1,3,5-tri-(5-bromopent-1-ynyl)-benzene | 943552-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-tri-(5-bromopent-1-ynyl)-benzene
• 英文别名: 1,3,5-tris-(5-bromopent-1-ynyl)-benzene；1,3,5-Tris(5-bromopent-1-ynyl)benzene
• CAS: 943552-44-1
• 化学式: C₂₁H₂₁Br₃
• 分子量: 513.11
• InChiKey: ZXSIZVFYQBHGGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.3±50.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,5-tri-(5-bromopent-1-ynyl)-benzene 在 potassium iodide 作用下， 生成 1,3,5-tris(5-iodopent-1-yn-1-yl)benzene
  参考文献：
  名称：

  Novel bis-2,2,6,6-tetramethylpiperidine (bis-TMP) and bis-mecamylamine antagonists at neuronal nicotinic receptors mediating nicotine-evoked dopamine release

  摘要：

  By linking two or three mecamylamine or 2,2,6,6-tetramethylpiperidine (TMP) molecules together via a linear lipophilic bis-methylene linker or a specially designed conformationally restricted tris-linker, a series of bis- and tris-tertiary amine analogs has been synthesized and evaluated as potent antagonists at nAChRs mediating nicotine-evoked [H-3] dopamine release from rat striatal slices. Compounds 7e, 14b and 16 demonstrated high potency in decreasing nicotine-evoked [H-3] dopamine release (IC50 = 2.2, 46, and 107 nM, respectively). The preliminary structure-activity data obtained with these new analogs suggest the importance of the length of the methylene linker in the bis-analog series. Such bis-tertiary amino analogs may provide a new strategy for the design of drugable ligands that have high inhibitory potency against nAChRs mediating nicotine-evoked dopamine release in striatum, which have been suggested to be target receptors of interest in the development of potential smoking cessation therapies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.089
• 作为产物：
  描述：

  1,3,5-tris-(5-hydroxypent-1-ynyl)benzene 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 1,3,5-tri-(5-bromopent-1-ynyl)-benzene
  参考文献：
  名称：

  tris-Azaaromatic quaternary ammonium salts: Novel templates as antagonists at nicotinic receptors mediating nicotine-evoked dopamine release

  摘要：

  A series of tris-azaaromatic quaternary ammonium salts has been synthesized and evaluated for their ability to inhibit neuronal nicotinic acetylcholine receptors (nAChRs) mediating nicotine-evoked [H-3]dopamine release from superfused rat striatal slices and for inhibition of [H-3]nicotine and [H-3]methyllycaconitine binding to whole rat brain membranes. The 3-picolinium compound 1,3,5-tri-{5-[1-(3-picolinium)]-pent-1-ynyl} benzene tribromide (tPy3PiB), 3b, exhibited high potency and selectivity for nAChR subtypes mediating nicotine-evoked [H-3]dopamine release with an IC50 of 0.2 nM and I-max of 67%. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.062

文献信息

• USE OF A NOVEL ALPHA-7 nAChR ANTAGONIST TO SUPPRESS PATHOGENIC SIGNAL TRANSDUCTION IN CANCER AND AIDS
  申请人：PAPKE Roger L.

  公开号：US20100179186A1

  公开（公告）日：2010-07-15

  This application provides a method for the use of select quaternary ammonium antagonists to alpha-7 nAChR for the treatment of cancer and HIV and AIDS.

  该应用程序提供了一种使用选择性四价铵拮抗剂对α-7 nAChR进行治疗癌症、HIV和艾滋病的方法。
• TRIS-QUARTERNARY AMMONIUM SALTS AND METHODS FOR MODULATING NEURONAL NICOTINIC ACETYLCHOLINE RECEPTORS
  申请人：Crooks Peter A.

  公开号：US20110105556A1

  公开（公告）日：2011-05-05

  Provided are tris-quaternary ammonium compounds which are modulators of nicotinic acetylocholine receptors. Also provided are methods of using the compounds for modulating the function of a nicotinic acetylcholine receptor, and for the prevention and/or treatment of central nervous system disorders, substance use and/or abuse and or gastrointestinal tract disorders.

  提供了三元-四元铵化合物，它们是乙酰胆碱受体的调节剂。还提供了使用这些化合物调节乙酰胆碱受体功能、预防和/或治疗中枢神经系统疾病、物质使用和/或滥用以及胃肠道疾病的方法。
• Tris-Quaternary Ammonium Salts and Methods for Modulating Neuronal Nicotinic Acetylcholine Receptors
  申请人：University of Kentucky Research Foundation

  公开号：US20130030018A1

  公开（公告）日：2013-01-31

  Provided are tris-quaternary ammonium compounds which are modulators of nicotinic acetylocholine receptors. Also provided are methods of using the compounds for modulating the function of a nicotinic acetylcholine receptor, and for the prevention and/or treatment of central nervous system disorders, substance use and/or abuse and or gastrointestinal tract disorders.

  提供的是三元-四元铵化合物，它们是乙酰胆碱受体的调节剂。还提供了使用这些化合物调节乙酰胆碱受体功能的方法，以及用于预防和/或治疗中枢神经系统疾病、物质使用和/或滥用以及胃肠道疾病的方法。
• Use of a Novel Alpha-7 Nachr Antagonist to Suppress Pathogenic Signal Transduction in Cancer and Aids
  申请人：UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION

  公开号：US20130231366A1

  公开（公告）日：2013-09-05

  This application provides a method for the use of select quaternary ammonium antagonists to alpha-7 nAChR for the treatment of cancer and HIV and AIDS.

  这个应用程序提供了一种使用选择性四元铵拮抗剂对α-7 nAChR进行治疗癌症和HIV / AIDS的方法。
• WO2007/76112
  申请人：——

  公开号：——

  公开（公告）日：——