N-(dicyclopropylmethyl)-4,5-dihydro-1,3-thiazol-2-amine | 54187-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: N-(dicyclopropylmethyl)-4,5-dihydro-1,3-thiazol-2-amine
• 英文别名: dicyclopropylmethyl-(4,5-dihydro-thiazol-2-yl)-amine；2-(dicyclopropylmethylamino) thiazoline
• CAS: 54187-06-3
• 化学式: C₁₀H₁₆N₂S
• 分子量: 196.316
• InChiKey: WOBIGCARBWNNED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  双环丙基甲胺 在 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 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

文献信息

• Cyclopropylamines as pharmaceuticals
  申请人：Science Union et Cie, Societe Francaise de Recherche Medical

  公开号：US03988464A1

  公开（公告）日：1976-10-26

  The present invention relates to cyclopropylmethyl amines substituted by a heterocyclic radical. More particularly the heterocyclic radical is a nitrogen containing ring with 5, 6 or 7 links interrupted by another hetero atom selected from the group consisting of oxygen, sulphur and imino--NH-- The invention also relates to the acid addition salts thereof with physiologically compatible mineral or organic acids. The invention extends to the processes for making them and the intermediates produced hereto. The invention also includes the pharmaceutical compositions incorporating as active ingredient at least one compound of the invention with an inert carrier. The compounds have therapeutic utility namely on the cardio-vascular diseases and on the neuro-psychological disturbances.

  本发明涉及由杂环基取代的环丙基甲基胺。更具体地说，所述杂环基是一种含氮环，其由另一种来自氧、硫和亚胺-NH-的杂原子中断的5、6或7个链组成。该发明还涉及其与生理兼容的矿物酸或有机酸的酸盐。该发明还涉及制备它们的过程以及由此产生的中间体。该发明还包括将至少一种该发明化合物作为活性成分与惰性载体结合的药物组合物。这些化合物在心血管疾病和神经心理紊乱方面具有治疗效用。
• 2-Amino oxazolines and process for making the same
  申请人：Science-Union et Cie, Societe Francaise de Recherche Medicale

  公开号：US04102890A1

  公开（公告）日：1978-07-25

  Cyclopropylmethylamines which are substituted on the 2-position of nitrogen heterocycles so as to provide new compounds of the formula ##STR1## wherein A is oxygen, sulfur, or nitrogen; the other "R" variables in general are hydrogen, lower-alkyl, cyclopropyl, or lower-alkyl substituted cyclopropyl; and the n's are the numbers 0 to 3, inclusive, and acid addition salts thereof, are disclosed. The compounds are cardiovascular agents, which are depressive of the central nervous system. Their effects include hypnosis, analgesia, and neuro-modulation. They can be used as anti-hypertensive agents.

  本发明涉及置换在氮杂环上2位的环丙基甲基胺，以提供新的化合物，其化学式为##STR1## 其中A为氧、硫或氮; 一般情况下，其他“R”变量为氢、低烷基、环丙基或低烷基取代的环丙基; n为0至3的数字，包括其酸加成盐。这些化合物是心血管药物，能够抑制中枢神经系统。它们的效果包括催眠、镇痛和神经调节。它们可以用作降压药物。
• New 2-Aminothiazoline derivatives lower blood pressure of spontaneously hypertensive rats (SHR) via I1-imidazoline and alpha-2 adrenergic receptors activation
  作者：Renan B. Ferreira、Mariana G. de Oliveira、Edson Antunes、Wanda P. Almeida、Badr M. Ibrahim、Abdel A. Abdel-Rahman

  DOI：10.1016/j.ejphar.2016.10.009

  日期：2016.11

  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.