2,9-dimethyl-5-(1-methyl-1H-pyrrol-2-yl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]-quinolin-4-one | 1610691-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,9-dimethyl-5-(1-methyl-1H-pyrrol-2-yl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]-quinolin-4-one
• CAS: 1610691-39-8
• 化学式: C₁₈H₂₀N₄O
• 分子量: 308.383
• InChiKey: UGEJMUMCJAFEEH-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  487.3±55.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.57
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-甲基环己酮 在 硫酸 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 2,9-dimethyl-5-(1-methyl-1H-pyrrol-2-yl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]-quinolin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel tetrahydroquinolines as anticancer and antimicrobial agents

  摘要：

  This study reports the synthesis of a series of new 2-amino-3-cyano-8-methyl-4-substituted-5,6,7,8-tetrahydroquinolines along with some derived fused-ring systems. Ten compounds have shown remarkable cytotoxic activity against human colon carcinoma HT29, hepatocellular carcinoma HepG2 and Caucasian breast adenocarcinoma MCF7 cell lines. Six compounds showed considerable broad-spectrum cytotoxic activity among which two proved to be the most active derivatives. Likewise, seven compounds from the series were found to exhibit significant antimicrobial activity and three of them proved to be the most active candidates. Two alkylthio-pyrimido quinolines are suggested as possible antimicrobial and anticancer candidates in the present series.

  DOI：

  10.3109/14756366.2013.787421

文献信息

• Microwave-assisted synthesis of certain pyrrolylpyridines, some derived ring systems and their evaluation as anticancer and antioxidant agents
  作者：Sherif A.F. Rostom、Adnan A. Bekhit

  DOI：10.1016/j.ejmech.2015.01.023

  日期：2015.3

  The synthesis of 18 novel pyrrolylpyridines and some derived bi-, tri- and tetracyclic ring systems using both the conventional heating and MW irradiation techniques is described. Fourteen compounds; 2-9, 10-12, 14, 17 and 18 were evaluated for their antitumor activity according to the National Cancer Institute (NCI), in vitro disease oriented antitumor screening. Distinctive antitumor activity was conjugated with compounds 3 and 7 (R = 3,4-di-OCH3-C6H3). The analogs 3, 6, 7, 9, 10, 11 and 12 which exhibited prominent antitumor activity, were further evaluated for their antioxidant potential using the DPPH radical scavenging assay. The substituted 6-(3,4-dimethoxyphenyl)pyridine-3-carbonitriles 3 and 7 were nearly equipotent to BHT the standard antioxidant utilized in this assay (scavenging activity 31 and 33%, respectively, vs 36%). Accordingly, compounds 3 and 7 can be considered as lead structures for dual antitumor and antioxidant activities. (C) 2015 Elsevier Masson SAS. All rights reserved.