2-<2-Amino-aethylmercaptomethyl>-benzimidazol | 95166-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-<2-Amino-aethylmercaptomethyl>-benzimidazol
• 英文别名: 2-[(2-Aminoethyl)thiomethyl]benzimidazole；2-(1H-benzimidazol-2-ylmethylsulfanyl)ethanamine
• CAS: 95166-71-5
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: CQCHFFYXSFYIJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  445.0±30.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-Amino-aethylmercaptomethyl>-benzimidazol 生成 N-[2-(2-benzimidazolylmethylthio)ethyl]-N'-nitroguanidine
  参考文献：
  名称：

  Pharmacologically active guanidine compounds

  摘要：

  这些化合物是取代的硫代烷基、氨基烷基和氧烷基胍，它们是组胺活性的抑制剂。

  公开号：

  US03950333A1
• 作为产物：
  描述：

  2-氯甲基苯并咪唑 、 半胱胺盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以90%的产率得到2-<2-Amino-aethylmercaptomethyl>-benzimidazol
  参考文献：
  名称：

  Effect of the triphenylphosphonium cation on the biological properties of new rhenium and technetium-99m fac-[M(CO)3(NSN)]±-type complexes: Synthesis, structural characterization, in vitro and in vivo studies

  摘要：

  Triphenylphosphonium (TPP) cations have been used for the development of tumor or myocardial diagnostic radiopharmaceuticals. In this work, the development of new [Tc-99m][Tc(CO)(3)(N,S,N)](+) complexes of the (N,S,N) tridentate chelator benzimidazol-2-yl-methylthioethylamine (L), and its triphenylphosphonium (TPP) cation derivative L-TPP is described. The TPP-moiety was conjugated at the N-tau-benzimidazol position of L. The reaction of the chelators L and L-TPP with a suitable precursor [Re(sol)(3)(CO)(3)](+) yielded single products of ReL+ and ReL-TPP2+. The complexes were characterized by spectroscopic methods and furthermore the structure of ReL was elucidated by X-ray crystallography. The respective Tc-99m-radiotracers were synthesized in high yield, their lipophilicity was measured and both exhibited high stability in cysteine, histidine solutions as well as in rat plasma. The in vitro cell studies in human erythroleukemia K-562 and glioblastoma U-87MG tumor cells showed that the tracer (TcL+)-Tc-99m exhibited significantly higher cellular uptake, while (TcL)-Tc-99m-TPP2+ exhibited sig-nificantly higher mitochondrial accumulation. The tracers (TcL+)-Tc-99m and 99mTcL-TPP2+ exhibited fast blood elimination and excretion via the hepatobiliary and the renal routes after intravenous administration in healthy mice. Tracer (TcL+)-Tc-99m exhibited higher myocardial uptake and renal excretion, while (TcL)-Tc-99m-TPP2+ exhibited primarily hepatobiliary excretion. These data confirm the high mitochondrial accumulation of (TcL)-Tc-99m-TPP2+ in vitro and show its potential as a candidate for tumor imaging.

  DOI：

  10.1016/j.ica.2020.119807

文献信息

• Pharmacologically active thiourea and urea compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US03950353A1

  公开（公告）日：1976-04-13

  The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.

  这些化合物是取代的硫代烷基、氨基烷基和氧烷基硫脲和脲，它们是组胺活性的抑制剂。
• Copper(I) complexes with ligand systems containing nitrogen and sulphur donor atoms. Spectroscopy and electrochemistry of the copper(II)/copper(I) couple
  作者：Michele Gullotti、Luigi Casella、Gianfranco Pallanza、Franco Laschi、Piero Zanello

  DOI：10.1016/s0277-5387(00)86751-0

  日期：1990.1

  of copper(I) complexes with imine ligands resulting from the condensation of 3-formyl-1-phenyl-2-(1H)-pyridinethione with aminoalkylthioalkylbenzimidazoles has been synthesized and spectroscopically characterized. The redox propensity of the present copper(I) complexes, investigated by electrochemical techniques, confirms the relatively difficult access to the corresponding copper(II) complexes, as

  摘要合成了3-甲酰基-1-苯基-2-（1H）-吡啶硫酮与氨基烷基硫代烷基苯并咪唑缩合生成的一系列亚胺配体的铜（I）配合物。通过电化学技术研究，本发明的铜（I）配合物的氧化还原倾向证实了相对难于获得相应的铜（II）配合物，这是基于其先前报道的电化学方法所期望的。讨论了伴随铜（I）/铜（II）氧化还原变化的结构重组。
• Electrochemical synthesis of zinc(II), cadmium(II), and nickel(II) complexes of tetradentate Schiff-base ligands derived from aminothioether imidazoles
  作者：Rufina Bastida、Teresa Lage、Conception Parrado、Teresa Rodriguez、Antonio Sousa、David E. Fenton

  DOI：10.1039/dt9900002101

  日期：——

  The electrochemical synthesis and physicochemical properties of neutral zinc(II), cadmium(II), and nickel(II) complexes of Schiff bases derived from aminothioether imidazoles and substituted salicylaldehydes are reported.

  报道了衍生自氨基硫醚咪唑和取代的水杨醛的席夫碱的中性锌（II），镉（II）和镍（II）配合物的电化学合成和理化性质。
• Synthese positiv inotroper Substanzen: Imidazolylpropylguanidine mit Pyridin-Partialstruktur
  作者：Armin Buschauer

  DOI：10.1002/ardp.19883210709

  日期：——

  Durch zweifache Aminolyse von N‐Benzoyl‐diphenylimidocarbonat und anschließende saure Hydrolyse wurden unsymmetrisch substituierte Imidazolylpropylguanidine hergestellt. Die Substanzen wirken am H2‐Rezeptor des Atriums und am Papillarmuskel des Meerschweinchens bis zu 20mal stärker agonistisch als Histamin.

  Durch zweifache Aminolyse von N-Benzoyl-diphenylimidocarbonat und anschließende saure Hydrolyse wurden unsymmetrisch substituierte Imidazolylpropylguanidine hergestellt。Die Substanzen wirken am H2-Rezeptor des Atriums und am Papilmuskel des Meerschweinchens bis zu 20mal stärker agonistisch als Histamin。
• Pharmacologically active guanidine compounds in compositions and methods
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04154844A1

  公开（公告）日：1979-05-15

  The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.

  这些化合物是替代了硫代烷基、氨基烷基和氧基烷基的胍，它们是组胺活性的抑制剂。