2-(p-methoxyphenyl)-3-[4-[(pyridin-2-yl)aminosulfonyl]phenyl]-2,4-dihydrobenzo[e][1,3]thiazin-4-one | 1214992-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-(p-methoxyphenyl)-3-[4-[(pyridin-2-yl)aminosulfonyl]phenyl]-2,4-dihydrobenzo[e][1,3]thiazin-4-one
• 英文别名: 4-[2-(4-methoxyphenyl)-4-oxo-2H-1,3-benzothiazin-3-yl]-N-pyridin-2-ylbenzenesulfonamide
• CAS: 1214992-24-1
• 化学式: C₂₆H₂₁N₃O₄S₂
• 分子量: 503.602
• InChiKey: SLCBBINUUITQFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-((4-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide 、 硫代水杨酸 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以72%的产率得到2-(p-methoxyphenyl)-3-[4-[(pyridin-2-yl)aminosulfonyl]phenyl]-2,4-dihydrobenzo[e][1,3]thiazin-4-one
  参考文献：
  名称：

  Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives

  摘要：

  A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff's bases) 2a-c and 4a-e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a-c with thioglycolic acid led to the formation of the C-nucleosides (3a-c), while treatment of 4a-e with thioglycolic and/or thiosalicylic acids afforded the corresponding 2-arylthiazolidin-4-one or 2-arylbenzothiazin-4-one derivatives 5a-e and/or 6a-e, respectively. Some representative examples of the newly prepared compounds showed considerable cytotoxic effect against breast carcinoma cell line MCF7 and cervix carcinoma cell line HEIA in comparison with 5-flurouracil and doxorubicin. AutoDock molecular docking into PTK has been done for lead optimization of the compounds in study as potential PTK inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.044

文献信息

• Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives
  作者：Mohsen M. Kamel、Hamed I. Ali、Manal M. Anwar、Neama A. Mohamed、AbdelMohsen M. Soliman

  DOI：10.1016/j.ejmech.2009.10.044

  日期：2010.2

  A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff's bases) 2a-c and 4a-e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a-c with thioglycolic acid led to the formation of the C-nucleosides (3a-c), while treatment of 4a-e with thioglycolic and/or thiosalicylic acids afforded the corresponding 2-arylthiazolidin-4-one or 2-arylbenzothiazin-4-one derivatives 5a-e and/or 6a-e, respectively. Some representative examples of the newly prepared compounds showed considerable cytotoxic effect against breast carcinoma cell line MCF7 and cervix carcinoma cell line HEIA in comparison with 5-flurouracil and doxorubicin. AutoDock molecular docking into PTK has been done for lead optimization of the compounds in study as potential PTK inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.