N-cyclohexyl-2-(4-(dimethylamino)phenyl)imidazo[1,2-a]pyridin-3-amine | 931722-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-cyclohexyl-2-(4-(dimethylamino)phenyl)imidazo[1,2-a]pyridin-3-amine
• 英文别名: N-cyclohexyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyrazin-3-amine
• CAS: 931722-15-5
• 化学式: C₂₀H₂₅N₅
• 分子量: 335.452
• InChiKey: KZBPTUOHSFKLTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氨基吡嗪 、 异氰环已烷 、 对二甲氨基苯甲醛 在 calcium(II) trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以89%的产率得到N-cyclohexyl-2-(4-(dimethylamino)phenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Design, synthesis and anticancer activity of 2-arylimidazo[1,2-a]pyridinyl-3-amines

  摘要：

  A series of imido-heterocycle compounds were designed, synthesized, characterized, and evaluated for the anticancer potential using breast (MCF-7 and MDA-MB-231), pancreatic (PANC-1), and colon (HCT-116 and HT-29) cancer cell lines and normal cells, while normal cells showed no toxicity. Among the screened compounds, 4h exhibited the best anticancer potential with IC50 values ranging from 1 to 5.5 μM. Compound 4h caused G2/M phase arrest and apoptosis in all the cell lines except MDA-MB-231 mammosphere formation was inhibited. In-vitro enzyme assay showed selective topoisomerase IIα inhibition by compound 4h, leading to DNA damage as observed by fluorescent staining. Cell signalling studies showed decreased expression of cell cycle promoting related proteins while apoptotic proteins were upregulated. Interestingly MDA-MB-231 cells showed only cytostatic effects upon treatment with compound 4h due to defective p53 status. Toxicity study using overexpression of dominant-negative mutant p53 in MCF-7 cells (which have wild type functional p53) showed that anticancer potential of compound 4h is positively correlated with p53 expression.

  DOI：

  10.1016/j.bioorg.2021.105464

文献信息

• [EN] SMALL MOLECULE INHIBITION OF TRANSCRIPTION FACTOR SALL4 AND USES THEREOF<br/>[FR] INHIBITION PAR DES PETITES MOLÉCULES DU FACTEUR DE TRANSCRIPTION SALL4 ET SES UTILISATIONS
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2019070943A1

  公开（公告）日：2019-04-11

  Provided herein are compounds that interrupt the function of SALL4. Also described are pharmaceutical compositions and medical uses of these compounds.

  本文提供了一些干扰SALL4功能的化合物。同时还描述了这些化合物的药物组合物和医疗用途。
• Small molecule inhibition of transcription factor SALL4 and uses thereof
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US11530209B2

  公开（公告）日：2022-12-20

  Provided herein are compounds that interrupt the function of SALL4. Also described are pharmaceutical compositions and medical uses of these compounds.

  本文提供了能干扰 SALL4 功能的化合物。还描述了这些化合物的药物组合物和医疗用途。
• SMALL MOLECULE INHIBITION OF TRANSCRIPTION FACTOR SALL4 AND USES THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20200317664A1

  公开（公告）日：2020-10-08

  Provided herein are compounds that interrupt the function of SALL4. Also described are pharmaceutical compositions and medical uses of these compounds.