N-[4-[4-(羟基氨基)苯基]磺酰基苯基]乙酰胺 | 32604-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[4-[4-(羟基氨基)苯基]磺酰基苯基]乙酰胺
• 英文名称: monoacetyldapsone hydroxylamine
• 英文别名: N-[4-[4-(hydroxyamino)phenyl]sulfonylphenyl]acetamide
• CAS: 32604-86-7
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: YUWDJHZQRAHBBW-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188°C (dec.)
• 密度：
  1.449±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-[4-[4-(羟基氨基)苯基]磺酰基苯基]乙酰胺 在 甲醇 、 碳酸氢钠 作用下， 生成 bis-[4-(N-acetyl-sulfanilyl)-phenyl]-diazene-N-oxide
  参考文献：
  名称：

  4-氨基-4'-羟基氨基二苯砜，其乙酰基和D-葡萄糖基衍生物。

  摘要：

  DOI：

  10.1021/ja01212a013
• 作为产物：
  描述：

  N-[4-(4-硝基苯基)磺酰基苯基]乙酰胺 在 platinum(IV) oxide 亚磷酸三乙酯 作用下， 反应 4.0h， 以85%的产率得到N-[4-[4-(羟基氨基)苯基]磺酰基苯基]乙酰胺
  参考文献：
  名称：

  Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes

  摘要：

  Cutaneous drug reactions (CDR) are responsible for numerous minor to life-threatening complications. Though the exact mechanism for CDR is not completely understood, evidence suggests that bioactivation of drugs to reactive oxygen or nitrogen species is an important factor in the initiation of these reactions. Several CDR-inducing drugs having an arylamine functional group, such as sulfamethoxazole (SMX) and dapsone (DDS), undergo bioactivation to reactive arylhydroxylamine metabolites. These metabolites can generate cellular oxidative stress by forming reactive oxygen species (ROS). Several studies have demonstrated a higher cytotoxicity with DDS hydroxylamine (DDS-NOH) compared to SMX hydroxylamine (SMX-NOH). To investigate the role of differential ROS generation in the higher cytotoxicity of DDS-NOH, hydroxylamine metabolites of SMX and DDS were synthesized and ROS formation by these metabolites determined. DDS-NOH and its analogues/metabolites consistently resulted in higher ROS formation as compared to SMX-NOH. However, comparison of the ROS generation and cytotoxicity of a series of arylhydroxylamine analogues of DDS did not support a simple correlation between ROS generation and cell death. Numerous ROS scavengers were found to reduce metabolite-induced ROS formation, with differences in the potency between the agents. The decrease in DDS-NOH-induced ROS generation in NHEK with ascorbic acid, N-acetylcysteine, Trolox, and melatonin was 87, 86, 44, and 16%, respectively. Similarly, the cytotoxicity and adduct formation of DDS-NOH in NHEK was reduced in the presence of ascorbic acid. In summary, these studies show that arylhydroxylamine metabolites of SMX/DDS induce ROS generation in NHEK, though such generation is not directly related to cytotoxicity. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2005.04.023

文献信息

• Owari, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 246,249
  作者：Owari

  DOI：——

  日期：——
• Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes
  作者：Piyush M. Vyas、Sanjoy Roychowdhury、Patrick M. Woster、Craig K. Svensson

  DOI：10.1016/j.bcp.2005.04.023

  日期：2005.7

  Cutaneous drug reactions (CDR) are responsible for numerous minor to life-threatening complications. Though the exact mechanism for CDR is not completely understood, evidence suggests that bioactivation of drugs to reactive oxygen or nitrogen species is an important factor in the initiation of these reactions. Several CDR-inducing drugs having an arylamine functional group, such as sulfamethoxazole (SMX) and dapsone (DDS), undergo bioactivation to reactive arylhydroxylamine metabolites. These metabolites can generate cellular oxidative stress by forming reactive oxygen species (ROS). Several studies have demonstrated a higher cytotoxicity with DDS hydroxylamine (DDS-NOH) compared to SMX hydroxylamine (SMX-NOH). To investigate the role of differential ROS generation in the higher cytotoxicity of DDS-NOH, hydroxylamine metabolites of SMX and DDS were synthesized and ROS formation by these metabolites determined. DDS-NOH and its analogues/metabolites consistently resulted in higher ROS formation as compared to SMX-NOH. However, comparison of the ROS generation and cytotoxicity of a series of arylhydroxylamine analogues of DDS did not support a simple correlation between ROS generation and cell death. Numerous ROS scavengers were found to reduce metabolite-induced ROS formation, with differences in the potency between the agents. The decrease in DDS-NOH-induced ROS generation in NHEK with ascorbic acid, N-acetylcysteine, Trolox, and melatonin was 87, 86, 44, and 16%, respectively. Similarly, the cytotoxicity and adduct formation of DDS-NOH in NHEK was reduced in the presence of ascorbic acid. In summary, these studies show that arylhydroxylamine metabolites of SMX/DDS induce ROS generation in NHEK, though such generation is not directly related to cytotoxicity. (c) 2005 Elsevier Inc. All rights reserved.
• 4-Amino-4'-hydroxylaminodiphenyl Sulfone, its Acetyl and D-Glucosyl Derivatives
  作者：Ernest L. Jackson

  DOI：10.1021/ja01212a013

  日期：1946.8