11-[2'-(dimethylamino)vinyl]benzo[b]acridine-5,12-dione | 263359-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 11-[2'-(dimethylamino)vinyl]benzo[b]acridine-5,12-dione
• 英文别名: 12-[(E)-2-(dimethylamino)vinyl]benzo[b]acridine-6,11-dione；12-[(E)-2-(dimethylamino)ethenyl]benzo[b]acridine-6,11-dione
• CAS: 263359-18-8
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: UYOCJURIBHUERU-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-[2'-(dimethylamino)vinyl]benzo[b]acridine-5,12-dione 在 水 作用下， 以9%的产率得到2-(6,11-Dioxobenzo[b]acridin-12-yl)acetaldehyde
  参考文献：
  名称：

  Identification of heteroarylenamines as a new class of antituberculosis lead molecules

  摘要：

  Enamine-containing analogues of heteroarylquinones were prepared based on initial screening data observed against Mycobacterium tuberculosis H(37)Rv (Mtb). Several analogues showed moderate to good inhibitory activity, with one analogue (7) also demonstrating acceptable toxic selectivity (MIC 0.39 mu g/mL, SI 15). Activity towards a range of single-drug-resistant strains of Mtb was suggestive of a novel mechanism of action for 7. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.010
• 作为产物：
  描述：

  11-methylbenzo[b]acridine-5,12-dione 、 N,N-二甲基甲酰胺二乙基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以94%的产率得到11-[2'-(dimethylamino)vinyl]benzo[b]acridine-5,12-dione
  参考文献：
  名称：

  细胞毒性海洋生物碱的结构研究：新的Ascididemin Ring-E类似物的合成及其体内外生物学评价

  摘要：

  为了确定母体生物碱的药学用途和结构活性要求，已经合成了具有细胞毒性的海洋生物碱阿西地敏和各种吡啶环-E类似物。在广泛的生物学筛选中评估了所有合成的化合物的选择性细胞毒性，抗病毒，抗真菌和抗微生物特性。许多类似物在体外对人实体瘤细胞系表现出选择性的细胞毒性，其中一种在体内异种移植测定中也表现出中等的抗肿瘤活性。

  DOI：

  10.1016/s0040-4020(99)01038-8

文献信息

• Identification of heteroarylenamines as a new class of antituberculosis lead molecules
  作者：Brent R. Copp、Holly C. Christiansen、Brent S. Lindsay、Scott G. Franzblau

  DOI：10.1016/j.bmcl.2005.06.010

  日期：2005.9

  Enamine-containing analogues of heteroarylquinones were prepared based on initial screening data observed against Mycobacterium tuberculosis H(37)Rv (Mtb). Several analogues showed moderate to good inhibitory activity, with one analogue (7) also demonstrating acceptable toxic selectivity (MIC 0.39 mu g/mL, SI 15). Activity towards a range of single-drug-resistant strains of Mtb was suggestive of a novel mechanism of action for 7. (c) 2005 Elsevier Ltd. All rights reserved.
• Structural Studies of Cytotoxic Marine Alkaloids: Synthesis of Novel Ring-E Analogues of Ascididemin and their in vitro and in vivo Biological Evaluation
  作者：Brent S. Lindsay、Holly C. Christiansen、Brent R. Copp

  DOI：10.1016/s0040-4020(99)01038-8

  日期：2000.1

  ascididemin and various pyridine ring-E analogues have been synthesised in an attempt to determine the pharmaceutical utility and structure-activity requirements for the parent alkaloid. All compounds synthesised were evaluated in a wide range of biological screens for selective cytotoxicity, antiviral, antifungal and antimicrobial properties. Many analogues exhibited selective cytotoxicity to human

  为了确定母体生物碱的药学用途和结构活性要求，已经合成了具有细胞毒性的海洋生物碱阿西地敏和各种吡啶环-E类似物。在广泛的生物学筛选中评估了所有合成的化合物的选择性细胞毒性，抗病毒，抗真菌和抗微生物特性。许多类似物在体外对人实体瘤细胞系表现出选择性的细胞毒性，其中一种在体内异种移植测定中也表现出中等的抗肿瘤活性。