4-(2-methanesulfonyloxyethylamino)-3,5-dinitroacetanilide | 835627-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-methanesulfonyloxyethylamino)-3,5-dinitroacetanilide
• 英文别名: 2-(4-Acetamido-2,6-dinitroanilino)ethyl methanesulfonate；2-(4-acetamido-2,6-dinitroanilino)ethyl methanesulfonate
• CAS: 835627-56-0
• 化学式: C₁₁H₁₄N₄O₈S
• 分子量: 362.32
• InChiKey: GPONUPPISLPPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(2-methanesulfonyloxyethylamino)-3,5-dinitroacetanilide 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 5,7-diacetamido-1,4-diacetyl-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products

  摘要：

  The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in similar to9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.016
• 作为产物：
  描述：

  N-乙酰基-N-(4-甲氧基苯基)乙酰胺 在 吡啶 、 硝酸 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 4-(2-methanesulfonyloxyethylamino)-3,5-dinitroacetanilide
  参考文献：
  名称：

  Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products

  摘要：

  The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in similar to9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.016

文献信息

• Synthesis and Biological Evaluation of Imidazoquinoxalinones, Imidazole Analogues of Pyrroloiminoquinone Marine Natural Products
  作者：Hung Hoang、Daniel V. LaBarbera、Kaleem A. Mohammed、Chris M. Ireland、Edward B. Skibo

  DOI：10.1021/jm0700870

  日期：2007.9.1

  This report describes the synthesis and biological activity of imidazoquinoxalines, benzimidazole-based analogues of indole-based pyrroloiminoquinone marine natural products. Our analogues consist of series 1, which possesses the ethylene tether and extended amidine feature found in the pyrroloiminoquinone natural products, and series 2, which also has the ethylene tether but with an electrostatically

  该报告描述了咪唑并喹喔啉，吲哚基吡咯烷基氨基醌海洋天然产物的苯并咪唑基类似物的合成和生物活性。我们的类似物由系列1和系列2组成，系列1具有在吡咯烷氨基醌天然产物中发现的乙烯系链和idine的延伸特征，系列2也具有乙烯系链，但具有静电稳定的亚氨基醌而不是共振稳定的亚氨基醌（即，延伸的idine ）。系列1类似物的生物学特性带有富电子侧链环（吲哚和苯酚），具有与吡咯烷氨基醌天然产物相似的细胞抑制和细胞毒性特性。相反，COMPARE分析表明带有苄基和苯乙基侧链的类似物具有不同的细胞毒性机制。1的类似物的中空纤维测定表明有希望的抗肿瘤活性和可接受的毒性水平。2的一种类似物仅对乳腺癌细胞系具有活性，但细胞靶标尚不清楚。