3-(2-chloroethyl)-1,2,3-benzotriazin-4(3H)-one | 10090-01-4

• 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-(2-chloroethyl)-1,2,3-benzotriazin-4(3H)-one
• 英文别名: 3-(2-Chloroethyl)-1,2,3-benzotriazin-4-one
• CAS: 10090-01-4
• 化学式: C₉H₈ClN₃O
• 分子量: 209.635
• InChiKey: NBHISPQLWAMUIN-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C(Solv: methanol (67-56-1))
• 沸点：
  339.5±44.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-苄基哌嗪 、 3-(2-chloroethyl)-1,2,3-benzotriazin-4(3H)-one 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以92%的产率得到
  参考文献：
  名称：

  Synthesis by microwave irradiation and binding properties of novel 5-HT1A receptor ligands

  摘要：

  This work reports the synthesis by microwave irradiation and the binding tests on the 5-HT1A, 5-HT2A and 5-HT2C receptors of new substituted piperazines in order to identify selective ligands for 5-HT1A subtype receptor. Conventional heating and microwave irradiation of the reactions was compared. Synthesis by microwave irradiation gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. Some resulting active compounds (29 and 39) were characterised by a good selectivity profile for the 5-HT1A subtype receptor. The more active compounds were selected and further evaluated for their binding affinities on D-1, D-2 dopaminergic and alpha(1), alpha(2) adrenergic receptors. The compound with higher affinity and selectivity for the 5-HT1A over all the considered receptors was the 3-{4-[4-(1,2,3,4-tetrahydronaplithyl)-1-piperazinyl]butan}-benzotriazinone (-)29 (5-HT1A K-i = 36 nM, other receptors not active). (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01287-9
• 作为产物：
  描述：

  以 乙醇 为溶剂， 生成 3-(2-chloroethyl)-1,2,3-benzotriazin-4(3H)-one
  参考文献：
  名称：

  一系列苯并三嗪酮和相关抗肿瘤杂环的 A15N NMR 研究

  摘要：

  通过标准方法合成了一系列 3-取代的 1,2,3-苯并三嗪-4-酮，1 和 2，并记录了 15N NMR 光谱。所有光谱均使用氮 15 同位素的天然丰度获得。三嗪环的 N-1、N-2 和 N-3 的化学位移出现在正常范围内，并且还与咪唑并三嗪酮 4 和咪唑并四嗪酮 5 光谱中的化学位移相关。 1a、2 和 4 的光谱，用完整的 NOE 记录，显示分配给 N-3 的单线态的反转，证明这些化合物以所示的互变异构形式存在。15N NMR 分析证实了 4-亚氨基苯并三嗪酮 (3) 的结构。光谱显示了带有 NH 的亚氨基氮原子的信号，它是 NOE 光谱中的倒置单线态，而来自 3 的 N-3 原子的信号在 NOE 光谱中没有反转。版权所有 © 2002 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.994

文献信息

• Synthesis andIn-vitroPharmacological Evaluation of New 5-HT1AReceptor Ligands Containing a Benzotriazinone Nucleus
  作者：Ferdinando Fiorino、Beatrice Severino、Francesca De Angelis、Elisa Perissutti、Francesco Frecentese、Paola Massarelli、Giancarlo Bruni、Elga Collavoli、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1002/ardp.200700151

  日期：2008.1

  were selected and further evaluated for their binding affinities on D1, D2 dopaminergic and α1, α2 adrenergic receptors. The 3‐(2‐(4‐(naphthalen‐1‐yl)piperazin‐1‐yl)ethyl)benzo[d][1,2,3]triazin‐4(3H)‐one 5 with Ki = 0.000178 nM was the most active and selective derivative for the 5‐HT1A receptor with respect to other serotonin receptors and the most selective derivative compared to dopaminergic and

  本文报道了新型苯并三嗪酮衍生物的5-HT1A、5-HT2A和5-HT2C受体的微波辅助合成和结合分析，以鉴定5-HT1A亚型受体的选择性配体。对反应的常规加热和微波加热进行了比较。良好的收率和较短的反应时间是我们合成路线的主要优势。选择了更多活性化合物，并进一步评估了它们对 D1、D2 多巴胺能受体和 α1、α2 肾上腺素能受体的结合亲和力。Ki = 0.000178 nM 的 3- (2- (4- (naphthalen - 1 - yl) piperazin - 1 - yl) 乙基) 苯并 [d] [1,2,3] 三嗪 - 4 (3H) -one 5 是5-HT1A 受体相对于其他血清素受体的活性和选择性最强的衍生物，与多巴胺能和肾上腺素能受体相比，选择性最强的衍生物。
• Synthesis by Microwave Irradiation and Antidiarrhoeal Activity of Benzotriazinone and Saccharine Derivatives
  作者：Ferdinando Fiorino、Giuseppe Caliendo、Elisa Perissutti、Beatrice Severino、Francesco Frecentese、Barbara Preziosi、Angelo A. Izzo、Raffaele Capasso、Vincenzo Santagada

  DOI：10.1002/ardp.200500134

  日期：2005.11

  The synthesis by microwave irradiation and the biological results of novel benzotriazinone and saccharine derivatives with potential antidiarrhoeal activity is described. Conventional and microwave heatings were compared for the reactions. Good yields and short reaction times are the main advantages of our synthetic route. Among the tested compounds, compound 12 inhibited motility both in in‐vitro

  描述了具有潜在止泻活性的新型苯并三嗪酮和糖精衍生物的微波辐射合成和生物学结果。比较了常规加热和微波加热的反应。良好的收率和较短的反应时间是我们合成路线的主要优势。在测试的化合物中，化合物 12 在体外和体内测试中均抑制运动。
• 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
• FERRAND, GERARD;DUMAS, HERVE;DEPIN, JEAN-CLAUDE;CHAVERNAC, GILLES, EUR. J. MED. CHEM., 22,(1987) N 4, 337-345
  作者：FERRAND, GERARD、DUMAS, HERVE、DEPIN, JEAN-CLAUDE、CHAVERNAC, GILLES

  DOI：——

  日期：——
• Synthesis by microwave irradiation and binding properties of novel 5-HT1A receptor ligands
  作者：G Caliendo

  DOI：10.1016/s0223-5234(01)01287-9

  日期：2001.12.1

  This work reports the synthesis by microwave irradiation and the binding tests on the 5-HT1A, 5-HT2A and 5-HT2C receptors of new substituted piperazines in order to identify selective ligands for 5-HT1A subtype receptor. Conventional heating and microwave irradiation of the reactions was compared. Synthesis by microwave irradiation gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. Some resulting active compounds (29 and 39) were characterised by a good selectivity profile for the 5-HT1A subtype receptor. The more active compounds were selected and further evaluated for their binding affinities on D-1, D-2 dopaminergic and alpha(1), alpha(2) adrenergic receptors. The compound with higher affinity and selectivity for the 5-HT1A over all the considered receptors was the 3-4-[4-(1,2,3,4-tetrahydronaplithyl)-1-piperazinyl]butan}-benzotriazinone (-)29 (5-HT1A K-i = 36 nM, other receptors not active). (C) 2001 Editions scientifiques et medicales Elsevier SAS.