3-(2-喹喔啉基亚甲基)肼基甲酸甲酯 | 55456-55-8

• 物质功能分类: 分析化学 - 标准品 - 法医和兽医标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-(2-喹喔啉基亚甲基)肼基甲酸甲酯
• 中文别名: 脱氧卡巴氧/脱氧卡巴多司；脱氧卡巴氧
• 英文名称: methyl 3-(2-quinoxalinylmethylene)carbazate
• 英文别名: quinoxalin-2-ylmethylene-hydrazinecarboxylic acid methyl ester；Desoxycarbadox；methyl N-(quinoxalin-2-ylmethylideneamino)carbamate
• CAS: 55456-55-8
• 化学式: C₁₁H₁₀N₄O₂
• 分子量: 230.226
• InChiKey: SOEMFPLGOUBPJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  232-236 °C(Solv: toluene (108-88-3); ethanol (64-17-5))
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  F,T
• 安全说明：
  S45,S53
• 危险类别码：
  R45,R11,R22
• WGK Germany：
  3

制备方法与用途

生物活性

Desoxycarbadox 是 Carbadox（HY-B1340）的代谢产物。Carbadox 是一种喹喔啉二氮氧化物抗生素化合物。

体内研究

Desoxycarbadox 在大鼠中的瘤形成活性中扮演着重要角色。

反应信息

• 作为产物：
  描述：

  卡巴多 在 盐酸 、 titanium(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以94%的产率得到3-(2-喹喔啉基亚甲基)肼基甲酸甲酯
  参考文献：
  名称：

  Applications of TiCl₃ as a Diagnostic Reagent for the Detection of Nitro- and N-Oxide-Containing Compounds as Potentially Mutagenic Impurities Using Ultrahigh-Performance Liquid Chromatography Coupled with High-Resolution Mass Spectrometry

  摘要：

  The ICH has strict guidelines for limiting the presence of potentially mutagenic impurities (PMIs) in marketed drugs. Therefore, it is important to fully characterize and quantitate all possible PMIs that could arise during the process of synthesizing and developing a drug. Two important and prevalent examples of PMIs are compounds containing N-oxide and nitro functional groups. TiCl3 derivatization is an established method for determining the presence or absence of N-oxide metabolites by reduction to the corresponding amine. In this study, we demonstrate a novel application of TiCl3 reduction combined with high-resolution UHPLC/HRMS to analyze PMIs. The results indicate that a variety of N-oxide- and nitro-containing compounds can be readily characterized by this facile platform method. In addition, we show that this chemical derivatization method can be utilized to enhance the ionization of nitro-containing compounds for LC/MS analysis.

  DOI：

  10.1021/acs.oprd.5b00312

文献信息

• Selective Monodeoxygenation of Methyl 3-(2-Quinoxalinylmethylene)carbazate N1, N4-Dioxide (Carbadox)
  作者：D. J. R. Massy、A. McKillop

  DOI：10.1055/s-1996-4420

  日期：1996.12

  The veterinary drug methyl 3-(2-quinoxalinylmethylene)carbazate N 1, N 4-dioxide (Carbadox) has been selectively reduced in good yield at either N 1 or N 4 with the reagents sodium dithionite or phosphorus trichloride, respectively. The identity of the products, which are important metabolites, was established by 1H NMR and by an X-ray crystal structure of the N 1-monodeoxygenated product. The further metabolite, bis(desoxy) Carbadox, was prepared by reduction of Carbadox with a slight excess of sodium dithionite/acetic acid. When a large excess of this reagent was used, a new compound, methyl 3-(2-quinoxalinylmethyl)carbazate, was also formed.

  兽药 3-(2-喹喔啉基亚甲基)咔唑酸甲酯 N 1、N 4-二氧化物（Carbadox）分别在 N 1 或 N 4 处用二亚硫酸钠或三氯化磷试剂进行了选择性还原，收率很高。通过 1H NMR 和 N 1-单脱氧产物的 X 射线晶体结构，确定了重要代谢产物的身份。另一种代谢物--双（脱氧）卡巴多，是用少量过量的二亚硫酸钠/乙酸还原卡巴多制备的。当使用大量过量的这种试剂时，还会生成一种新的化合物，即 3-(2-喹喔啉基甲基)咔唑酸甲酯。