2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile
• 英文别名: 2-Chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile；2-chloro-4-pyridin-3-yl-5,6,7,8-tetrahydroquinoline-3-carbonitrile
• 化学式: C₁₅H₁₂ClN₃
• 分子量: 269.733
• InChiKey: JYRPSSHLWQDHPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile 在 吡啶 、 sodium 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以86%的产率得到5-(pyridin-3-yl)-6,7,8,9-tetrahydropyrimido[4,5-b]quinoline-2,4-diamine
  参考文献：
  名称：

  Synthesis and anticancer activity of novel tetrahydroquinoline and tetrahydropyrimidoquinoline derivatives

  摘要：

  A series of new tetrahydroquinolines with different substituents at C-2 and C-4 positions in addition to several tetrahydropyrimidoquinolin-4-amines and tetrahydropyrimidoquinoline-2,4-diamines were synthesized. The in vitro anticancer activity of all newly synthesized compounds was tested against human colon carcinoma (HCT116) and human breast adenocarcinoma (MCF7) cell lines. Seven compounds 1a, 5a, 5b, 6a, 6b, 7a and 7b showed potent anticancer activity against both HCT116 and MCF7 cell lines with IC50 between 16.33 and 34.28 mu M. All these compounds were more potent than imatinib (IC50 = 34.40 mu M) and tamoxifen (IC50 = 34.30 mu M). Compound 7b was the most active against HCT116 cell line with 2.1-fold more potent antitumor activity than imatinib. Also, compounds 1a, 5b and 6a exhibited the highest anticancer activity against MCF7 cell line, having two- to 1.79-fold more potent anticancer activity than tamoxifen.

  DOI：

  10.1007/s00044-015-1388-7
• 作为产物：
  描述：

  2-oxo-4-(pyridin-3-yl)-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 反应 10.0h， 以68%的产率得到2-chloro-4-(pyridin-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Synthesis and anticancer activity of novel tetrahydroquinoline and tetrahydropyrimidoquinoline derivatives

  摘要：

  A series of new tetrahydroquinolines with different substituents at C-2 and C-4 positions in addition to several tetrahydropyrimidoquinolin-4-amines and tetrahydropyrimidoquinoline-2,4-diamines were synthesized. The in vitro anticancer activity of all newly synthesized compounds was tested against human colon carcinoma (HCT116) and human breast adenocarcinoma (MCF7) cell lines. Seven compounds 1a, 5a, 5b, 6a, 6b, 7a and 7b showed potent anticancer activity against both HCT116 and MCF7 cell lines with IC50 between 16.33 and 34.28 mu M. All these compounds were more potent than imatinib (IC50 = 34.40 mu M) and tamoxifen (IC50 = 34.30 mu M). Compound 7b was the most active against HCT116 cell line with 2.1-fold more potent antitumor activity than imatinib. Also, compounds 1a, 5b and 6a exhibited the highest anticancer activity against MCF7 cell line, having two- to 1.79-fold more potent anticancer activity than tamoxifen.

  DOI：

  10.1007/s00044-015-1388-7

文献信息

• Synthesis and anticancer activity of novel tetrahydroquinoline and tetrahydropyrimidoquinoline derivatives
  作者：Ehab M. Gedawy、Asmaa E. Kassab、Afaf A. El-Malah

  DOI：10.1007/s00044-015-1388-7

  日期：2015.9

  A series of new tetrahydroquinolines with different substituents at C-2 and C-4 positions in addition to several tetrahydropyrimidoquinolin-4-amines and tetrahydropyrimidoquinoline-2,4-diamines were synthesized. The in vitro anticancer activity of all newly synthesized compounds was tested against human colon carcinoma (HCT116) and human breast adenocarcinoma (MCF7) cell lines. Seven compounds 1a, 5a, 5b, 6a, 6b, 7a and 7b showed potent anticancer activity against both HCT116 and MCF7 cell lines with IC50 between 16.33 and 34.28 mu M. All these compounds were more potent than imatinib (IC50 = 34.40 mu M) and tamoxifen (IC50 = 34.30 mu M). Compound 7b was the most active against HCT116 cell line with 2.1-fold more potent antitumor activity than imatinib. Also, compounds 1a, 5b and 6a exhibited the highest anticancer activity against MCF7 cell line, having two- to 1.79-fold more potent anticancer activity than tamoxifen.