9-(2-chloroacetamido)-1-azabenzanthrone | 946433-65-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 9-(2-chloroacetamido)-1-azabenzanthrone
• CAS: 946433-65-4
• 化学式: C₁₈H₁₁ClN₂O₂
• 分子量: 322.751
• InChiKey: DWEOMUKLTSLWJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-(2-chloroacetamido)-1-azabenzanthrone 在 sodium iodide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 27.0h， 生成
  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-nitro-1-azabenzanthrone 在 sodium sulfide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 9-(2-chloroacetamido)-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

• Hybrids of oxoisoaporphine-tacrine congeners: Novel acetylcholinesterase and acetylcholinesterase-induced β-amyloid aggregation inhibitors
  作者：Huang Tang、Li-Zhen Zhao、Hao-Tao Zhao、Shi-Liang Huang、Shu-Ming Zhong、Jiang-Ke Qin、Zhen-Feng Chen、Zhi-Shu Huang、Hong Liang

  DOI：10.1016/j.ejmech.2011.08.002

  日期：2011.10

  inhibit AChE, butyrylcholinesterase (BChE), AChE-induced and self-induced β-amyloid (Aβ) aggregation. The new hybrids consist of a unit of 1-azabenzanthrone and a tacrine or its congener, connected through an oligomethylene linker containing an amine group at variable position. These hybrids exhibit high AChE inhibitory activity with IC50 values in the nanomolar range in most cases. Moreover, five out

  一系列的双结合位点乙酰胆碱酯酶抑制剂已被设计，合成和其抑制乙酰胆碱酯酶，丁酰胆碱酯酶（BChE的）的能力进行测试，乙酰胆碱酯酶诱导的和自感应β淀粉样蛋白（β）集合。新的杂种由1-氮杂苯并蒽酮和他克林或其同类物组成，它们通过在可变位置上含有胺基的低聚亚甲基接头连接。在大多数情况下，这些杂种表现出高的AChE抑制活性，IC 50值在纳摩尔范围内。此外，五出这一系列的12个杂交体，特别是那些带有四氢部分，显示出在朝向乙酰胆碱酯酶诱导的和自感应的体外抑制活性的显著β 聚集，使其成为有希望的抗阿尔茨海默氏症候选药物。
• 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.