(Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane | 1231952-05-8

• 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: (Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane
• 英文别名: tert-butyl-dimethyl-[(Z)-1-(3-nitrophenyl)prop-1-enoxy]silane
• CAS: 1231952-05-8
• 化学式: C₁₅H₂₃NO₃Si
• 分子量: 293.438
• InChiKey: JWJMDENELJPMSC-AUWJEWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以75%的产率得到(R)-1-(3-nitrophenyl)-2-hydroxypropan-1-one
  参考文献：
  名称：

  Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation

  摘要：

  To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropion's possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,35)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3',4'-dichlorophenyl [(+/-)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3'-fluorophenyl, 3'-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of alpha 4 beta 2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,35)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of alpha 4 beta 2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.

  DOI：

  10.1021/jm1003232
• 作为产物：
  描述：

  3-硝基苯丙酮 、 叔丁基二甲硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane
  参考文献：
  名称：

  Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation

  摘要：

  To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropion's possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,35)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3',4'-dichlorophenyl [(+/-)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3'-fluorophenyl, 3'-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of alpha 4 beta 2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,35)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of alpha 4 beta 2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.

  DOI：

  10.1021/jm1003232
• 作为试剂：
  描述：

  tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane 、 3-nitro-1-phenyl-propan-1-one 、 叔丁基二甲硅基三氟甲磺酸酯 、 三乙胺 在 (Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane 、 alumina 作用下， 以 二氯甲烷 为溶剂， 以8.0 g (98%) of 9g was isolated as colorless oil的产率得到(Z)-tert-butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane
  参考文献：
  名称：

  HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

  摘要：

  本发明提供了羟基丁酮类似物，能够抑制一个或多个单胺的再摄取，并/或作为尼古丁乙酰胆碱受体的拮抗剂。这些化合物可以选择性地结合到一个或多个单胺转运体，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体，和/或可以选择性地结合到一个或多个尼古丁乙酰胆碱受体亚型。这些化合物可用于治疗对单胺水平调节和/或尼古丁乙酰胆碱受体拮抗有反应的疾病，包括药物依赖、抑郁症和肥胖症。

  公开号：

  US20150141416A1

文献信息

• Hydroxybupropion analogues for treating drug dependence
  申请人：Research Triangle Institute

  公开号：US08906908B2

  公开（公告）日：2014-12-09

  The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

  该发明提供了羟基丁酮类似物，能够抑制一个或多个单胺的再摄取，并/或作为尼古丁乙酰胆碱受体的拮抗剂。这些化合物可以选择性地结合到一个或多个单胺转运体，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体，和/或可以选择性地结合到一个或多个尼古丁乙酰胆碱受体亚型。这些化合物可以用于治疗对单胺水平修饰和/或尼古丁乙酰胆碱受体拮抗剂有反应的疾病，包括药物依赖、抑郁症和肥胖症。
• Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation
  作者：Ronald J. Lukas、Ana Z. Muresan、M. Imad Damaj、Bruce E. Blough、Xiaodong Huang、Hernán A. Navarro、S. Wayne Mascarella、J. Brek Eaton、Syndia K. Marxer-Miller、F. Ivy Carroll

  DOI：10.1021/jm1003232

  日期：2010.6.24

  To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropion's possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,35)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3',4'-dichlorophenyl [(+/-)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3'-fluorophenyl, 3'-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of alpha 4 beta 2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,35)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of alpha 4 beta 2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.
• HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE
  申请人：Research Triangle Institute

  公开号：US20130150357A1

  公开（公告）日：2013-06-13

  The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

  本发明提供了一种羟基丙酮类似物，能够抑制一个或多个单胺的再吸收和/或作为尼古丁乙酰胆碱受体的拮抗剂。这些化合物可以选择性地结合到一个或多个单胺转运体上，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体，和/或可以选择性地结合到一个或多个尼古丁乙酰胆碱受体亚型上。这些化合物可以用于治疗对单胺水平调节和/或尼古丁乙酰胆碱受体拮抗剂敏感的疾病，包括药物依赖、抑郁症和肥胖症。