14β-aminocodeinone | 68615-94-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 14β-aminocodeinone
• 英文别名: (4R,4aS,7aR,12bR)-4a-amino-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 68615-94-1
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: UJRPISFPVNXKJY-XFKAJCMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  14β-aminocodeinone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以84%的产率得到14β-amino-7,8-dihydrocodeinone
  参考文献：
  名称：

  14个β-（2-溴乙酰氨基）吗啡和14个β-（2-溴乙酰氨基）吗啡酮。

  摘要：

  优选从蒂巴因和1-氯-1-亚硝基环己烷的加合物制备14-β-（2-溴乙酰氨基）吗啡（6）和14-β-（2-溴乙酰氨基）吗啡酮（9），将其在甲醇溶液中还原后得到14。 -氨基可待因酮（2）和相应的缩酮（3）。在受体结合试验中测试时，IC50值6和9分别为15和10 nM。如果将测定期间的孵育时间从15分钟增加到30分钟，则观察到两种配体的不可逆结合。

  DOI：

  10.1021/jm00366a024
• 作为产物：
  描述：

  14β-nitrocodeinone dimethyl acetal 在 盐酸 、 ammonium chloride 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 14β-aminocodeinone
  参考文献：
  名称：

  用四硝基甲烷硝化蒂巴因

  摘要：

  蒂巴因（1）在甲醇中与四硝基甲烷反应，得到14β-硝基可待因酮二甲基乙缩醛（2a）作为主要产物，该产物已特别转化为14β-硝基可待因酮（3a），14β-氨基可待因酮二甲基乙缩醛（2b） ，14β-氨基可待因酮（3b）和14β-氨基可待因。在氧气存在下在苯中用四硝基甲烷硝化蒂巴因的过程不同。主要产物已被鉴定为通过一系列降解生成新的10α-羟基-和10-氧代-蒂巴因衍生物的环状过氧化物8α，10α-环氧双氧-8,14-二氢-14β-硝基蒂巴因（5）。

  DOI：

  10.1039/p19810001143

文献信息

• Formation of aziridinones (α-lactams) from hydroxamic derivatives
  作者：Christine M. Bladon、Gordon W. Kirby

  DOI：10.1039/c39820001402

  日期：——

  Various NO-disubstituted derivatives of chloroaceto- and phenylaceto-hydroxamic acid are shown to cyclise with base to give aziridinones with cleavage of the N–O bond, a process exemplified by an efficient synthesis of 1-t-buty-3-phenylaziridin-2-one.

  氯乙酰乙酸和苯基乙酰氧肟酸的各种NO-二取代衍生物已显示与碱环化，生成带有N-O键断裂的叠氮基吡啶酮，该过程以1-t-buty-3-phenylaziridin-2的有效合成为例。 -一。
• Kirby, Gordon W.; McLean, David, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1443 - 1446
  作者：Kirby, Gordon W.、McLean, David

  DOI：——

  日期：——
• 14.beta.-[(p-Nitrocinnamoyl)amino]morphinones, 14.beta.-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinones, and their codeinone analogs: synthesis and receptor activity
  作者：Alice Sebastian、Jean M. Bidlack、Qi Jiang、Darlene Deecher、Milton Teitler、Stanley D. Glick、Sydney Archer

  DOI：10.1021/jm00073a015

  日期：1993.10

  A series of 14beta-[(nitrocinnamoyl)amino]codeinones and morphinones, some of which contain a 5beta-Methyl group, were prepared from 14beta-aminocodeinones and 14beta-[N-(cyclopropylmethyl)-amino]norcodeinones. The affinities of the target compounds for the mu, delta, and kappa opioid receptors were determined by radiolabeled binding experiments using bovine brain membranes. An analogous series of 7,8-dihydrocodeinones and morphinones was prepared and assayed in the same systems. The 3-methoxy derivatives 3 and 4 were more selective than the corresponding morphinones for the mu receptor. The 5beta-methylcodeinones 25 and 27 had lower affinity at all receptors than the corresponding morphinones, but the 5beta-methylmorphinones had affinities similar to the morphinones 5 and 6. A similar pattern was observed in the 7,8-dihydro series. Two compounds, 5beta-methyl-14beta-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinone, 20 (MET-CAMO), and N-(cyclopropylmethyl)-14beta-[(p-nitrocinnamoyl)amino]-7,8-dihydronormorphinone, 22 (N-CPM-MET-CAMO), acted as nonequilibrium ligands in antinociception and membrane binding studies. In mice after icv administration, neither ligand showed any agonist activity but 8-24 h after administration both compounds acted as potent mu antagonists. A Scatchard plot of the effect of N-CPM-MET-CAMO on [H-3]DAMGO ([H-3]D-Ala2, (Me)-Phe4, Gly(ol)5]enkephalin) binding to bovine striatal membranes showed that there was a significant decrease in the B(max) value and a marginal effect on the K(d) value suggesting that the number of binding sites was reduced. When taken together, these results support the view that 20 and 22 bind covalently to the mu receptor. On the other hand, when N-acetylcysteine and 22 were allowed to react in a buffered solution, 22 was recovered unchanged. Under these conditions no Michael reaction was observed.