N-[2-(二甲氨基)乙基]-2-苯基喹啉-8-甲酰胺 | 107027-12-3

• 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
• 中文名称: N-[2-(二甲氨基)乙基]-2-苯基喹啉-8-甲酰胺
• 英文名称: 8-Quinolinecarboxamide, N-(2-(dimethylamino)ethyl)-2-phenyl-
• 英文别名: N-[2-(dimethylamino)ethyl]-2-phenylquinoline-8-carboxamide
• CAS: 107027-12-3
• 化学式: C₂₀H₂₁N₃O
• 分子量: 319.406
• InChiKey: DKGAQCFUFLDBDT-UHFFFAOYSA-N

物化性质

• 沸点：
  553.6±45.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-甲基-2-苯基-4-喹啉羧酸 在 盐酸 、 selenium(IV) oxide 、 铜 、 N,N'-羰基二咪唑 作用下， 反应 0.62h， 生成 N-[2-(二甲氨基)乙基]-2-苯基喹啉-8-甲酰胺
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018

文献信息

• Acridine carboxamides for the treatment of cancer
  申请人：XENOVA LIMITED

  公开号：EP0642343B1

  公开（公告）日：2000-08-30
• TREATMENT OF CANCERS
  申请人：XENOVA LIMITED

  公开号：EP0642343A1

  公开（公告）日：1995-03-15
• [EN] TREATMENT OF CANCERS<br/>[FR] TRAITEMENT DES CANCERS
  申请人：——

  公开号：WO1993024096A2

  公开（公告）日：1993-12-09

  [EN] A new treatment schedule for administration of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide and other related carboxamide anticancer drugs in which the drug is administered in a divided-dose shedule comprising two or more administrations at frequent intervals, for example every hour. Schedules to produce cyclic peaks/troughs in plasma levels are mentioned. The compounds can be used for circumventing multidrug resistance in cancers and may, for example, be used in combination with other cytotoxic drugs, especially non-topo II inhibitors. Treatment of melanoma and advanced colon cancer is included.
  [FR] L'invention se rapporte à un nouveau mode de traitement visant à administrer N-[2-(diméthylamino)éthyl)acridine-4-carboxamide et d'autres anticancéreux carboxamides apparentés. Le médicament est administré en doses fractionnées, en au moins deux fois, à intervalles fréquents, par exemple, toutes les heures. On établit des schémas pour obtenir des pics/creux cycliques dans les niveaux de plasma. Les composés peuvent être utilisés pour vaincre la résistance des cancers aux multiples médicaments, et peuvent être utilisés, par exemple, en combinaison avec d'autres médicaments cytotoxiques, notamment des inhibiteurs non-topo II. L'invention concerne également le traitement du mélanome et du cancer avancé du côlon.
• Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity
  作者：Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00122a018

  日期：1989.2

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.