Cybl 8E | 180252-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Cybl 8E
• 英文别名: (2S)-1-(9H-carbazol-4-yloxy)-3-[[(E)-4-iodo-2-methylbut-3-en-2-yl]amino]propan-2-ol
• CAS: 180252-43-1
• 化学式: C₂₀H₂₃IN₂O₂
• 分子量: 450.319
• InChiKey: QIMLZCVAUNUVMI-VNDWYCCKSA-N

物化性质

• 沸点：
  603.6±55.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基咔唑 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 61.0h， 生成 Cybl 8E
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Characteristics of an Iodinated Analogue of the β-Adrenoceptor Antagonist Carazolol

  摘要：

  A new (radio)iodinated, beta-adrenoceptor ligand, (S)-(-)-4-[3-[(1,1-dimethyl-3-iodo-(2E)-propenyl)-amino]-2-hydroxypropoxy]carbazole (CYBL8E, 1), was prepared. 1 is an iodinated analogue of the high-affinity beta-adrenoceptor antagonist carazolol (2). The asymmetric synthesis was achieved in four steps starting from 4-hydroxycarbazole. The iodine-123-labeled form was obtained by an iododestannylation reaction with [I-123]NaI in the presence of H2O2. Using classical in vitro displacement experiments with membrane fractions of cardiac left ventricular muscle, 1 proved to have a high affinity for the receptor (K-i = 0.31 +/- 0.03). Biodistribution studies performed in New Zealand white rabbits demonstrated the specificity of the binding in vivo to the receptor. Uptake of [I-123]1 was reduced significantly in both atrial muscle, left ventricular muscle, frontal cortex, cerebellum, and striatum, by the pretreatment of the animals with different beta-adrenoceptor antagonists. In conclusion, 1 is a potent nonselective beta-adrenoceptor antagonist, which binds specifically to the beta-adrenoceptor in vivo, and is therefore a promising radioligand for the imaging of beta-adrenoceptors using single photon emission computerized tomography.

  DOI：

  10.1021/jm960122v

文献信息

• Synthesis and <i>in Vitro</i> and <i>in Vivo</i> Characteristics of an Iodinated Analogue of the β-Adrenoceptor Antagonist Carazolol
  作者：Eric A. Dubois、Jan C. van den Bos、Tamme Doornbos、Peter A. P. M. van Doremalen、G. Aernout Somsen、Jozef A. J. M. Vekemans、Anton G. M. Janssen、Harry D. Batink、Gerard J. Boer、Martin Pfaffendorf、Eric A. van Royen、Pieter A. van Zwieten

  DOI：10.1021/jm960122v

  日期：1996.1.1

  A new (radio)iodinated, beta-adrenoceptor ligand, (S)-(-)-4-[3-[(1,1-dimethyl-3-iodo-(2E)-propenyl)-amino]-2-hydroxypropoxy]carbazole (CYBL8E, 1), was prepared. 1 is an iodinated analogue of the high-affinity beta-adrenoceptor antagonist carazolol (2). The asymmetric synthesis was achieved in four steps starting from 4-hydroxycarbazole. The iodine-123-labeled form was obtained by an iododestannylation reaction with [I-123]NaI in the presence of H2O2. Using classical in vitro displacement experiments with membrane fractions of cardiac left ventricular muscle, 1 proved to have a high affinity for the receptor (K-i = 0.31 +/- 0.03). Biodistribution studies performed in New Zealand white rabbits demonstrated the specificity of the binding in vivo to the receptor. Uptake of [I-123]1 was reduced significantly in both atrial muscle, left ventricular muscle, frontal cortex, cerebellum, and striatum, by the pretreatment of the animals with different beta-adrenoceptor antagonists. In conclusion, 1 is a potent nonselective beta-adrenoceptor antagonist, which binds specifically to the beta-adrenoceptor in vivo, and is therefore a promising radioligand for the imaging of beta-adrenoceptors using single photon emission computerized tomography.