2-(2,3-dioxoindolin-1-yl)-N-(2-nitrophenyl)acetamide | 1228425-77-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3-dioxoindolin-1-yl)-N-(2-nitrophenyl)acetamide
• 英文别名: 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(2-nitrophenyl)acetamide；2-(2,3-dioxoindol-1-yl)-N-(2-nitrophenyl)acetamide
• CAS: 1228425-77-1
• 化学式: C₁₆H₁₁N₃O₅
• 分子量: 325.28
• InChiKey: QMBWRCDHCSOYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯胺 在 盐酸 、 水合氯醛 、 硫酸 、 盐酸羟胺 、 potassium carbonate 、 sodium sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(2,3-dioxoindolin-1-yl)-N-(2-nitrophenyl)acetamide
  参考文献：
  名称：

  Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents

  摘要：

  This study deals with the synthesis of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives (6a-j) from isatin (3) and 5,7-dibromoisatin (4). All newly synthesized compounds were characterized using IR, H-1 NMR, MS, and elemental analysis followed by evaluation of their cytotoxic activity by XTT assay on breast cancer cell line MCF-7 and non-cancer African green monkey cell line VERO. Correlation study for QSAR and in vitro assay was performed. The outcomes indicated that electron withdrawing substitutions at para position of phenyl ring and 5, 7 positions of isatin ring and increasing lipophilicity of the compound increased the cytotoxic activity. The 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(4-nitrophenyl)acetamide (6b) was found to be the most active compound in the series and demonstrated higher selectivity toward MCF-7 cell line. The IC50 values were 1.96 and 1.90 mu M for test compound (6b) and vinblastin (reference drug), respectively. This indicates compound (6b) may possess equipotent cytotoxic activity to vinblastine. The compound (6b) is particularly promising, since it could kill cancer cells 19-20 times more effectively than the non-cancer cells. This property of (6b) may enable us to effectively control tumors with low side effects. Hence, we propose that 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H- indol-1-yl)-N-(4-nitrophenyl)acetamide may be used as lead for further development.

  DOI：

  10.1007/s00044-010-9361-y

文献信息

• Efficient synthesis, biological evaluation, and docking study of isatin based derivatives as caspase inhibitors
  作者：Loghman Firoozpour、Lixin Gao、Setareh Moghimi、Parvin Pasalar、Jamshid Davoodi、Ming-Wei Wang、Zahra Rezaei、Armin Dadgar、Hoda Yahyavi、Massoud Amanlou、Alireza Foroumadi

  DOI：10.1080/14756366.2020.1809388

  日期：2020.1.1

  In this paper, a new series of isatin-sulphonamide based derivatives were designed, synthesised and evaluated as caspase inhibitors. The compounds containing 1-(pyrrolidinyl)sulphonyl and 2-(phenoxymethyl)pyrrolidin-1-yl)sulphonyl substitution at C5 position of isatin core exhibited better results compared to unsubstituted derivatives. According to the results of caspase inhibitory activity, compound

  在本文中，设计，合成和评估了一系列新的基于isatin-sulphonamide的衍生物作为胱天蛋白酶抑制剂。与未取代的衍生物相比，在靛红核的C5位上含有1-（吡咯烷基）磺酰基和2-（苯氧基甲基）吡咯烷-1-基）磺酰基取代的化合物表现出更好的结果。根据caspase抑制活性的结果，与Ac-DEVD-CHO相比，化合物20d在体外显示出对caspase-3和-7的中等抑制活性（IC 50 = 0.016±0.002μM）。在研究的化合物中，鉴定出一些活性抑制剂，IC 50值在2.33–116.91μM之间。化合物20d的活性通过分子建模研究使之合理化，该研究展示了N-苯基乙酰胺取代的额外范德华相互作用以及有效的T形π-π和π-阳离子相互作用。具有良好的半胱天冬酶抑制活性的化合物20d的引入将有助于研究人员寻找更有效的药物。
• Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents
  作者：Neha R. Modi、Ravi J. Shah、Manish J. Patel、Maulik Suthar、Bhupendrasinh F. Chauhan、Laxmanbhai J. Patel

  DOI：10.1007/s00044-010-9361-y

  日期：2011.6

  This study deals with the synthesis of novel 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives (6a-j) from isatin (3) and 5,7-dibromoisatin (4). All newly synthesized compounds were characterized using IR, H-1 NMR, MS, and elemental analysis followed by evaluation of their cytotoxic activity by XTT assay on breast cancer cell line MCF-7 and non-cancer African green monkey cell line VERO. Correlation study for QSAR and in vitro assay was performed. The outcomes indicated that electron withdrawing substitutions at para position of phenyl ring and 5, 7 positions of isatin ring and increasing lipophilicity of the compound increased the cytotoxic activity. The 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(4-nitrophenyl)acetamide (6b) was found to be the most active compound in the series and demonstrated higher selectivity toward MCF-7 cell line. The IC50 values were 1.96 and 1.90 mu M for test compound (6b) and vinblastin (reference drug), respectively. This indicates compound (6b) may possess equipotent cytotoxic activity to vinblastine. The compound (6b) is particularly promising, since it could kill cancer cells 19-20 times more effectively than the non-cancer cells. This property of (6b) may enable us to effectively control tumors with low side effects. Hence, we propose that 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H- indol-1-yl)-N-(4-nitrophenyl)acetamide may be used as lead for further development.