2-Amino-7-propyl-4,5-dihydro-thiazolo[4,5-f]isoquinolin-7-ium; iodide | 135311-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-Amino-7-propyl-4,5-dihydro-thiazolo[4,5-f]isoquinolin-7-ium; iodide
• CAS: 135311-93-2
• 化学式: C₁₃H₁₆N₃S*I
• 分子量: 373.261
• InChiKey: QJKWJHBQQIHMAQ-UHFFFAOYSA-M

反应信息

• 作为反应物：
  描述：

  2-Amino-7-propyl-4,5-dihydro-thiazolo[4,5-f]isoquinolin-7-ium; iodide 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以1.16 g的产率得到(+/-)-4,5,5a,6,7,8-hexahydro-7-propylthiazolo<4,5-f>isoquinolin-2-amine
  参考文献：
  名称：

  Dopamine autoreceptor agonists as potential antipsychotics. 3. 6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine

  摘要：

  A series of rigid tricyclic analogues of the dopamine (DA) agonist PD 118440 [4-(1,2,5,6-tetrahydro-1-propyl-3-pyridinyl)-2-thiazolamine] was synthesized and evaluated for dopaminergic activity and DA autoreceptor selectivity. (R)-(+)-6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine ((+)-6) was identified as the most selective DA autoreceptor agonist from this group of compounds. It inhibited spontaneous locomotor activity (LMA) in rodents, reversed the gamma-butyrolactone (GBL) induced accumulation of rat striatal DOPA and inhibited brain DA neuronal firing, all suggestive of direct DA autoreceptor agonist activity. However, (+)-6 is not completely free of postsynaptic DA activity, as evidenced by its stimulation of LMA in rats at high doses and its ability to produce stereotypy. On the other hand, (-)-6 appears to be a weak partial DA agonist with some effects on brain DA synthesis only at high doses. Like other DA autoreceptor agonists and DA antagonists, (+)-6 inhibited Sidman conditioned avoidance in squirrel monkeys, a test predictive of clinical antipsychotic activity. However, unlike classical antipsychotics, (+)-6 did not induce dystonias in haloperidol-sensitized squirrel monkeys, suggesting a minimal propensity toward extrapyramidal side effects (EPS).

  DOI：

  10.1021/jm00113a010