2-((1-Anthracenylmethyl)amino)-2-methyl-1,3-propanediol | 96404-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-((1-Anthracenylmethyl)amino)-2-methyl-1,3-propanediol
• 英文别名: 2-(Anthracen-1-ylmethylamino)-2-methylpropane-1,3-diol
• CAS: 96404-63-6
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: KUPZBMGVLLMQLO-UHFFFAOYSA-N

物化性质

• 沸点：
  543.9±35.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-蒽甲酸 在 sodium tetrahydroborate 、 硼烷 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-((1-Anthracenylmethyl)amino)-2-methyl-1,3-propanediol
  参考文献：
  名称：

  2-[(Arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

  摘要：

  The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs with DNA increases as the intercalating ring system grows in area, with three distinct binding levels evident. Isomers from a specific ring system appear to bind DNA similarly. DNA binding is not the sole criterion for antitumor activity for the AMAPs studied; the magnitude of the DELTA-T(m) does not correlate with the antitumor activity observed. Significant in vivo P388 activity was seen for AMAP congeners from several tetracyclic ring systems. However, isomers from each of the specific ring systems produced a wide range of in vivo P388 activity. Thus, AMAP antitumor activity is not a function of the ring system per se, but rather appears to be related to the shape of the specific molecule. Three AMAP congeners (crisnatol (770U82, 773U82, and 502U83) are currently in clinical trials.

  DOI：

  10.1021/jm00111a010

文献信息

• Polycyclic aromatic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0125702B1

  公开（公告）日：1987-08-12
• BAIR, KENNETH W.
  作者：BAIR, KENNETH W.

  DOI：——

  日期：——
• US4719047A
  申请人：——

  公开号：US4719047A

  公开（公告）日：1988-01-12
• US4719049A
  申请人：——

  公开号：US4719049A

  公开（公告）日：1988-01-12
• US4803226A
  申请人：——

  公开号：US4803226A

  公开（公告）日：1989-02-07