2-(5,7-dibromo-2,3-dioxoindolin-1-yl)-N-phenylacetamide | 1228425-56-6

• 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-(5,7-dibromo-2,3-dioxoindolin-1-yl)-N-phenylacetamide
• 英文别名: 2-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-N-phenylacetamide；2-(5,7-dibromo-2,3-dioxoindol-1-yl)-N-phenylacetamide
• CAS: 1228425-56-6
• 化学式: C₁₆H₁₀Br₂N₂O₃
• 分子量: 438.075
• InChiKey: VNNPNBVSQNSJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,4-二溴苯胺 在 盐酸 、 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-(5,7-dibromo-2,3-dioxoindolin-1-yl)-N-phenylacetamide
  参考文献：
  名称：

  Structure-based design, synthesis, and anticonvulsant activity of isatin-1-N-phenylacetamide derivatives

  摘要：

  In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of > 1,000 mg/kg, a higher protective index (PI = TD50/ED50, > 11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore.

  DOI：

  10.1007/s00044-013-0811-1

文献信息

• [EN] DIHYDRO-SPIRO[INDOLINE-3:1'-ISOQUINOLIN]-2-ONES AND THEIR ANALOGUES AND DERIVATIVES AND METHODS OF TREATING CANCER AND OTHER DISEASES<br/>[FR] DIHYDRO-SPIRO[INDOLINE-3:1'-ISOQUINOLÉIN]-2-ONES ET LEURS ANALOGUES ET DÉRIVÉS ET MÉTHODES DE TRAITEMENT DU CANCER ET D'AUTRES MALADIES
  申请人：THE UNIV OF BUEA

  公开号：WO2020183307A1

  公开（公告）日：2020-09-17

  The present invention is directed to various 3',4'-dihydro-2'H-spiro[indoline-3:1'-isoquinolin]-2-one compounds and methods for treating disease states and/or conditions which are mediated through sphingosine-1-phosphate receptor(s). The present invention is also directed to the use of these compounds as anticancer agents and as modulators of sphingosine-1-phosphate receptor function in the treatment of disease states and/or conditions which are mediated through these receptors. In addition, the invention relates to pharmaceutical compositions comprising one or more of these compounds alone or in combination with other therapeutic agents. The invention is also directed to methods of treatment of cancer and/or conditions that may respond to the modulation of sphingosine-1-phospate receptor function and which employ compounds of the present invention or pharmaceutical compositions comprising one or more of the compounds of this invention.

  本发明涉及各种3',4'-二氢-2'H-螺[吲哚啉-3:1'-异喹啉]-2-酮化合物以及治疗经过鞘氨醇-1-磷酸受体介导的疾病状态和/或病况的方法。本发明还涉及将这些化合物用作抗癌剂以及在治疗经过这些受体介导的疾病状态和/或病况中调节鞘氨醇-1-磷酸受体功能。此外，本发明涉及包含这些化合物中的一个或多个的药物组合物，单独或与其他治疗剂联合使用。本发明还涉及治疗癌症和/或可能对鞘氨醇-1-磷酸受体功能调节产生反应的病况的方法，该方法使用本发明的化合物或包含本发明中的一个或多个化合物的药物组合物。
• 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.
• Structure-based design, synthesis, and anticonvulsant activity of isatin-1-N-phenylacetamide derivatives
  作者：Chao Xie、Li-Ming Tang、Fu-Nan Li、Li-Ping Guan、Cheng-Yan Pan、Si-Hong Wang

  DOI：10.1007/s00044-013-0811-1

  日期：2014.5

  In an effort to develop the potent anticonvulsant agents, a series of novel isatin-1-N-phenylacetamide derivatives was synthesized and screened for their in vivo anticonvulsant activity against maximal electroshock test and evaluated for their neurotoxicity by the rotarod test at the same dose levels. Ten compounds exhibited the anticonvulsant activity. 2-(5-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide (4b) was found to be the most potent compound of the series with an ED50 of 91.3 mg/kg, TD50 of > 1,000 mg/kg, a higher protective index (PI = TD50/ED50, > 11) was gained than the reference drug phenobarbital and carbamazepine. The essential structural features responsible for interaction with receptor site are established within a suggested pharmacophore.