2-(N-tert-butylamino)-3'-iodo-4'-azidopropiophenone | 1354635-87-2

• 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)-3'-iodo-4'-azidopropiophenone
• 英文别名: [125I]-SADU-3-72；1-(4-Azido-3-iodophenyl)-2-(tert-butylamino)propan-1-one
• CAS: 1354635-87-2
• 化学式: C₁₃H₁₇IN₄O
• 分子量: 372.209
• InChiKey: WQMIQGVRKVRFTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N-tert-butylamino)-3'-iodo-4'-azidopropiophenone 在 盐酸 作用下， 以 乙醚 为溶剂， 以79 mg的产率得到(+/-)-2-(N-tert-butylamino)-3'-iodo-4'-azidopropiophenone hydrochloride
  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-胺基丙苯酮 在 N-甲基吡咯烷酮 、 溴 、 一氯化碘 、 三氟乙酸 、 calcium carbonate 、 sodium nitrite 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 21.92h， 生成 2-(N-tert-butylamino)-3'-iodo-4'-azidopropiophenone
  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

• (±)-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.