9-Methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline | 340966-75-8

• 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: 9-Methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline
• CAS: 340966-75-8
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: RGBKZQPQBJSBKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline 在 copper(I) oxide 、 甲酸 、 mercury(II) diacetate 、 碘 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 8.75h， 生成 (+/-)-cis-9-methoxy-1-methyl-6-(methylthio)-1,2,3,4,4a,5,10,10a-octahydrobenzoquinoline
  参考文献：
  名称：

  Centrally acting .alpha.1-adrenoceptor agonists based on hexahydronaphth[2,3-b]-1,4-oxazines and octahydrobenzo[g]quinolines

  摘要：

  Centrally acting alpha(1)-agonists may be of therapeutic value in dementias and other CNS disorders characterized by symptoms of noradrenergic insufficiency. Therefore, on the basis of known peripherally acting alpha(1)-agonists two new groups of centrally acting alpha(1)-agonists with improved lipophilicity, the hexahydronaphth[2,3-b]-1,4-oxazines type A and the octahydrobenzo[g]quinolines type B were designed. The N-methylated derivatives 14 and 33 demonstrate potent, direct agonistic activity at postjunctional alpha(1)-receptors. Ring substituent alterations in compounds of type A and B change the potency of compounds on the rabbit ear artery by over 3 orders of magnitude (pD2 = 5.35-8.40). The efficacy of these compounds varies from 42 to 110%. These alpha(1)-agonists which were selective in the pithed rat increase vigilance in rats. Compound 14 was found to be a centrally acting alpha(1)-agonist with good tolerability in different animal species and in healthy volunteers. Furthermore, 14 selectively stimulates the breakdown of phosphatidylinositol in rat cerebral cortex slices. In vivo, the compound reverses behavioral deficits in animals which received noradrenergic lesions following DDC or DSP4 treatment. Oxazine 14 and its close derivatives are by far more lipophilic than commonly known alpha(1)-agonists. This is demonstrated in a ClogP-PROBIS plot.

  DOI：

  10.1021/jm00081a008
• 作为产物：
  描述：

  (+/-)-3-(2-cyanoethyl)-8-methoxy-2-tetralone 以 乙醇 、 氯仿 为溶剂， 反应 30.0h， 生成 9-Methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline
  参考文献：
  名称：

  Centrally acting .alpha.1-adrenoceptor agonists based on hexahydronaphth[2,3-b]-1,4-oxazines and octahydrobenzo[g]quinolines

  摘要：

  Centrally acting alpha(1)-agonists may be of therapeutic value in dementias and other CNS disorders characterized by symptoms of noradrenergic insufficiency. Therefore, on the basis of known peripherally acting alpha(1)-agonists two new groups of centrally acting alpha(1)-agonists with improved lipophilicity, the hexahydronaphth[2,3-b]-1,4-oxazines type A and the octahydrobenzo[g]quinolines type B were designed. The N-methylated derivatives 14 and 33 demonstrate potent, direct agonistic activity at postjunctional alpha(1)-receptors. Ring substituent alterations in compounds of type A and B change the potency of compounds on the rabbit ear artery by over 3 orders of magnitude (pD2 = 5.35-8.40). The efficacy of these compounds varies from 42 to 110%. These alpha(1)-agonists which were selective in the pithed rat increase vigilance in rats. Compound 14 was found to be a centrally acting alpha(1)-agonist with good tolerability in different animal species and in healthy volunteers. Furthermore, 14 selectively stimulates the breakdown of phosphatidylinositol in rat cerebral cortex slices. In vivo, the compound reverses behavioral deficits in animals which received noradrenergic lesions following DDC or DSP4 treatment. Oxazine 14 and its close derivatives are by far more lipophilic than commonly known alpha(1)-agonists. This is demonstrated in a ClogP-PROBIS plot.

  DOI：

  10.1021/jm00081a008

文献信息

• Stereoselective synthesis of methoxy substituted 1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolines
  作者：Charlotta Mellin、Uli Hacksell

  DOI：10.1016/s0040-4020(01)87725-5

  日期：1987.1

  The preparation of the cis- and trans-isomers of 6- and 9-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]-quinoline is reported. The syntheses involved reductions of cyclic iminium chlorides, which afforded the diastereomers conveniently and in good yields. Small cis/trans ratios were obtained with NaCNBH3 as the reducing agent. Catalytic hydrogenation using PtO2 in THF or t-BuOH gave the largest cis/trans

  报道了6-和9-甲氧基-1,2,3,4,4a，5,10,10a-八氢苯并[g]-喹啉的顺式和反式异构体的制备。合成涉及环状亚氯化亚胺的还原，这方便地且以高收率提供了非对映异构体。用NaCNBH 3作为还原剂可获得小的顺式/反式比率。使用PtO 2在THF或t-BuOH中的催化加氢得到最大的顺式/反式比。制备N-苄基衍生物以允许确定相对立体化学。
• [EN] SILYLATED HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSES HETEROCYCLIQUES SILYLES
  申请人：NOVARTIS AG

  公开号：WO2001036428A1

  公开（公告）日：2001-05-25

  The invention provides a compound of formula (I), wherein X and R1 to R5 are as defined in the description, and the preparation thereof. The compounds of formula (I) are useful as pharmaceuticals.
• Centrally acting .alpha.1-adrenoceptor agonists based on hexahydronaphth[2,3-b]-1,4-oxazines and octahydrobenzo[g]quinolines
  作者：Joachim Nozulak、Jean M. Vigouret、Anne L. Jaton、Alfred Hofmann、Anant R. Dravid、Hans P. Weber、Hans O. Kalkman、Malcolm D. Walkinshaw

  DOI：10.1021/jm00081a008

  日期：1992.2

  Centrally acting alpha(1)-agonists may be of therapeutic value in dementias and other CNS disorders characterized by symptoms of noradrenergic insufficiency. Therefore, on the basis of known peripherally acting alpha(1)-agonists two new groups of centrally acting alpha(1)-agonists with improved lipophilicity, the hexahydronaphth[2,3-b]-1,4-oxazines type A and the octahydrobenzo[g]quinolines type B were designed. The N-methylated derivatives 14 and 33 demonstrate potent, direct agonistic activity at postjunctional alpha(1)-receptors. Ring substituent alterations in compounds of type A and B change the potency of compounds on the rabbit ear artery by over 3 orders of magnitude (pD2 = 5.35-8.40). The efficacy of these compounds varies from 42 to 110%. These alpha(1)-agonists which were selective in the pithed rat increase vigilance in rats. Compound 14 was found to be a centrally acting alpha(1)-agonist with good tolerability in different animal species and in healthy volunteers. Furthermore, 14 selectively stimulates the breakdown of phosphatidylinositol in rat cerebral cortex slices. In vivo, the compound reverses behavioral deficits in animals which received noradrenergic lesions following DDC or DSP4 treatment. Oxazine 14 and its close derivatives are by far more lipophilic than commonly known alpha(1)-agonists. This is demonstrated in a ClogP-PROBIS plot.