6-chloro-3-piperazinylbenzisoxazole | 87757-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-chloro-3-piperazinylbenzisoxazole
• 英文别名: 3-(1-piperazinyl)-6-chloro-1,2-benzisoxazole；6-chloro-3-piperazin-1-yl-benzisoxazole；6-chloro-3-piperazin-1-yl-1,2-benzoxazole
• CAS: 87757-07-1
• 化学式: C₁₁H₁₂ClN₃O
• 分子量: 237.689
• InChiKey: LLNLKVNLPROIDY-UHFFFAOYSA-N

物化性质

• 沸点：
  418.8±35.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  6-chloro-3-piperazinylbenzisoxazole 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.0h， 生成 3-(4-((1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)methyl)piperazin-1-yl)-6-chlorobenzo[d]isoxazole
  参考文献：
  名称：

  寻求有效的抗结核药：各种（（三唑/吲哚）-哌嗪-1-基/ 1,4-二氮杂-1-基）苯并[ d ]异恶唑衍生物的设计，合成，抗结核活性和对接研究

  摘要：

  一系列三十八个新颖的3-（4-（（取代的-1 H -1,2,3-三唑-4-基）甲基）哌嗪-1-基/ 1,4-二氮杂-1-基）苯并[ d ]异恶唑和1-（4-（苯并[ d ]异恶唑-3-基）哌嗪-1-基/ 1,4-二氮杂-1-基）-2-（1 H-吲哚-3-基）取代合成-1-一种类似物，使用多种分析技术进行表征，并评估其对结核分枝杆菌H37Rv菌株和两种“野生”菌株Spec的体外抗结核活性。210和规格 192。标题化合物的最小抑菌浓度（MIC）为6.16至> 200μM。在测试的化合物中，7i，7y和7z表现出中等活性（MIC = 24.03–29.19μM），7j表现出非常好的抗结核活性（MIC = 6.16μM ）。此外，在筛选毒性时，发现7i，7j，7y和7z对小鼠巨噬细胞系无毒。将所有合成的化合物对接至泛酸合成酶位点，以了解与受体的不同结合相互作用。

  DOI：

  10.1016/j.bmcl.2016.03.059
• 作为产物：
  描述：

  4-氯-N,2-二羟基苯胺 在 氯化亚砜 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 24.5h， 生成 6-chloro-3-piperazinylbenzisoxazole
  参考文献：
  名称：

  EP2322520

  摘要：

  公开号：

文献信息

• Benzisothiazole and benzisoxazole piperazine derivatives
  申请人：Mead Johnson & Company

  公开号：US04411901A1

  公开（公告）日：1983-10-25

  Disubstituted N,N-piperazinyl derivatives are disclosed wherein one substituent is benzisothiazol-3-yl or benzisoxazol-3-yl and the other is alkylene attached to heterocycles such as azaspiro[4.5]decanedione, dialkylglutarimide, thiazolidinedione and spirocyclopentylthiazolidinedione or butyrophenone-like groups. The compounds have psychotropic properties and 8-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspior[4.5]deca ne-7,9-dione is a typical embodiment having selective antipsychotic activity.

  本发明公开了二取代的N，N-哌嗪衍生物，其中一个取代基是苯并异噻唑-3-基或苯并异恶唑-3-基，另一个取代基是连接到杂环上的烷基，例如氮杂螺[4.5]癸二酮，二烷基谷氨酰胺，噻唑烷二酮和螺环戊基噻唑烷二酮或丁酰苯酮类似的基团。这些化合物具有精神药理学性质，8-[4-[4-(1,2-苯并异噻唑-3-基)-1-哌嗪基]丁基]-8-氮杂螺[4.5]癸-7,9-二酮是一种具有选择性抗精神病活性的典型实施例。
• Aralkyl Substituted Piperidine or Piperazine Derivatives and Their Use for Treating Schizophrenia
  申请人：Li Jianqi

  公开号：US20110160199A1

  公开（公告）日：2011-06-30

  The present invention discloses an aralkyl substituted piperidine or piperazine derivative and the use of the derivative in preparation of medicaments for treating schizophrenia and correlative psychoneuroses. It is shown by pharmacological tests that the derivative of the present invention has better antischizophrenic effect and less toxicity. Said derivative is a free base or salt of the compound having the following general formula.

  本发明揭示了一种芳基烷基取代的哌啶或哌嗪衍生物，以及该衍生物在制备治疗精神分裂症和相关精神神经症的药物中的应用。药理学测试表明，本发明的衍生物具有更好的抗精神分裂症效果和较小的毒性。所述衍生物是以下一般式化合物的自由碱基或盐。
• Aralkyl substituted piperidine or piperazine derivatives and their use for treating schizophrenia
  申请人：Li Jianqi

  公开号：US08653069B2

  公开（公告）日：2014-02-18

  The present invention discloses an aralkyl substituted piperidine or piperazine derivative and the use of the derivative in preparation of medicaments for treating schizophrenia and correlative psychoneuroses. It is shown by pharmacological tests that the derivative of the present invention has better antischizophrenic effect and less toxicity. Said derivative is a free base or salt of the compound having the following general formula.

  本发明公开了一种芳基烷基取代的哌啶或哌嗪衍生物及其在制备治疗精神分裂症和相关精神神经症的药物中的应用。药理学测试表明，本发明的衍生物具有更好的抗精神分裂症作用和更少的毒性。所述衍生物是具有以下通式的化合物的自由碱基或盐。
• ARALKYL SUBSTITUTED PIPERIDINE OR PIPERAZINE DERIVATIVES AND THEIR USE FOR TREATING SCHIZOPHRENIA
  申请人：Jiangsu Guohua Investment Co., Ltd

  公开号：EP2322520A1

  公开（公告）日：2011-05-18

  The present invention discloses an aralkyl substituted piperidine or piperazine derivative and the use of the derivative in preparation of medicaments for treating schizophrenia and correlative psychoneuroses. It is shown by pharmacological tests that the derivative of the present invention has better antischizophrenic effect and less toxicity. Said derivative is a free base or salt of the compound having the following general formula.

  本发明公开了一种芳基取代的哌啶或哌嗪衍生物，以及该衍生物在制备治疗精神分裂症和相关精神神经症的药物中的用途。药理试验表明，本发明的衍生物具有较好的抗精神分裂症作用，毒性较小。所述衍生物是具有以下通式的化合物的游离碱或盐。
• Synthesis and biological evaluation of 1-(1,2-benzisothiazol-3-yl)- and (1,2-benzisoxazol-3-yl)piperazine derivatives as potential antipsychotic agents
  作者：Joseph P. Yevich、James S. New、David W. Smith、Walter G. Lobeck、John D. Catt、Joseph L. Minielli、Michael S. Eison、Duncan P. Taylor、Leslie A. Riblet、Davis L. Temple

  DOI：10.1021/jm00153a010

  日期：1986.3

  Members of the series of title compounds were tested for potential antipsychotic activity in relevant receptor binding assays and behavioral screens. Structure-activity relationships within the series are discussed. Compound 24 (BMY 13859-1), a (1,2-benzisothiazol-3-yl)piperazine derivative, was selected for further study because of its potent and selective profile in primary CNS tests. It was active in the Sidman avoidance paradigm and blocked amphetamine-induced stereotyped behavior in dogs for up to 7 h. The compound's lack of typical neuroleptic-like effects in the rat catalepsy test and its failure to produce dopamine receptor supersensitivity following chronic administration indicate that it should not cause the movement disorders commonly associated with antipsychotic therapy. Although 24 has potent affinity for dopaminergic binding sites, its even greater affinity for serotonin receptors suggests that a serotonergic component may be relevant to its atypical profile. Compound 24 is currently undergoing clinical evaluation in schizophrenic patients.