4-(5-bromopentyl)-1,1'-biphenyl | 136617-77-1

• 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: 4-(5-bromopentyl)-1,1'-biphenyl
• 英文别名: 1-(5-bromopentyl)-4-phenylbenzene
• CAS: 136617-77-1
• 化学式: C₁₇H₁₉Br
• 分子量: 303.242
• InChiKey: RERMWDJRJKNINO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4-(5-bromopentyl)-1,1'-biphenyl 在 potassium dihydrogenphosphate 、 sodium methylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.17h， 生成 Methyl 3-cyano-3-hydroxy-4-[5-(4-phenylphenyl)pentylsulfanyl]butanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  对苯基苯甲醛 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 二异丁基氢化铝 、 dimsyl sodium 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 2.42h， 生成 4-(5-bromopentyl)-1,1'-biphenyl
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w

文献信息

• Zwitterionic Sulfobetaine Inhibitors of Squalene Synthase
  作者：Thomas A. Spencer、Thomas J. Onofrey、Reginald O. Cann、Jonathon S. Russel、Laura E. Lee、Daniel E. Blanchard、Alfredo Castro、Peide Gu、Guojian Jiang、Ishaiahu Shechter

  DOI：10.1021/jo981617q

  日期：1999.2.1

  A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in

  已经合成了大量的磺基甜菜碱（例如10种），并根据其两性离子结构具有有助于在活性位点结合和通过细胞膜通过的特性，被认为是鲨烯合酶（SS）的抑制剂。 。当将简单的磺基甜菜碱部分掺入含有疏水部分的化合物中时，如法呢基二磷酸酯（1）或角鲨烯二磷酸酯（2）中的那些，确实在大鼠肝微粒体测定中观察到了SS的抑制作用。例如，法呢基化磺基甜菜碱10具有抑制SS的IC（50）＝10μM，而芳香族衍生物35具有IC（50）＝2μM。研究了多种结构修饰，例如化合物43、52、76、85、91、99、111和115。不幸，
• Mono Quaternary Ammonium Salts and Methods for Modulating Neuronal Nicotinic Acetylcholine Receptors
  申请人：Crooks Peter

  公开号：US20100113511A1

  公开（公告）日：2010-05-06

  Provided are monoquaternary ammonium compounds which are modulators of nicotinic acetylcholine 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.

  提供了单季铵化合物，它们是尼古丁乙酰胆碱受体的调节剂。还提供了使用这些化合物调节尼古丁乙酰胆碱受体功能，以及预防和/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。
• Mono quaternary ammonium salts and methods for modulating neuronal nicotinic acetylcholine receptors
  申请人：Crooks Peter

  公开号：US08846937B2

  公开（公告）日：2014-09-30

  Provided are monoquaternary ammonium compounds which are modulators of nicotinic acetylcholine 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.

  提供了单季铵化合物，它们是尼古丁乙酰胆碱受体的调节剂。还提供了使用这些化合物调节尼古丁乙酰胆碱受体功能、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。
• WO2007/149392
  申请人：——

  公开号：——

  公开（公告）日：——
• Sulfobetaine zwitterionic inhibitors of squalene synthase
  作者：Ishaiahu Shechter、Peide Gu、Guojian Jiang、Thomas J. Onofrey、Reginald O. Cann、Alfredo Castro、Thomas A. Spencer

  DOI：10.1016/0960-894x(96)00485-4

  日期：1996.11

  Zwitterions such as farnesyl sulfobetaine 8 are a new type of inhibitor of squalene synthase that, while maintaining overall neutrality, mimic both the carbocationic and anionic moieties of presumed reaction intermediates. The most effective zwitterionic sulfobetaines discovered to date are aromatic derivatives 17 (IC50 = 2 mu M) and 20 (IC50 = 5 mu M). Copyright (C) 1996 Elsevier Science Ltd