2-(2,3-dioxoindolin-1-yl)-N-(4-nitrophenyl)acetamide | 302968-16-7

• 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-(4-nitrophenyl)acetamide
• 英文别名: 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-(4-nitrophenyl)acetamide；2-(2,3-dioxoindol-1-yl)-N-(4-nitrophenyl)acetamide
• CAS: 302968-16-7
• 化学式: C₁₆H₁₁N₃O₅
• 分子量: 325.28
• InChiKey: KKDJSVAOORLTRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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

• 作为反应物：
  描述：

  2-(2,3-dioxoindolin-1-yl)-N-(4-nitrophenyl)acetamide 、 氨基硫脲 在 溶剂黄146 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  N-苯乙酰胺-羟吲哚-氨基硫脲杂化物作为新的潜在酪氨酸酶抑制剂的设计、合成、体外和计算机评估

  摘要：

  合成了一系列新的N-苯基乙酰胺-羟吲哚-氨基硫脲杂化物，并评估了它们的酪氨酸酶抑制活性。根据酪氨酸酶抑制结果，与IC 50值为36.32 μM的阳性对照曲酸相比，所有合成的化合物均显示出较高的酪氨酸酶抑制活性，IC 50值为0.8至3.88 μM。在测试的化合物中，在N-苯基乙酰胺部分上含有 2-甲基-4-硝基苯基的类似物7o表现出优异的酪氨酸酶抑制作用。这种化合物的效力是曲酸的约 45 倍。化合物7o的动力学分析证明该化合物是针对酪氨酸酶的竞争性抑制剂。该化合物的对接研究表明，化合物7o与酪氨酸酶活性位点内的关键组氨酸残基相互作用。

  DOI：

  10.1002/cbdv.202100666
• 作为产物：
  描述：

  2-(Phenylamino)acetaldehyde oxime 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(2,3-dioxoindolin-1-yl)-N-(4-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。
• Structure-based Design, Synthesis, and Biological Evaluation of Isatin Derivatives as Potential Glycosyltransferase Inhibitors
  作者：Yong Wang、Fung-Yi Chan、Ning Sun、Hok-Kiu Lui、Pui-Kin So、Siu-Cheong Yan、Kin-Fai Chan、Jiachi Chiou、Sheng Chen、Ruben Abagyan、Yun-Chung Leung、Kwok-Yin Wong

  DOI：10.1111/cbdd.12361

  日期：2014.12

  biosynthesis. Structure‐based virtual screening of about 3 000 000 commercially available compounds against the crystal structure of the glycosyltransferase (GT) domain of the Staphylococcus aureus penicillin‐binding protein 2 (S. aureus PBP2) resulted in identification of an isatin derivative, 2‐(3‐(2‐carbamimidoylhydrazono)‐2‐oxoindolin‐1‐yl)‐N‐(m‐tolyl)acetamide (4) as a novel potential GT inhibitor. A series

  肽聚糖糖基转移酶（PGT）已被证明是抑制细菌细胞壁生物合成的重要药理靶标。对金黄色葡萄球菌青霉素结合蛋白2（金黄色葡萄球菌PBP2）的糖基转移酶（GT）结构域的晶体结构进行约3,000万市售化合物的基于结构的虚拟筛选，结果发现了靛红衍生物2-（ 3-（2-氨基甲酰肼基）-2-氧吲哚-1-基）-N-（间甲苯基）乙酰胺（4）作为潜在的新型GT抑制剂。合成了一系列的4种衍生物。几种化合物显示出比初始命中化合物更有效的抗菌活性4，尤其是2-（3-（2-氨基甲酰肼基）-2-氧吲哚-1-基）-N-（3-硝基苯基）乙酰胺（4l），对革兰氏阳性枯草芽孢杆菌和金黄色葡萄球菌的MIC值为24和 48μg / mL。饱和转移差异（STD）NMR研究表明，在4l和金黄色葡萄球菌PBP2的GT结构域之间存在结合接触。竞争性STD-NMR进一步证明了4l和Moenomycin A以竞争性方式与GT结构域结合。分子对接
• 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.
• Design, Synthesis, <i>in Vitro</i> , and <i>in Silico</i> Evaluation of <i>N</i> ‐Phenylacetamide‐Oxindole‐Thiosemicarbazide Hybrids as New Potential Tyrosinase Inhibitors
  作者：Shahriar Yari Boroujeni、Zahra Haghighijoo、Maryam Mohammadi‐Khanaposhtani、Ali Mosadeghkhah、Ali Moazzam、Ali Yavari、Manan Hajimahmoodi、Reyhaneh Sabourian、Samesadat Hosseini、Bagher Larijani、Halleh Hamedifar、Samira Ansari、Mohammad Mahdavi

  DOI：10.1002/cbdv.202100666

  日期：2022.4

  A novel series of N-phenylacetamide-oxindole-thiosemicarbazide hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. According to tyrosinase inhibition results, all the synthesized compounds showed high tyrosinase inhibitory activity with IC50 values ranging from 0.8 to 3.88 μM in comparison to positive control kojic acid with IC50 value of 36.32 μM. Among tested compounds

  合成了一系列新的N-苯基乙酰胺-羟吲哚-氨基硫脲杂化物，并评估了它们的酪氨酸酶抑制活性。根据酪氨酸酶抑制结果，与IC 50值为36.32 μM的阳性对照曲酸相比，所有合成的化合物均显示出较高的酪氨酸酶抑制活性，IC 50值为0.8至3.88 μM。在测试的化合物中，在N-苯基乙酰胺部分上含有 2-甲基-4-硝基苯基的类似物7o表现出优异的酪氨酸酶抑制作用。这种化合物的效力是曲酸的约 45 倍。化合物7o的动力学分析证明该化合物是针对酪氨酸酶的竞争性抑制剂。该化合物的对接研究表明，化合物7o与酪氨酸酶活性位点内的关键组氨酸残基相互作用。