N-异丙基-alpha-(2-甲基肼基)-4-甲苯甲酰胺 | 20566-17-0

• 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-异丙基-alpha-(2-甲基肼基)-4-甲苯甲酰胺
• 英文名称: p-formyl-N-isopropylbenzamide methylhydrazone
• 英文别名: 4-[(methylhydrazinylidene)methyl]-N-propan-2-ylbenzamide
• CAS: 20566-17-0
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: ZKXUJSSMXLQPIK-UHFFFAOYSA-N

物化性质

• 沸点：
  393.9±34.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为产物：
  描述：

  甲基苄肼 在 4-(1,1-二甲基乙基)-3,5-环己二烯-1,2-二酮 、 氧气 、 tyrosinase 作用下， 生成 N-异丙基-alpha-(2-甲基肼基)-4-甲苯甲酰胺 、 4-(甲基偶氮基甲基)-N-丙-2-基苯甲酰胺
  参考文献：
  名称：

  Indirect oxidation of the antitumor agent procarbazine by tyrosinase—Possible application in designing anti-melanoma prodrugs

  摘要：

  The interaction of tyrosinase with the anticancer drug procarbazine has been investigated. In the presence of the enzyme alone no oxidation of this dialkylhydrazine above the background level was observed. However, when phenolic substrates (4-tert-butylcatechol or N-acetyl-L-tyrosine) were included in the reaction mixture, procarbazine was rapidly degraded. Oxygen consumption measurements showed that in a mixture both the phenolic substrate and the drug were oxidized. The major product of procarbazine degradation was isolated and identified as azoprocarbazine, the first active metabolite of this drug detected in previous in vivo and in vitro studies. This indirect oxidation of the hydrazine group in this anticancer agent indicates possible application of a hydrazine linker in construction of tyrosinase-activated anti-melanoma prodrugs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.041

文献信息

• Indirect oxidation of the antitumor agent procarbazine by tyrosinase—Possible application in designing anti-melanoma prodrugs
  作者：Beata Gąsowska-Bajger、Hubert Wojtasek

  DOI：10.1016/j.bmcl.2008.04.041

  日期：2008.6

  The interaction of tyrosinase with the anticancer drug procarbazine has been investigated. In the presence of the enzyme alone no oxidation of this dialkylhydrazine above the background level was observed. However, when phenolic substrates (4-tert-butylcatechol or N-acetyl-L-tyrosine) were included in the reaction mixture, procarbazine was rapidly degraded. Oxygen consumption measurements showed that in a mixture both the phenolic substrate and the drug were oxidized. The major product of procarbazine degradation was isolated and identified as azoprocarbazine, the first active metabolite of this drug detected in previous in vivo and in vitro studies. This indirect oxidation of the hydrazine group in this anticancer agent indicates possible application of a hydrazine linker in construction of tyrosinase-activated anti-melanoma prodrugs. (C) 2008 Elsevier Ltd. All rights reserved.