4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid | 214637-82-8

• 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: 4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
• 英文别名: 4-methyl-11-oxoindeno[1,2-b]quinoline-6-carboxylic acid
• CAS: 214637-82-8
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: LGQZAYLAVANWRU-UHFFFAOYSA-N

物化性质

• 沸点：
  588.970±38.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.439±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 75.0h， 生成 4-methyl-N-[2-[methyl-[3-[methyl-[2-[(4-methyl-11-oxoindeno[1,2-b]quinoline-6-carbonyl)amino]ethyl]amino]propyl]amino]ethyl]-11-oxoindeno[1,2-b]quinoline-6-carboxamide
  参考文献：
  名称：

  Synthesis and antitumor activity of some indeno[1,2- b ]quinoline-based bis carboxamides

  摘要：

  A series of bis(11-oxo-1 1H-indeno[1,2-b]quinoline-6-carboxamides) linked through the B-carboxamides were prepared by coupling the requisite acid imidazolides with Various diamines. Compounds with mono-cationic linker chains were more potent cytotoxins than the corresponding monomer in a panel of rodent and human cell lines: while those with the dicationic linker chains (CH2)(2)NR(CH2)(2)NR(CH2)(2) and (CH2)(2)NR(CH2)(3)NR(CH2)(2) showed extraordinarily high potencies (for example, IC(50)s of 0.18-1.4 nM against human Jurkat leukemia; up to 1000-fold more potent than the parent monomer). As seen previously in the monomeric series, small, lipophilic 4-substituents significantly increased potency in cell culture. The dimeric compounds were all slightly to significantly more potent in the mutant JL(A) and JL(D) cell lines that under-express topo II, suggesting that this enzyme is not their primary target. An Il-imino-linked dimer was much less active, and an asymmetric indeno[1,2-b]quinoline-6-carboxamide/naphthalimide dimer was less active than the comparable symmetric bis(indeno[1,2-b]quinoline-6-carboxamide). Selected analogues were active against sub-cutaneously implanted colon 38 tumors in mice? giving growth delays comparable to that of the clinical topo I inhibitor irinotecan at up to 10-fold lower doses. These compounds form an interesting new class of putative topo I inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00039-0
• 作为产物：
  描述：

  4-methyl-11H-indeno[1,2-b]quinoline-6,10-dicarboxylic acid 在 potassium permanganate 、 sodium carbonate 作用下， 以 水 为溶剂， 55.0~300.0 ℃ 、66.66 Pa 条件下， 反应 0.25h， 生成 4-methyl-11-oxo-11H-indeno[1,2-b]quinoline-6-carboxylic acid
  参考文献：
  名称：

  Ring-substituted 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides with similar patterns of cytotoxicity to the dual topo I/II inhibitor DACA

  摘要：

  A series of ring-substituted analogues of the topoisomerase inhibitor 11-oxo-11H-indeno[1,2-b]quinoline-6-carboxamides was prepared and evaluated. The compounds were prepared by Pfitzinger reaction of the appropriate isatin-7-carboxylic acids and 1-indanones, followed by selective thermal decarboxylation of the resulting tetracyclic diacids, subsequent oxidation of the methylene group with alkaline permanganate under carefully controlled conditions, and 1,1'-carbonyldiimidazole-induced amidation. The compounds were evaluated in a panel of cell lines in culture. The largest increases in cytotoxicity (five to tenfold) were shown by 4-substituted analogues, with the 4-Cl derivative having an IC50 of 8 nM against the Lewis lung carcinoma. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00231-x