2-(2(RS)-aminopropyl)-5-bromothiophene | 137945-29-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2(RS)-aminopropyl)-5-bromothiophene
• 英文别名: 1-(5-bromo-2-thienyl)-2-aminopropane；1-(5-Bromothiophen-2-yl)propan-2-amine
• CAS: 137945-29-0
• 化学式: C₇H₁₀BrNS
• 分子量: 220.133
• InChiKey: IUSCMKANJIRNRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2(RS)-aminopropyl)-5-bromothiophene 、 丙酮 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以98%的产率得到N-isopropyl-2-(2(RS)-aminopropyl)-5-bromothiophene
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5-iodothiophenes as brain imaging agents

  摘要：

  Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)-5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene by radioiodination of the corresponding 5-boronic acid or 5-(trimethylstannyl) derivatives. Tissue distribution studies in rats with 2-(2(RS)-aminopropyl)-5-[I-126]iodothiophene showed high brain uptake (5 min. 2.77% dose/g 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).

  DOI：

  10.1021/jm00080a012
• 作为产物：
  描述：

  (E)-2-bromo-5-(2-nitropropenyl)thiophene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-(2(RS)-aminopropyl)-5-bromothiophene
  参考文献：
  名称：

  Heteroarylisopropylamines as MAO inhibitors

  摘要：

  The in vitro monoamine oxidase inhibitory (MAOI) activities of 11 heteroarylisopropylamines vis-a-vis MAO-A and MAO-B were described and interpreted in terms of possible interactions with the enzyme active site. Molecular dynamics simulations allowed a comparison between the most active MAO-A inhibitor of the series, the 1-(2-benzofuryl)-2-aminopropane, and the specific, analogous MAO-A substrate serotonin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.045

文献信息

• US4900539A
  申请人：——

  公开号：US4900539A

  公开（公告）日：1990-02-13
• US4914215A
  申请人：——

  公开号：US4914215A

  公开（公告）日：1990-04-03
• Heteroarylisopropylamines as MAO inhibitors
  作者：Gabriel Vallejos、Angélica Fierro、Marcos Caroli Rezende、Silvia Sepúlveda-Boza、Miguel Reyes-Parada

  DOI：10.1016/j.bmc.2005.04.045

  日期：2005.7

  The in vitro monoamine oxidase inhibitory (MAOI) activities of 11 heteroarylisopropylamines vis-a-vis MAO-A and MAO-B were described and interpreted in terms of possible interactions with the enzyme active site. Molecular dynamics simulations allowed a comparison between the most active MAO-A inhibitor of the series, the 1-(2-benzofuryl)-2-aminopropane, and the specific, analogous MAO-A substrate serotonin. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5-iodothiophenes as brain imaging agents
  作者：Mark M. Goodman、George W. Kabalka、Ronald C. Marks、F. F. Knapp、J. Lee、Y. Liang

  DOI：10.1021/jm00080a012

  日期：1992.1

  Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)-5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)-aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5-iodothiophene by radioiodination of the corresponding 5-boronic acid or 5-(trimethylstannyl) derivatives. Tissue distribution studies in rats with 2-(2(RS)-aminopropyl)-5-[I-126]iodothiophene showed high brain uptake (5 min. 2.77% dose/g 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).