9-[4-(Dimethylamino)butyramido]-1-azabenzanthrone | 946433-80-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 异卟啉
• 英文名称: 9-[4-(Dimethylamino)butyramido]-1-azabenzanthrone
• 英文别名: 4-(dimethylamino)-N-(8-oxo-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-5-yl)butanamide
• CAS: 946433-80-3
• 化学式: C₂₂H₂₁N₃O₂
• 分子量: 359.428
• InChiKey: IQHJJVHUYGOXCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[4-(Dimethylamino)butyramido]-1-azabenzanthrone 、 碘甲烷 以 氯仿 为溶剂， 反应 24.0h， 以67%的产率得到Trimethyl-[4-oxo-4-[(8-oxo-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-5-yl)amino]butyl]azanium;iodide
  参考文献：
  名称：

  Derivatives of oxoisoaporphine alkaloids: A novel class of selective acetylcholinesterase inhibitors

  摘要：

  A series of 9-aminoalkanamido-1-azabenzanthrones derviatives (3a-i Ar-NHCO(CH2)(n)(NRR2)-R-1) and their quaternary methiodide salts (4a-g Ar-NHCO(CH2)(n)N+(CH3)(RRI-)-R-1-I-2) were designed and synthesized as acetyleholinesterase (AChE) or butyr-ylcholinesterase (BuChE) inhibitors. The synthetic compounds exhibited high AChE inhibitory activity with IC50 values in the nanomolar range and high selectivity for AChE over BuChE (45- to 1980-fold). The structure-activity relationships (SARs) were discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.015
• 作为产物：
  描述：

  9-aminooxoisoaporphine 在 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 98.5h， 生成 9-[4-(Dimethylamino)butyramido]-1-azabenzanthrone
  参考文献：
  名称：

  Derivatives of oxoisoaporphine alkaloids: A novel class of selective acetylcholinesterase inhibitors

  摘要：

  A series of 9-aminoalkanamido-1-azabenzanthrones derviatives (3a-i Ar-NHCO(CH2)(n)(NRR2)-R-1) and their quaternary methiodide salts (4a-g Ar-NHCO(CH2)(n)N+(CH3)(RRI-)-R-1-I-2) were designed and synthesized as acetyleholinesterase (AChE) or butyr-ylcholinesterase (BuChE) inhibitors. The synthetic compounds exhibited high AChE inhibitory activity with IC50 values in the nanomolar range and high selectivity for AChE over BuChE (45- to 1980-fold). The structure-activity relationships (SARs) were discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.015

文献信息

• Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity
  作者：Huang Tang、Xiao-Dong Wang、Yong-Biao Wei、Shi-Liang Huang、Zhi-Shu Huang、Jia-Heng Tan、Lin-Kun An、Jian-Yong Wu、Albert Sun-Chi Chan、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2007.07.004

  日期：2008.5

  A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH2)(n)NR2, Ar = 1-azabenzanthrone, n = 1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (it = 2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity. (C) 2007 Elsevier Masson SAS. All rights reserved.