1-[2-(Dimethylamino)ethyl]-7-methyl-2,3-dihydro-1,8-naphthyridin-4-one | 494748-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-[2-(Dimethylamino)ethyl]-7-methyl-2,3-dihydro-1,8-naphthyridin-4-one
• CAS: 494748-70-8
• 化学式: C₁₃H₁₉N₃O
• 分子量: 233.313
• InChiKey: WDOGCTPEUXDVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(Dimethylamino)ethyl]-7-methyl-2,3-dihydro-1,8-naphthyridin-4-one 在 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 [2-(8-Methoxy-3-methyl-indolo[3,2-c][1,8]naphthyridin-5-yl)-ethyl]-dimethyl-amine
  参考文献：
  名称：

  Dialkylaminoalkylindolonaphthyridines as potential antitumour agents: synthesis, cytotoxicity and DNA binding properties

  摘要：

  The synthesis of new planar derivatives characterised by the presence of an indolonaphthyridine nucleus, carrying a dimethylaminoethyl or a dimethylaminopropyl side chain is reported. The antiproliferative activity of the new products was tested by means of an in vitro assay on human tumour cell lines (HL-60 and HeLa). A number of compounds (1a-d, 1h) showed IC50 values comparable to that obtained with the well-known drug ellipticine on the HL-60 cell line. The interaction with DNA was also investigated. Linear flow dichroism measurements allowed us to understand the interaction geometry. The thermodynamic parameters of the binding process, i.e. intrinsic binding constant and exclusion parameter, were determined by fluorimetric titration. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01372-7
• 作为产物：
  描述：

  7-甲基-1,8-萘啶-4(1h)-酮 在 氢氧化钾 、 sodium tetrahydroborate 、 环己酮 、 aluminum isopropoxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 99.0h， 生成 1-[2-(Dimethylamino)ethyl]-7-methyl-2,3-dihydro-1,8-naphthyridin-4-one
  参考文献：
  名称：

  Dialkylaminoalkylindolonaphthyridines as potential antitumour agents: synthesis, cytotoxicity and DNA binding properties

  摘要：

  The synthesis of new planar derivatives characterised by the presence of an indolonaphthyridine nucleus, carrying a dimethylaminoethyl or a dimethylaminopropyl side chain is reported. The antiproliferative activity of the new products was tested by means of an in vitro assay on human tumour cell lines (HL-60 and HeLa). A number of compounds (1a-d, 1h) showed IC50 values comparable to that obtained with the well-known drug ellipticine on the HL-60 cell line. The interaction with DNA was also investigated. Linear flow dichroism measurements allowed us to understand the interaction geometry. The thermodynamic parameters of the binding process, i.e. intrinsic binding constant and exclusion parameter, were determined by fluorimetric titration. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01372-7

文献信息

• Dialkylaminoalkylindolonaphthyridines as potential antitumour agents: synthesis, cytotoxicity and DNA binding properties
  作者：Lisa Dalla Via、Ornella Gia、Sebastiano Marciani Magno、Antonio Da Settimo、Giampaolo Primofiore、Federico Da Settimo、Francesca Simorini、Anna Maria Marini

  DOI：10.1016/s0223-5234(02)01372-7

  日期：2002.6

  The synthesis of new planar derivatives characterised by the presence of an indolonaphthyridine nucleus, carrying a dimethylaminoethyl or a dimethylaminopropyl side chain is reported. The antiproliferative activity of the new products was tested by means of an in vitro assay on human tumour cell lines (HL-60 and HeLa). A number of compounds (1a-d, 1h) showed IC50 values comparable to that obtained with the well-known drug ellipticine on the HL-60 cell line. The interaction with DNA was also investigated. Linear flow dichroism measurements allowed us to understand the interaction geometry. The thermodynamic parameters of the binding process, i.e. intrinsic binding constant and exclusion parameter, were determined by fluorimetric titration. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.