N-[(4-氨基苯基)磺酰基]-N-(5-甲基异恶唑-3-基)乙酰胺 | 18607-98-2

• 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-氨基苯基)磺酰基]-N-(5-甲基异恶唑-3-基)乙酰胺
• 英文名称: sulfamethoxazole
• 英文别名: N(1)-Acetylsulfamethoxazole；N-(4-aminophenyl)sulfonyl-N-(5-methyl-1,2-oxazol-3-yl)acetamide
• CAS: 18607-98-2
• 化学式: C₁₂H₁₃N₃O₄S
• 分子量: 295.319
• InChiKey: WOTJLXVSBKKTTH-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  532.9±60.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N-[(4-氨基苯基)磺酰基]-N-(5-甲基异恶唑-3-基)乙酰胺 、 荧光胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以15%的产率得到5-(2-carboxyphenyl)-5-hydroxy-1-<4-(5-methylisoxazolyl-N-acetylsulfamoyl)phenyl>-2-pyrrolin-4-one
  参考文献：
  名称：

  Studies on the fluorescence characteristics of fluorescamine derivatives.

  摘要：

  研究了丁胺、苄胺、对甲氧基苯胺、对甲苯胺、苯胺、对氯苯胺、磺胺、磺胺甲氧嗪和 N1-乙酰磺胺甲氧嗪的荧光胺衍生物的分离及其各种荧光特性，即溶剂、取代基和 pH 的影响，有机溶剂中的氢键，转化为非荧光内酯，以及薄层色谱行为。

  DOI：

  10.1248/cpb.29.2283
• 作为产物：
  描述：

  N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide; silver salt 在 铂 氢气 作用下， 以 吡啶 、 乙醇 为溶剂， 生成 N-[(4-氨基苯基)磺酰基]-N-(5-甲基异恶唑-3-基)乙酰胺
  参考文献：
  名称：

  Fujimoto,M.; Okabe,K., Chemical and pharmaceutical bulletin, 1962, vol. 10, p. 572 - 575

  摘要：

  DOI：

文献信息

• Insights into the electrochemical degradation of sulfamethoxazole and its metabolite by Ti/SnO2-Sb/Er-PbO2 anode
  作者：Yanping Wang、Chengzhi Zhou、Jinhua Wu、Junfeng Niu

  DOI：10.1016/j.cclet.2020.03.073

  日期：2020.10

  Electrochemical degradation of sulfamethoxazole (SMX) and its metabolite acetyl-sulfamethoxazole (Ac-SMX) by Ti/SnO2-Sb/Er-PbO2 were investigated. Results indicated that the electrochemical degradation of SMX and Ac-SMX followed pseudo-first-order kinetics. The rate constants of SMX and Ac-SMX were 0.268 and 0.072 min(-1) at optimal current density of 10 and 14 mA/cm(2), respectively. Transformation products of SMX and Ac-SMX were identified and the possible degradation pathways, including the cleavage of S-N bond, opening ring of isoxazole and nitration of amino group, were proposed. Total organic carbon removal of SMX was nearly 63.2% after 3 h electrochemical degradation. 22.4% nitrogen of SMX was transformed to NO3-, and 98.8% sulfur of SMX was released as SO42-. According to quantitative structure-activity relationship model, toxicities of SMX and Ac-SMX to aquatic organisms significantly decreased after electrochemical degradation. Electric energy consumption for 90% SMX and Ac-SMX degradation was determined to be 0.58-8.97 and 6.88-44.19 Wh/L at different experimental conditions, respectively. Compared with parent compound SMX, the metabolite Ac-SMX is more refractory and toxic, which emphasizes the importance of taking its metabolites into account when investigating the disposal of pharmaceuticals from wastewater. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.