2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole | 351995-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole
• 英文别名: N-[5-amino-2-(5-amino-7-bromo-4-chlorobenzotriazol-2-yl)-4-methoxyphenyl]acetamide
• CAS: 351995-07-8
• 化学式: C₁₅H₁₄BrClN₆O₂
• 分子量: 425.672
• InChiKey: HLDQJHAXRNEPPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2-acethylamino-4-amino-5-methoxyphenyl)-6-amino-4-bromo-2H-benzotriazole 、 5-amino-2-[(2-bromo-4,6-dinitrophenyl)azo]-5-amino-4-methoxyacetanilide 在 铁粉 、 magnesium chloride sodium dithionite 、 sodium hypochlorite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole
  参考文献：
  名称：

  Identification of 2-[2-(acetylamino)-4-amino-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-4) as a potent mutagen in river water in Kyoto and Aichi prefectures, Japan

  摘要：

  We have previously isolated five mutagens in blue rayon-adsorbed substances from water at a site below sewage plants in the Nishitakase River, in Kyoto, Japan, and identified two of them as 2-phenylbenzotriazole derivatives, 2-[2-(acetylamino)-4-[bis(2- methoxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-3-chloro-2H-benzotriazole (PBa-1) and 2-[2-(acetylamino)-4- [(2-cyanoethyl)ethylamino]-5- methoxyphenyl]-5- amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-2). In the present study, we collected adsorbed materials on blue cotton (3 kg x 9 times) at the same location, and isolated a sufficient amount (97 mug) of one of the remaining three mutagens other than PBTA-1 and PBTA-2, for structural analysis, by multiple column chromatography. The structure of mutagen, accounting for 12% of the total mutagenicity of the blue rayon-adsorbed substances, was determined to be a PBTA-1 analogue, 2-[2-(acetylamino)-4-amino-5-methoxyphen -5-amino-7-bromo-4chloro-2H-benzotriazole (PBTA-4). PBTA-4 is a potent mutagen, inducing 190,000 and 7,800,000 revertants of Salmonella typhimurium TA98 and YG1024 per microgram, respectively, in the presence of S9 mix. In addition to the water of the Nishitakase River, PBTA-4 was detected in water samples from two rivers that flow through other regions where textile-dyeing industries have been developed. Like other PBTA analogues, PBTA-4 might also be produced from azo dyes during industrial processes in dyeing factories and treatment at sewage plants. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(01)00147-4