1-Amino-4-{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione N-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Amino-4-{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione N-oxide
• 英文别名: 1-amino-4-(2-dimethylamino-ethylamino)-5,8-dihydroxy-anthraquinone-1-N-oxide；2-[(4-amino-5,8-dihydroxy-9,10-dioxoanthracen-1-yl)amino]-N,N-dimethylethanamine oxide
• 化学式: C₁₈H₁₉N₃O₅
• 分子量: 357.366
• InChiKey: YJZKVEPTNRKXRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,4-二氟-5,8-二羟基蒽醌 在 吡啶 、 氨 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 1-Amino-4-{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione N-oxide
  参考文献：
  名称：

  A large-scale synthesis of the bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)

  摘要：

  我们开发了一种大规模合成双生物还原药物 1,4-双{[2-（二甲基氨基）乙基]氨基}-5,8-二羟基蒽-9,10-二酮双-N-氧化物（AQ4N）的方法。这种六步合成法能以容易获得的四氯邻苯二甲酸酐为原料合成 AQ4N，总收率为 20%。关键步骤是在 KF-NaF 介导下将 3,6-二氯邻苯二甲酸酐转化为 3,6-二氟邻苯二甲酸酐，在 100 克的规模上产率为 77%。通过 LC-MS 和独立合成）确定 AQ4N 中的痕量杂质为 1-氨基-4-[2-（二甲基氨基）乙基]氨基-5,8-二羟基蒽-9,10-二酮 N-氧化物。在多种条件下，包括在反相色谱柱上进行高效液相色谱分析时，AQ4N 会自发形成这种氧化物。

  DOI：

  10.1039/a905611d

文献信息

• Formulations of anthraquinone derivatives
  申请人：Halbert William Gavin

  公开号：US20070027136A1

  公开（公告）日：2007-02-01

  A stable, sterile aqueous solution of a compound of formula (I): in which A is a C alkylene group with a chain length between NH and N(O)R′R″ of at least 2 carbon atoms and R′ and R″ are each separately selected from C 1-4 alkyl groups and C 2-4 hydroxyalkyl and C 2-4 dihydroxyalkyl groups, or R′ and R″ together are a C 2-6 alkylene group, is formulated in a unit dosage form in a sealed container, said solution having a concentration of the compound of formula (I) up to 150 mg/ml and a pH in the range of 5 to 9. The solution may be prepared without a freeze drying step.
• Process for the preparation of aq4n
  申请人：Matthews Timothy William Ian

  公开号：US20070161808A1

  公开（公告）日：2007-07-12

  A process for the preparation of compound AQ4N of formula (2) or a salt or solvate thereof wherein the said process includes the reaction step: Formula (1), Formula (2), where compound AQ4 of formula (1) is oxidised to compound AQ4N of formula (2) with an oxidising agent at a reaction temperature not exceeding 10° C.
• US7276537B2
  申请人：——

  公开号：US7276537B2

  公开（公告）日：2007-10-02
• A large-scale synthesis of the bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)
  作者：Ho H. Lee、William A. Denny

  DOI：10.1039/a905611d

  日期：——

  A large-scale synthesis of the bis-bioreductive drug 1,4-bis[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N) has been developed. This six-step synthesis provides AQ4N in 20% overall yield from readily available tetrachlorophthalic anhydride. The key step was a KF–NaF-mediated conversion of 3,6-dichlorophthalic anhydride to 3,6-difluorophthalic anhydride, which could be achieved in 77% yield on a 100 g scale. A trace impurity in AQ4N was determined (by LC-MS and independent synthesis) to be the mono-N-oxide 1-amino-4-[2-(dimethylamino)ethyl]amino-5,8-dihydroxyanthracene-9,10-dione N-oxide. This is formed spontaneously from AQ4N under a number of conditions, including during HPLC on reversed-phase columns.

  我们开发了一种大规模合成双生物还原药物 1,4-双[2-（二甲基氨基）乙基]氨基}-5,8-二羟基蒽-9,10-二酮双-N-氧化物（AQ4N）的方法。这种六步合成法能以容易获得的四氯邻苯二甲酸酐为原料合成 AQ4N，总收率为 20%。关键步骤是在 KF-NaF 介导下将 3,6-二氯邻苯二甲酸酐转化为 3,6-二氟邻苯二甲酸酐，在 100 克的规模上产率为 77%。通过 LC-MS 和独立合成）确定 AQ4N 中的痕量杂质为 1-氨基-4-[2-（二甲基氨基）乙基]氨基-5,8-二羟基蒽-9,10-二酮 N-氧化物。在多种条件下，包括在反相色谱柱上进行高效液相色谱分析时，AQ4N 会自发形成这种氧化物。