed moderate to good activities at the concentration of 10 mu mol/L. Among them, compound IV-16 exhibited the highest inhibitory activity up to 80.6% with an IC50 of 1.30 +/- 0.20 mu mol/L. The compound IV-16 was also tested the proliferation inhibitory activities in THP1 human AML cell line and its binding model with LTA(4)H enzyme by molecular docking was studied. It indicated that 1,2,3-benzotriazin-4-one was a promising scaffold for further study. The relationship between structure and inhibitory activity was also preliminarily discussed. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2016.12.014

文献信息

• 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。
• Matrix metalloproteinase inhibitors
  申请人：Ranbaxy Laboratories Limited

  公开号：EP2322507A1

  公开（公告）日：2011-05-18

  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.

  本发明涉及作为基质金属蛋白酶抑制剂的β-羟基和氨基取代的羧酸，特别是非对映异构纯的β-羟基羧酸，以及合成本发明化合物的相应工艺和含有本发明化合物的药物组合物。本发明的化合物可用于治疗各种炎症、自身免疫性和过敏性疾病，如治疗哮喘、类风湿性关节炎、慢性阻塞性肺病、鼻炎、骨关节炎、银屑病关节炎、牛皮癣、肺纤维化、伤口愈合障碍、肺部炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、多发性骨髓瘤、多发性硬化症、多发性硬化症的方法、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、导致再狭窄和缺血性心力衰竭的新内膜增生、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激活为特征的炎症性疾病。
• [EN] TRIAZINE HETEROCYCLIC COMPOUND WITH NEMATICIDAL ACTIVITY AND PREPARATION METHOD THEREFOR AND USAGE THEREOF<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE DE TRIAZINE AYANT UNE ACTIVITÉ NÉMATICIDE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 一种具有杀线虫活性的三嗪杂环化合物及其制法和用途
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2016116058A1

  公开（公告）日：2016-07-28

  本发明涉及一种具有杀线虫活性的三嗪杂环化合物及其制法和用途。具体地，本发明公开了具有式(I)化合物或其光学异构体、顺反异构体或农药学上可接受的盐，及其制备方法。本发明还公开了包含上述化合物的农用组合物及其用途。上述化合物具有优异的杀线虫活性。
• Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita
  作者：Xiulei Chen、Haowu Jia、Zhong Li、Xiaoyong Xu

  DOI：10.1016/j.cclet.2019.02.033

  日期：2019.6

  To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Synthèse et activité anti-dépressive potentielle de nouvelles triazine-1,2,3 ones-4
  作者：Gérard Ferrand、Hervé Dumas、Jean-Claude Depin、Gilles Chavernac

  DOI：10.1016/0223-5234(87)90272-8

  日期：1987.7