[cyclopropyl(isothiocyanate)methyl]cyclopropane | 1247603-60-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: [cyclopropyl(isothiocyanate)methyl]cyclopropane
• 英文别名: [Cyclopropyl(isothiocyanato)methyl]cyclopropane
• CAS: 1247603-60-6
• 化学式: C₈H₁₁NS
• mdl: MFCD14676314
• 分子量: 153.248
• InChiKey: IYBYGPRXCBJXDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [cyclopropyl(isothiocyanate)methyl]cyclopropane 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 N-(dicyclopropylmethyl)-4,5-dihydro-1,3-thiazol-2-amine
  参考文献：
  名称：

  New 2-Aminothiazoline derivatives lower blood pressure of spontaneously hypertensive rats (SHR) via I1-imidazoline and alpha-2 adrenergic receptors activation

  摘要：

  2-Aminothiazolines share an isosteric relationship with imidazolines and oxazolines with antihypertensive activity mainly mediated by the imidazoline I-1-receptor. In the present work, we have prepared five aminothiazolines, following a previously described synthetic pathway. Aminothiazolines derived from dicyclo-propylmethylamine (ATZ1) and cyclohexylamine (3) are unprecedented in the literature. Competitive radioligand assay was carried out with all synthetic compounds, and the I-1 receptor affinity in comparison to rilmenidine in PC12 cells was determined. Surprisingly, the rilmenidine isoster (ATZ1) showed no I-1-receptor interaction. Diethyl (ATZ4) and 2-ethyl-hexylamine (ATZ5) derivatives bind to the receptor with 11.98 and 10.94 nmol/l, respectively. These compounds were selected for in vivo experiments. Both compounds reduced the blood pressure of spontaneously hypertensive rats (SHR). The hypotensive effect of these compounds was abrogated in the presence of a(2) adrenergic (yohimbine) and I-1 (efaroxan) receptor antagonists suggesting that both aminothiazolines bind to the adrenergic and imidazoline receptors. Lipinski's descriptors of the synthesized aminothiazolines were calculated and are similar to the known imidazoline I-1 receptor ligands. 3D-Similarity between ATZ5 and agmatine, the natural imidazoline receptor ligand, was also observed.

  DOI：

  10.1016/j.ejphar.2016.10.009
• 作为产物：
  描述：

  二硫化碳 、 双环丙基甲胺 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 [cyclopropyl(isothiocyanate)methyl]cyclopropane
  参考文献：
  名称：

  New 2-Aminothiazoline derivatives lower blood pressure of spontaneously hypertensive rats (SHR) via I1-imidazoline and alpha-2 adrenergic receptors activation

  摘要：

  2-Aminothiazolines share an isosteric relationship with imidazolines and oxazolines with antihypertensive activity mainly mediated by the imidazoline I-1-receptor. In the present work, we have prepared five aminothiazolines, following a previously described synthetic pathway. Aminothiazolines derived from dicyclo-propylmethylamine (ATZ1) and cyclohexylamine (3) are unprecedented in the literature. Competitive radioligand assay was carried out with all synthetic compounds, and the I-1 receptor affinity in comparison to rilmenidine in PC12 cells was determined. Surprisingly, the rilmenidine isoster (ATZ1) showed no I-1-receptor interaction. Diethyl (ATZ4) and 2-ethyl-hexylamine (ATZ5) derivatives bind to the receptor with 11.98 and 10.94 nmol/l, respectively. These compounds were selected for in vivo experiments. Both compounds reduced the blood pressure of spontaneously hypertensive rats (SHR). The hypotensive effect of these compounds was abrogated in the presence of a(2) adrenergic (yohimbine) and I-1 (efaroxan) receptor antagonists suggesting that both aminothiazolines bind to the adrenergic and imidazoline receptors. Lipinski's descriptors of the synthesized aminothiazolines were calculated and are similar to the known imidazoline I-1 receptor ligands. 3D-Similarity between ATZ5 and agmatine, the natural imidazoline receptor ligand, was also observed.

  DOI：

  10.1016/j.ejphar.2016.10.009

文献信息

• Triazole pyridyl compounds as agonists of the APJ receptor
  申请人：AMGEN INC.

  公开号：US10689367B2

  公开（公告）日：2020-06-23

  Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the structures where the definitions of the variables are provided herein.

  式 I 和式 II 的化合物、其药学上可接受的盐、前述任何化合物的立体异构体或其混合物是 APJ 受体的激动剂，可用于治疗心血管疾病和其他疾病。式 I 和式 II 的化合物具有本文提供的变量定义的结构。
• TRIAZOLE PYRIDYL COMPOUNDS AS AGONISTS OF THE APJ RECEPTOR
  申请人：AMGEN INC.

  公开号：US20190300507A1

  公开（公告）日：2019-10-03

  Compounds of Formula I and Formula II, pharmaceutically acceptable salt thereof, stereoisomers of any of the foregoing, I or mixtures thereof are agonists of the APJ Receptor and may have use in treating cardiovascular and other conditions. Compounds of Formula I and Formula II have the structures where the definitions of the variables are provided herein.