(+/-)-2-(N-tert-butylamino)-4'-aminopropiophenone | 104657-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-2-(N-tert-butylamino)-4'-aminopropiophenone
• 英文别名: 1-(4-aminophenyl)-2-tert.-butylaminopropanone；1-(4-Aminophenyl)-2-(tert-butylamino)propan-1-one
• CAS: 104657-22-9
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: QAGNMLSSMWOXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(N-tert-butylamino)-4'-aminopropiophenone 在 sodium iodide 、 氯-(4-甲基苯基)磺酰基亚胺钠 、 sodium hydroxide 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  (±)-2-(N-tert-Butylamino)-3′-[125I]-iodo-4′-azidopropiophenone: A dopamine transporter and nicotinic acetylcholine receptor photoaffinity ligand based on bupropion (Wellbutrin, Zyban)

  摘要：

  Towards addressing the knowledge gap of how bupropion interacts with the dopamine transporter (DAT) and nicotinic acetylcholine receptors (nAChRs), a ligand was synthesized in which the chlorine of bupropion was isosterically replaced with an iodine and a photoreactive azide was added to the 4'-position of the aromatic ring. Analog (+/-)-3 (SADU-3-72) demonstrated modest DAT and alpha 4 beta 2 nAChR affinity. A radioiodinated version was shown to bind covalently to hDAT expressed in cultured cells and affinity-purified, lipid-reincorporated human alpha 4 beta 2 neuronal nAChRs. Co-incubation of (+/-)-[I-125]-3 with non-radioactive (+/-)-bupropion or (-)-cocaine blocked labeling of these proteins. Compound (+/-)-[I-125]-3 represents the first successful example of a DAT and nAChR photoaffinity ligand based on the bupropion scaffold. Such ligands are expected to assist in mapping bupropion-binding pockets within plasma membrane monoamine transporters and ligand-gated nAChR ion channels. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.086
• 作为产物：
  描述：

  4-乙酰氨基丙正离子基酰苯 在 N-甲基吡咯烷酮 、 盐酸 、 水 、 溴 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 3.17h， 生成 (+/-)-2-(N-tert-butylamino)-4'-aminopropiophenone
  参考文献：
  名称：

  (±)-2-(N-tert-Butylamino)-3′-[125I]-iodo-4′-azidopropiophenone: A dopamine transporter and nicotinic acetylcholine receptor photoaffinity ligand based on bupropion (Wellbutrin, Zyban)

  摘要：

  Towards addressing the knowledge gap of how bupropion interacts with the dopamine transporter (DAT) and nicotinic acetylcholine receptors (nAChRs), a ligand was synthesized in which the chlorine of bupropion was isosterically replaced with an iodine and a photoreactive azide was added to the 4'-position of the aromatic ring. Analog (+/-)-3 (SADU-3-72) demonstrated modest DAT and alpha 4 beta 2 nAChR affinity. A radioiodinated version was shown to bind covalently to hDAT expressed in cultured cells and affinity-purified, lipid-reincorporated human alpha 4 beta 2 neuronal nAChRs. Co-incubation of (+/-)-[I-125]-3 with non-radioactive (+/-)-bupropion or (-)-cocaine blocked labeling of these proteins. Compound (+/-)-[I-125]-3 represents the first successful example of a DAT and nAChR photoaffinity ligand based on the bupropion scaffold. Such ligands are expected to assist in mapping bupropion-binding pockets within plasma membrane monoamine transporters and ligand-gated nAChR ion channels. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.086

文献信息

• Dérivés de 1-(aminophényl)-2-amino-propanone, leur utilisation en thérapeutique et leur procédé de préparation
  申请人：LABORATOIRE L. LAFON Société anonyme dite:

  公开号：EP0174242B1

  公开（公告）日：1988-01-13
• US4980377A
  申请人：——

  公开号：US4980377A

  公开（公告）日：1990-12-25
• (±)-2-(N-tert-Butylamino)-3′-[125I]-iodo-4′-azidopropiophenone: A dopamine transporter and nicotinic acetylcholine receptor photoaffinity ligand based on bupropion (Wellbutrin, Zyban)
  作者：David J. Lapinsky、Shaili Aggarwal、Tammy L. Nolan、Christopher K. Surratt、John R. Lever、Rejwi Acharya、Roxanne A. Vaughan、Akash Pandhare、Michael P. Blanton

  DOI：10.1016/j.bmcl.2011.10.086

  日期：2012.1

  Towards addressing the knowledge gap of how bupropion interacts with the dopamine transporter (DAT) and nicotinic acetylcholine receptors (nAChRs), a ligand was synthesized in which the chlorine of bupropion was isosterically replaced with an iodine and a photoreactive azide was added to the 4'-position of the aromatic ring. Analog (+/-)-3 (SADU-3-72) demonstrated modest DAT and alpha 4 beta 2 nAChR affinity. A radioiodinated version was shown to bind covalently to hDAT expressed in cultured cells and affinity-purified, lipid-reincorporated human alpha 4 beta 2 neuronal nAChRs. Co-incubation of (+/-)-[I-125]-3 with non-radioactive (+/-)-bupropion or (-)-cocaine blocked labeling of these proteins. Compound (+/-)-[I-125]-3 represents the first successful example of a DAT and nAChR photoaffinity ligand based on the bupropion scaffold. Such ligands are expected to assist in mapping bupropion-binding pockets within plasma membrane monoamine transporters and ligand-gated nAChR ion channels. (C) 2011 Elsevier Ltd. All rights reserved.