[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]carbamic acid isopropenyl ester | 1228307-39-8

• 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-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]carbamic acid isopropenyl ester
• 英文别名: prop-1-en-2-yl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
• CAS: 1228307-39-8
• 化学式: C₁₆H₂₂BNO₄
• 分子量: 303.166
• InChiKey: SIGIUEUKZSCOIL-UHFFFAOYSA-N

物化性质

• 沸点：
  392.6±34.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-哌啶-1-丁基-1-胺 、 [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]carbamic acid isopropenyl ester 在 1-甲基吡咯烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以5.38 g的产率得到1-(4-piperidin-1-ylbutyl)-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea
  参考文献：
  名称：

  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)

  摘要：

  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.

  DOI：

  10.1021/jm901692q
• 作为产物：
  描述：

  异丙烯基氯甲酸酯 、 4-氨基苯硼酸频哪醇酯 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 生成 [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]carbamic acid isopropenyl ester
  参考文献：
  名称：

  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)

  摘要：

  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.

  DOI：

  10.1021/jm901692q

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.