1-(xanthotoxin-4-sulfonamido)-4-nitrobenzene | 72454-81-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-(xanthotoxin-4-sulfonamido)-4-nitrobenzene
• 英文别名: 9-methoxy-N-(4-nitrophenyl)-7-oxo-7H-furo[3,2-g]chromene-4-sulfonamide；9-methoxy-N-(4-nitrophenyl)-7-oxofuro[3,2-g]chromene-4-sulfonamide
• CAS: 72454-81-0
• 化学式: C₁₈H₁₂N₂O₈S
• 分子量: 416.368
• InChiKey: ITCTUEAHZNUPHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(xanthotoxin-4-sulfonamido)-4-nitrobenzene 、 硫酸二甲酯 生成 9-methoxy-N-methyl-N-(4-nitrophenyl)-7-oxofuro[3,2-g]chromene-4-sulfonamide
  参考文献：
  名称：

  ATTIA A.; ISLAM A. M.; EL-MAGHRABY A. M.; AMMAR Y., INDIAN J. CHEM., 1979, B 18, NO 3, 289-290

  摘要：

  DOI：
• 作为产物：
  描述：

  xanthotoxin-4-sulfonyl chloride 、 对苯二胺 在 吡啶 、 氧气 作用下， 以 苯 为溶剂， 反应 3.0h， 以23%的产率得到1-(xanthotoxin-4-sulfonamido)-4-nitrobenzene
  参考文献：
  名称：

  New Types of Mono and Bis Sulfonamides, Tosylamino Acids and Thiosulfonic Ester Derived from Xanthotoxin, Bergapten and Visnagin with Biological Interest

  摘要：

  Xanthotoxin, bergapten, and visnagin sulfonyl chlorides have been reacted with diamines, hydrazine, amino acides, and imidazolidineiminothiones to produce the corresponding mono-, bis-sulfonamide, and tosylamino acid derivatives. Interaction of xanthotoxin-4-sulfonyl chloride with thiohydantoin furnished the respective thiosulfonic ester. The new products exhibited better antibacterial and antifungal activities.

  DOI：

  10.1080/10426500701263521

文献信息

• Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study
  作者：Bang-Le Zhang、Cheng-Qi Fan、Lei Dong、Fang-Dao Wang、Jian-Min Yue

  DOI：10.1016/j.ejmech.2010.08.045

  日期：2010.11

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.
• ATTIA A.; ISLAM A. M.; EL-MAGHRABY A. M.; AMMAR Y., J. PRAKT. CHEM., 1979, 321, NO 6, 1039-1046
  作者：ATTIA A.、 ISLAM A. M.、 EL-MAGHRABY A. M.、 AMMAR Y.

  DOI：——

  日期：——
• New Types of Mono and Bis Sulfonamides, Tosylamino Acids and Thiosulfonic Ester Derived from Xanthotoxin, Bergapten and Visnagin with Biological Interest
  作者：A. M. Sh. El-Sharief、S. Y. Al-Raqa

  DOI：10.1080/10426500701263521

  日期：2007.6.1

  Xanthotoxin, bergapten, and visnagin sulfonyl chlorides have been reacted with diamines, hydrazine, amino acides, and imidazolidineiminothiones to produce the corresponding mono-, bis-sulfonamide, and tosylamino acid derivatives. Interaction of xanthotoxin-4-sulfonyl chloride with thiohydantoin furnished the respective thiosulfonic ester. The new products exhibited better antibacterial and antifungal activities.
• ATTIA A.; ISLAM A. M.; EL-MAGHRABY A. M.; AMMAR Y., INDIAN J. CHEM., 1979, B 18, NO 3, 289-290
  作者：ATTIA A.、 ISLAM A. M.、 EL-MAGHRABY A. M.、 AMMAR Y.

  DOI：——

  日期：——