3-hydroxy-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one | 441746-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one
• 英文别名: 3-hydroxy-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethyl]indol-2-one
• CAS: 441746-25-4
• 化学式: C₁₇H₁₄N₂O₅
• 分子量: 326.309
• InChiKey: YUKLIBYIOFJUNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 1-methyl-3-[(E)-2-(4-nitro-phenyl)-2-oxo-ethylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

  摘要：

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.056
• 作为产物：
  描述：

  1-甲基靛红 、 对硝基苯乙酮 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 3-hydroxy-1-methyl-3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

  摘要：

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.056