6-bromo-N-(4-bromophenyl)hexanamide | 1232431-94-5

• 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: 6-bromo-N-(4-bromophenyl)hexanamide
• CAS: 1232431-94-5
• 化学式: C₁₂H₁₅Br₂NO
• 分子量: 349.065
• InChiKey: VERJPAGDMKNAHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吗啉 、 6-bromo-N-(4-bromophenyl)hexanamide 在 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以64%的产率得到N-(4-bromophenyl)-6-morpholinohexanamide
  参考文献：
  名称：

  Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333

  摘要：

  A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the alpha 7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a K-i range of more than an order of magnitude (K-i = 0.50 to >10 mu M), and only SEN12333 itself exhibited functional activity at the alpha 7 nAChR. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.052
• 作为产物：
  描述：

  6-溴己酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 6-bromo-N-(4-bromophenyl)hexanamide
  参考文献：
  名称：

  Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333

  摘要：

  A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the alpha 7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a K-i range of more than an order of magnitude (K-i = 0.50 to >10 mu M), and only SEN12333 itself exhibited functional activity at the alpha 7 nAChR. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.052

文献信息

• Novel Alpha-7 Nicotinic Acetylcholine Receptor Agonists Containing a Urea Moiety: Identification and Characterization of the Potent, Selective, and Orally Efficacious Agonist 1-[6-(4-Fluorophenyl)pyridin-3-yl]-3-(4-piperidin-1-ylbutyl) Urea (SEN34625/WYE-103914)
  作者：Chiara Ghiron、Simon N. Haydar、Suzan Aschmies、Hendrick Bothmann、Cristiana Castaldo、Giuseppe Cocconcelli、Thomas A. Comery、Li Di、John Dunlop、Tim Lock、Angela Kramer、Dianne Kowal、Flora Jow、Steve Grauer、Boyd Harrison、Salvatore La Rosa、Laura Maccari、Karen L. Marquis、Iolanda Micco、Arianna Nencini、Joanna Quinn、Albert J. Robichaud、Renza Roncarati、Carla Scali、Georg C. Terstappen、Elisa Turlizzi、Michela Valacchi、Maurizio Varrone、Riccardo Zanaletti、Ugo Zanelli

  DOI：10.1021/jm901692q

  日期：2010.6.10

  Alpha-7 nicotinic acetylcholine receptor (alpha 7 nAChR) agonists are promising therapeutic candidates for the treatment of cognitive impairment. We report a series of novel, potent small molecule agonists (4-18) of the alpha 7 nACh R deriving from our continuing efforts in the areas of Alzheimer's disease and schizophrenia. One of the compounds of the series containing a urea moiety (16) was further shown to be a selective agonist of the alpha 7 nAChR with excellent in vitro and in vivo profiles, brain penetration, and oral bioavailability and demonstrated in vivo efficacy in multiple behavioral cognition models. Structural modifications leading to the improved selectivity profile and the biological evaluation of this series of compounds are discussed.
• DRUG DELIVERY SYSTEM FOR TREATING DISEASE
  申请人：OSTEOANALGESIA, LLC

  公开号：US20200306380A1

  公开（公告）日：2020-10-01

  The present invention relates to HPMA-CBz copolymers and methods for treating certain diseases comprising administering the copolymers to a subject in need thereof.