3-(3-chloropropoxy)-1,2,3-benzotriazin-4(3H)-one | 434339-52-3

• 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-chloropropoxy)-1,2,3-benzotriazin-4(3H)-one
• 英文别名: 3-(3-Chloropropoxy)-1,2,3-benzotriazin-4-one
• CAS: 434339-52-3
• 化学式: C₁₀H₁₀ClN₃O₂
• 分子量: 239.661
• InChiKey: PZFXWPZUVTZLCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苄基哌嗪 、 3-(3-chloropropoxy)-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85%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：

  1-溴-3-氯丙烷 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以94%的产率得到3-(3-chloropropoxy)-1,2,3-benzotriazin-4(3H)-one
  参考文献：
  名称：

  苯并三嗪酮和糖精衍生物的微波辐射合成及止泻活性

  摘要：

  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。

  DOI：

  10.1002/ardp.200500134

文献信息

• 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。
• 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.
• Synthesis of 1-naphtylpiperazine derivatives as serotoninergic ligands and their evaluation as antiproliferative agents
  作者：Ferdinando Fiorino、Elisa Magli、Elisa Perissutti、Beatrice Severino、Francesco Frecentese、Antonella Esposito、Francesca De Angelis、Giuseppina Maria Incisivo、Paola Massarelli、Cristina Nencini、Elena Di Gennaro、Alfredo Budillon、Alessandra Di Cintio、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1016/j.ejmech.2011.03.001

  日期：2011.6

  investigate on potential use of 5-HT1A ligands as antiproliferative agents, we have analyzed a new set of 1-naphtylpiperazine derivatives. In binding studies, several molecules showed affinity in nanomolar and subnanomolar range at 5-HT1A and moderate to no affinity for other relevant receptors (5-HT2A, 5-HT2C, D1, D2, α1 and α2). All compounds were then evaluated in order to assess their antiproliferative

  血清素（5-羟色胺，5-HT）是参与众多生理和病理生理过程的最重要的神经介质之一。此外，众所周知，5-HT在多种类型的非肿瘤和肿瘤细胞中起生长因子的作用，最近它也与癌基因有关。在前列腺肿瘤细胞系（PC3细胞）和人类激素难治性前列腺癌组织中鉴定出5-HT 1A受体表达。基于这些观察，开发5-HT 1A拮抗剂可用于抑制癌细胞的生长。为了研究5-HT 1A的潜在用途配体作为抗增殖剂，我们分析了一组新的1-萘基哌嗪衍生物。在结合研究中，一些分子显示出纳摩尔和亚纳摩尔范围内的亲和力，在5-HT 1A和中度到其他相关的受体无亲和力（5-HT 2A，5-HT 2C，d 1，d 2，α 1和α 2） 。然后评估所有化合物，以使用PC3细胞评估其抗增殖活性，并对最具活性的化合物（1和2）进行充分表征，以确定引起所观察到的抗增殖作用的机制。