2,3-bis(4-methoxyphenyl)quinoline-4-carboxylic acid | 5784-97-4

• 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: 2,3-bis(4-methoxyphenyl)quinoline-4-carboxylic acid
• 英文别名: 2,3-Bis-(4-methoxy-phenyl)-chinolin-4-carbonsaeure；2,3-Bis(4-methoxyphenyl)-4-quinolinecarboxylic acid
• CAS: 5784-97-4
• 化学式: C₂₄H₁₉NO₄
• 分子量: 385.419
• InChiKey: SMHDARQQMQFNPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-methoxyphenyl)quinoline-4-carboxylic acid 在 三氯氧磷 、 aluminum (III) chloride 作用下， 以 氯苯 为溶剂， 反应 27.0h， 以57%的产率得到9-methoxy-6-(4-methoxyphenyl)-11H-indeno[1,2-c]quinolin-11-one
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 6-arylindeno[1,2-c]quinoline derivatives

  摘要：

  A number of 6-arylindeno[1,2-c]quinoline derivatives were synthesized and evaluated for their antiproliferative activities against the growth of five cancer cell lines including human hepatocelluar carcinoma (Hep G2, Hep 3B and Hep2.2.1), non-small cell lung cancer (A549 and H1299), and normal diploid embryonic lung cell line (MRC-5). The preliminary results indicated that 9-(3-(dimethylamino) propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-2-fluoro-11H-indeno[1,2-c]quinolin-11-one (14c) was the most potent with GI(50) values of 0.61, 0.67, 0.59, and 0.72 mu M against the growth of Hep G2, Hep 3B, Hep 2.2.1, and H1299 cells, respectively. Results have also shown that 2,9-bis(3-(dimethylamino)propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-11H-indeno[1,2-c]quinolin-11-one (17), which exhibited GI(50) of 0.60 and 0.68 mu M against the growth of Hep G2 and A549, respectively, was more active than the positive topotecan and irinotecan. Compound 17 was less toxic than topotecan against the growth of normal cell (MRC-5) and therefore, was selected for further evaluation. Results indicated that compound 17 induce cell cycle arrest in G2/M phase, DNA fragmentation, and disrupt the microtubule network in A549 cells. The apoptotic induction may through the cleavage of PARP. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.021
• 作为产物：
  描述：

  脱氧茴香偶姻 、 靛红 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以84%的产率得到2,3-bis(4-methoxyphenyl)quinoline-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 6-arylindeno[1,2-c]quinoline derivatives

  摘要：

  A number of 6-arylindeno[1,2-c]quinoline derivatives were synthesized and evaluated for their antiproliferative activities against the growth of five cancer cell lines including human hepatocelluar carcinoma (Hep G2, Hep 3B and Hep2.2.1), non-small cell lung cancer (A549 and H1299), and normal diploid embryonic lung cell line (MRC-5). The preliminary results indicated that 9-(3-(dimethylamino) propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-2-fluoro-11H-indeno[1,2-c]quinolin-11-one (14c) was the most potent with GI(50) values of 0.61, 0.67, 0.59, and 0.72 mu M against the growth of Hep G2, Hep 3B, Hep 2.2.1, and H1299 cells, respectively. Results have also shown that 2,9-bis(3-(dimethylamino)propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-11H-indeno[1,2-c]quinolin-11-one (17), which exhibited GI(50) of 0.60 and 0.68 mu M against the growth of Hep G2 and A549, respectively, was more active than the positive topotecan and irinotecan. Compound 17 was less toxic than topotecan against the growth of normal cell (MRC-5) and therefore, was selected for further evaluation. Results indicated that compound 17 induce cell cycle arrest in G2/M phase, DNA fragmentation, and disrupt the microtubule network in A549 cells. The apoptotic induction may through the cleavage of PARP. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.021

文献信息

• Buu-Hoi et al., Bulletin de la Societe Chimique de France, 1956, p. 629,631
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Synthesis and antiproliferative evaluation of 6-arylindeno[1,2-c]quinoline derivatives
  作者：Chih-Hua Tseng、Yeh-Long Chen、Kuin-Yu Chung、Chih-Mei Cheng、Chi-Huei Wang、Cherng-Chyi Tzeng

  DOI：10.1016/j.bmc.2009.09.021

  日期：2009.11

  A number of 6-arylindeno[1,2-c]quinoline derivatives were synthesized and evaluated for their antiproliferative activities against the growth of five cancer cell lines including human hepatocelluar carcinoma (Hep G2, Hep 3B and Hep2.2.1), non-small cell lung cancer (A549 and H1299), and normal diploid embryonic lung cell line (MRC-5). The preliminary results indicated that 9-(3-(dimethylamino) propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-2-fluoro-11H-indeno[1,2-c]quinolin-11-one (14c) was the most potent with GI(50) values of 0.61, 0.67, 0.59, and 0.72 mu M against the growth of Hep G2, Hep 3B, Hep 2.2.1, and H1299 cells, respectively. Results have also shown that 2,9-bis(3-(dimethylamino)propoxy)-6-(4-(3-(dimethylamino)propoxy)phenyl)-11H-indeno[1,2-c]quinolin-11-one (17), which exhibited GI(50) of 0.60 and 0.68 mu M against the growth of Hep G2 and A549, respectively, was more active than the positive topotecan and irinotecan. Compound 17 was less toxic than topotecan against the growth of normal cell (MRC-5) and therefore, was selected for further evaluation. Results indicated that compound 17 induce cell cycle arrest in G2/M phase, DNA fragmentation, and disrupt the microtubule network in A549 cells. The apoptotic induction may through the cleavage of PARP. (C) 2009 Elsevier Ltd. All rights reserved.