6-(cyclopropylmethyl)-1,2-dimethoxy-4-phenyl-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 6-(cyclopropylmethyl)-1,2-dimethoxy-4-phenyl-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline
• 英文别名: 13-(Cyclopropylmethyl)-18,19-dimethoxy-15-phenyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene；13-(cyclopropylmethyl)-18,19-dimethoxy-15-phenyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
• 化学式: C₂₉H₂₉NO₄
• 分子量: 455.554
• InChiKey: OOEBRLFRLPWAPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-苄氧基-3-甲氧基-beta-硝基苯乙烯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 五氯化磷 、 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 、 tin(ll) chloride 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 142.67h， 生成 6-(cyclopropylmethyl)-1,2-dimethoxy-4-phenyl-5,6,6a,7-tetrahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]benzo[de]quinoline
  参考文献：
  名称：

  C4 phenyl aporphines with selective h5-HT2B receptor affinity

  摘要：

  A group of aporphine alkaloids related to (+/-)-nantenine (1) and bearing a C4 phenyl and various C1 or N-substituents, was synthesized and evaluated for affinity to h5-HT receptors. In general, unlike nantenine, the analogs lack affinity for the h5-HT2A receptor and other 5-HT receptors but bind selectively to the h5-HT2B receptor. With regards to 5-HT2B affinity, there appears to be a low tolerance for bulky C1 or N-substituents when the C4 phenyl moiety is present. Compound 5a had the highest 5-HT2B affinity of the compounds tested, was found to be an antagonist and is selective vs other CNS receptors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.012

文献信息

• C4 phenyl aporphines with selective h5-HT2B receptor affinity
  作者：Nirav Kapadia、Wayne W. Harding

  DOI：10.1016/j.bmcl.2015.07.012

  日期：2015.9

  A group of aporphine alkaloids related to (+/-)-nantenine (1) and bearing a C4 phenyl and various C1 or N-substituents, was synthesized and evaluated for affinity to h5-HT receptors. In general, unlike nantenine, the analogs lack affinity for the h5-HT2A receptor and other 5-HT receptors but bind selectively to the h5-HT2B receptor. With regards to 5-HT2B affinity, there appears to be a low tolerance for bulky C1 or N-substituents when the C4 phenyl moiety is present. Compound 5a had the highest 5-HT2B affinity of the compounds tested, was found to be an antagonist and is selective vs other CNS receptors. (C) 2015 Elsevier Ltd. All rights reserved.