(chloro-3 propyl)-3-3H-benzotriazine-1,2,3 one-4 | 91532-04-6

• 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: (chloro-3 propyl)-3-3H-benzotriazine-1,2,3 one-4
• 英文别名: 3-(3-chloropropyl)-1,2,3-benzotriazin-4(3H)-one；3-(3-chloropropyl)-1,2,3-benzotriazin-4(3H)one；3-(3-chloropropyl)-1,2,3-benzotriazin-4-one
• CAS: 91532-04-6
• 化学式: C₁₀H₁₀ClN₃O
• 分子量: 223.662
• InChiKey: LEYBAKHCSDIBMH-UHFFFAOYSA-N

物化性质

• 沸点：
  358.7±44.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：

  1-苄基哌嗪 、 (chloro-3 propyl)-3-3H-benzotriazine-1,2,3 one-4 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84%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：

  2-氨基-N-(3-羟丙基)苯甲酰胺 在 盐酸 、 sodium nitrite 作用下， 生成 (chloro-3 propyl)-3-3H-benzotriazine-1,2,3 one-4
  参考文献：
  名称：

  Synthèse et activité anti-dépressive potentielle de nouvelles triazine-1,2,3 ones-4

  摘要：

  DOI：

  10.1016/0223-5234(87)90272-8

文献信息

• Substituted-3-indolyl-4-piperidino-alkyl heterocycles for the treatment of depression
  申请人：Wyeth

  公开号：US20040204402A1

  公开（公告）日：2004-10-14

  A compound represented by the formula I: 1 wherein A represents the following heterocycles: 2 and R 1-9 are as defined herein, a composition containing this compound and methods for treating disorders of the serotonin-affected neurological systems utilizing such a compound or composition.

  一个由化学式I:1表示的化合物，其中A代表以下的杂环：2，而R1-9如本文所定义，包含该化合物的组合物以及利用该化合物或组合物治疗受到5-羟色胺影响的神经系统紊乱的方法。
• 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。
• 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：——
• US6939870B2
  申请人：——

  公开号：US6939870B2

  公开（公告）日：2005-09-06