18-Methoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16(21),17,19-heptaene | 162106-65-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 18-Methoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16(21),17,19-heptaene
• CAS: 162106-65-2
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: JRCMRDWXSAWDJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  18-Methoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16(21),17,19-heptaene 在 palladium on activated charcoal 异丙苯 作用下， 反应 18.0h， 以16%的产率得到3-methoxybenzindolo<3,2-h>quinolizine
  参考文献：
  名称：

  Indoles XIII. Syntheses and Stereochemistry of 14H-Bisindolo[2,3-a][3,2-h]quinolizine and of Some Benz[a]indolo[3,2-h]quinolizines

  摘要：

  Starting from hexahydrobenz[a]indolo[3,2-h]quinolizine (1a-c) and hexahydrobisindolo[2,3-a][3,2-h]quinolizine (4)(2) we succeeded in generating their completely dehydrogenated derivatives. The structures were investigated by H-1- and C-13-nmr spectroscopy as well as by X-ray analysis.

  DOI：

  10.3987/com-94-6915
• 作为产物：
  描述：

  在 三氯氧磷 、 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 24.0h， 以42%的产率得到18-Methoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-2(10),4,6,8,16(21),17,19-heptaene
  参考文献：
  名称：

  Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists

  摘要：

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.093

文献信息

• Lehmann Jochen, Nieger Martin, Witt Thomas, Heterocycles, 41 (1995) N 1, S 119-130
  作者：Lehmann Jochen, Nieger Martin, Witt Thomas

  DOI：——

  日期：——