3-(3-bromopropyl)benzo[d][1,2,3]triazin-4(3H)-one

• 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: 3-(3-bromopropyl)benzo[d][1,2,3]triazin-4(3H)-one
• 英文别名: 3-(3-bromopropyl)-1,2,3-benzotriazin-4(3H)-one；3-(3-bromopropyl)-1,2,3-benzotriazin-4-one
• 化学式: C₁₀H₁₀BrN₃O
• 分子量: 268.113
• InChiKey: QQGYPMITAXMAHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-bromopropyl)benzo[d][1,2,3]triazin-4(3H)-one 在 一水合肼 、 三乙胺 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 二氯氟甲烷 、 N,N-二甲基甲酰胺 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-氨基苯甲酰胺 在 盐酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.92h， 生成 3-(3-bromopropyl)benzo[d][1,2,3]triazin-4(3H)-one
  参考文献：
  名称：

  1,2,3-Benzotriazin-4-one衍生物对根结线虫的合成及杀线虫活性

  摘要：

  通过3-溴烷基-1,2,3-苯并三嗪-4-酮与2-氰基氨基-4-氧噻唑烷的钾盐反应，合成了一系列新的1,2,3-苯并三嗪-4-酮衍生物。碘化钾的存在。杀线虫试验在体内表明，它们中的一些表现出对所造成的黄瓜根结线虫病良好的防治效果南方根结线虫以10.0毫克的L的浓度，最高可达100％-1，表明1,2,3-苯并三-4-one衍生物可能是新型杀线虫剂的潜力。杀线虫活性受分子中取代基类型，取代位置和接头长度的组合影响。浓度为5.0和1.0 mg L –1时的抑制率数据还提供了具有高抑制活性的化合物。当在体外测试时，没有一个对隐孢霉菌有直接抑制作用。体内和体外数据之间显着差异的研究正在进行中。

  DOI：

  10.1021/acs.jafc.5b01762

文献信息

• Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against <i>Meloidogyne incognita</i>
  作者：Gaolei Wang、Xiulei Chen、Yayun Deng、Zhong Li、Xiaoyong Xu

  DOI：10.1021/acs.jafc.5b01762

  日期：2015.8.12

  A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the

  通过3-溴烷基-1,2,3-苯并三嗪-4-酮与2-氰基氨基-4-氧噻唑烷的钾盐反应，合成了一系列新的1,2,3-苯并三嗪-4-酮衍生物。碘化钾的存在。杀线虫试验在体内表明，它们中的一些表现出对所造成的黄瓜根结线虫病良好的防治效果南方根结线虫以10.0毫克的L的浓度，最高可达100％-1，表明1,2,3-苯并三-4-one衍生物可能是新型杀线虫剂的潜力。杀线虫活性受分子中取代基类型，取代位置和接头长度的组合影响。浓度为5.0和1.0 mg L –1时的抑制率数据还提供了具有高抑制活性的化合物。当在体外测试时，没有一个对隐孢霉菌有直接抑制作用。体内和体外数据之间显着差异的研究正在进行中。
• Synthesis of 1,2,3-benzotriazin-4-one derivatives containing spirocyclic indoline-2-one moieties and their nematicidal evaluation
  作者：Gao-Lei Wang、Xi Chen、Ya-Ning Chang、Dan Du、Zhong Li、Xiao-Yong Xu

  DOI：10.1016/j.cclet.2015.10.024

  日期：2015.12

  Abstract To discover new chemotypes of nematicides with proper toxicological profiles, a series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized and further bioevaluated. The bioassay results showed that most of the synthesized compounds were endowed with moderate to good control efficacy against Meloidogyne incognita at 10.0 mg/L in vivo . Among them, compounds 6k and 6p displayed 100%

  摘要为发现具有适当毒理学特征的杀线虫剂的新化学型，合成了一系列新的1,2,3-苯并三嗪-4-酮衍生物，并对其进行了生物评价。生物测定结果表明，在10.0 mg / L的体内，大多数合成化合物对根结线虫有中等到良好的防治作用。其中，化合物6k和6p在此浓度下表现出100％的抑制活性，这意味着它们可用作潜在的杀线虫剂的先导化合物。
• WO2006/117760
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of novel 1,2,3-benzotriazin-4-one derivatives as leukotriene A 4 hydrolase aminopeptidase inhibitors
  作者：Fan Zhang、Dang Wu、Gao-Lei Wang、Shuang Hou、Ping Ou-Yang、Jin Huang、Xiao-Yong Xu

  DOI：10.1016/j.cclet.2016.12.014

  日期：2017.5

  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.
• [EN] ADRENERGIC RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RECEPTEURS ADRENERGIQUES
  申请人：RANBAXY LAB LTD

  公开号：WO2006117760A1

  公开（公告）日：2006-11-09

  [EN] The present invention relates to a_1a and/or a_1b adrenergic receptor antagonists, which can be used to treat a disease or disorder mediated through a_1a and/or a_1b adrenergic receptors. Compounds and pharmaceutical compositions disclosed herein can be used to treat benign prostatic hyperplasia (BPH) and related symptoms thereof. Further, such compounds can be used to treat lower urinary tract symptoms that may or may not be associated with BPH. The present invention also relates to processes to prepare the disclosed compounds, pharmaceutical compositions thereof, and methods of treating BPH or related symptoms thereof.
  [FR] La présente invention concerne des antagonistes des récepteurs adrénergiques la et/ou a^ qui peuvent s'utiliser pour le traitement d'une maladie ou d'un trouble induit par les dits récepteurs adrénergiques. Les composés et compositions de l'invention conviennent pour le traitement de l'hyperplasie bénigne de la prostate (BPH) et symptômes connexes. De tels composés peuvent d'utiliser également pour le traitement de symptômes en rapport avec les voies urinaires inférieures pouvant être ou ne pas être associés à une hyperplasie bénigne de la prostate. De plus, l'invention concerne des procédés de fabrication de ces composés et compositions pharmaceutiques ainsi que des méthodes de traitement de l'hyperplasie bénigne de la prostate et symptômes connexes.