decahydro-5-quinolinol | 92187-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: decahydro-5-quinolinol
• 英文别名: 1,2,3,4,4a,5,6,7,8,8a-decahydroquinolin-5-ol
• CAS: 92187-37-6
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: ACFFUQQAWWRDRR-UHFFFAOYSA-N

物化性质

• 沸点：
  265.9±13.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  decahydro-5-quinolinol 在 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 pyridinium dichromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 116.0h， 生成 (+/-)-trans-4,5,5a,6,7,8,9,9a-octahydrothiazolo<4,5-f>quinolin-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
• 作为产物：
  描述：

  2,3,4,6,7,8-hexahydro-5(1H)-quinolinone 在 PtO₂ 作用下， 以 溶剂黄146 为溶剂， 以24.80 g (36.2%)的产率得到decahydro-5-quinolinol
  参考文献：
  名称：

  Hetero [f] fused carbocyclic pyridines as dopaminergic agents

  摘要：

  描述了异构[f]融合的碳环吡啶，以及制备和制备相同的药物组合物的方法，这些药物组合物可作为选择性作用于突触前多巴胺受体的多巴胺激动剂，并可用作多巴胺能、抗精神病和降压剂，以及用于治疗与高催乳素血症相关的疾病和中枢神经系统疾病。

  公开号：

  US04762843A1

文献信息

• Thiazolo [f]-fused hexahydroquinoline derivatives as dopaminergic agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0260642A2

  公开（公告）日：1988-03-23

  Hetero [f] fused carbocyclic pyridines of the formula I are described, as well as processes for the preparation and pharmaceutical compositions of same, which are useful as dopamine agonists with selectivity for the presynaptic dopamine receptor and are useful as dopaminergic, antipsychotic and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.

  描述了式 I 的杂[f]融合碳环吡啶及其制备工艺和药物组合物。 描述了其作为多巴胺激动剂对突触前多巴胺受体具有选择性的作用，可用作多巴胺能药、抗精神病药和抗高血压药以及治疗高泌乳素血症相关疾病和中枢神经系统疾病。
• CAPRATHE, BRADLEY W.;JAEN, JUAN C.;WISE, LAWRENCE D.
  作者：CAPRATHE, BRADLEY W.、JAEN, JUAN C.、WISE, LAWRENCE D.

  DOI：——

  日期：——
• US4762843A
  申请人：——

  公开号：US4762843A

  公开（公告）日：1988-08-09