4-(1,3-dioxo-hexahydro-1H-isoindol-2(3H)-yl)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide | 5769-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(1,3-dioxo-hexahydro-1H-isoindol-2(3H)-yl)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
• 英文别名: 4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
• CAS: 5769-40-4
• 化学式: C₁₉H₂₀N₄O₄S
• mdl: MFCD01819616
• 分子量: 400.458
• InChiKey: VUXQBAWBTHTARM-UHFFFAOYSA-N

物化性质

• 熔点：
  118-121 °C
• 沸点：
  440.8±55.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  磺胺甲基嘧啶 、 六氢苯酐 反应 0.03h， 以86%的产率得到4-(1,3-dioxo-hexahydro-1H-isoindol-2(3H)-yl)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Microwave-assisted synthesis of benzenesulfonohydrazide and benzenesulfonamide cyclic imide hybrid molecules and their evaluation for anticancer activity

  摘要：

  4-Methyl benzenesulfonohydrazide (1a) and 4-methoxy benzenesulfonohydrazide (1b) on condensation with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione under microwave irradiation condition gave corresponding condensation products 2a,b; 3a,b; 4a,b and 5a,b, respectively, in good yields. Microwave-assisted condensation of 4-amino-N-(thiazol-2-yl)benzenesulfonamide (6a), 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (6b) and 4-amino-N-(4-methyl pyrimidin-2-yl)benzenesulfonamide (6c) with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione gave corresponding condensation products 7a-c, 8a-c, 9a-c and 10a-c, respectively, in good yields. All these compounds, i.e., 2a,b; 3a,b; 4a,b; 5a,b; 7a-c; 8a-c; 9a-c and 10a-c, were screened for in vitro anticancer activity against five human cancer cell lines, i.e., breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1) and liver (Hep G2). Compounds 7c and 9c exhibited good anticancer activity against ovary (PA-1) (IC50 value 8.12 +/- A 1.83 A mu M) and liver (Hep G2) (IC50 value 4 +/- A 1.9 A mu M) cancer cell lines, respectively.

  DOI：

  10.1007/s00044-015-1414-9

文献信息

• Microwave-assisted synthesis of benzenesulfonohydrazide and benzenesulfonamide cyclic imide hybrid molecules and their evaluation for anticancer activity
  作者：Anuj Kumar、Nikhil Kumar、Partha Roy、S. M. Sondhi、Anuj Sharma

  DOI：10.1007/s00044-015-1414-9

  日期：2015.10

  4-Methyl benzenesulfonohydrazide (1a) and 4-methoxy benzenesulfonohydrazide (1b) on condensation with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione under microwave irradiation condition gave corresponding condensation products 2a,b; 3a,b; 4a,b and 5a,b, respectively, in good yields. Microwave-assisted condensation of 4-amino-N-(thiazol-2-yl)benzenesulfonamide (6a), 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (6b) and 4-amino-N-(4-methyl pyrimidin-2-yl)benzenesulfonamide (6c) with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione gave corresponding condensation products 7a-c, 8a-c, 9a-c and 10a-c, respectively, in good yields. All these compounds, i.e., 2a,b; 3a,b; 4a,b; 5a,b; 7a-c; 8a-c; 9a-c and 10a-c, were screened for in vitro anticancer activity against five human cancer cell lines, i.e., breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1) and liver (Hep G2). Compounds 7c and 9c exhibited good anticancer activity against ovary (PA-1) (IC50 value 8.12 +/- A 1.83 A mu M) and liver (Hep G2) (IC50 value 4 +/- A 1.9 A mu M) cancer cell lines, respectively.