6,7-二氯-3,5-二氢-1-羟基咪唑并[1,2-a]喹唑啉-2(1H)-酮 | 875467-41-7

• 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: 6,7-二氯-3,5-二氢-1-羟基咪唑并[1,2-a]喹唑啉-2(1H)-酮
• 英文名称: 6,7-dichloro-1-hydroxy-3,5-dihydro-imidazo[1,2-a]quinazolin-2-one
• 英文别名: 6,7-dichloro-1-hydroxy-3,5-dihydro-1H-imidazo[1,2-a]quinazolin-2-one
• CAS: 875467-41-7
• 化学式: C₁₀H₇Cl₂N₃O₂
• 分子量: 272.09
• InChiKey: SPQQGKKQCRFNPT-UHFFFAOYSA-N

物化性质

• 熔点：
  >169°C (dec.)
• 沸点：
  480.7±55.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微、加热和超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6,7-二氯-3,5-二氢-1-羟基咪唑并[1,2-a]喹唑啉-2(1H)-酮 在 吡啶 作用下， 以47%的产率得到acetic acid 4-acetyl-6,7-dichloro-2-oxo-1,2,4,5-tetrahydroimidazo[1,2-a]quinazolin-1-yl ester
  参考文献：
  名称：

  SYNTHESIS AND STABILITY OF 3-HYDROXYANAGRELIDE, A BIOLOGICALLY POTENT METABOLITE OF ANAGRELIDE

  摘要：

  Metabolism of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (anagrelide), a drug for treating essential thrombocythemia, gives 6,7-dichloro-3-hydroxy-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (3-hydroxyanagrelide) and 2-amino-5,6-dichloro-3,4-dihydroquinazoline. To enable the properties of 3-hydroxyanagrelide to be fully evaluated, the racemic compound has been synthesized. In pH 7.4 aqueous buffer 3-hydroxyanagrelide readily equilibrates with an isomer, 6,7-dichloro-1-hydroxy-3,5-dihydroimidazo[1,2-alpha]-quinazolin-2-one,and is also hydrolyzed to 2-amino-5,6-dichloro-3,4-dihydroquinazoline. 3-Hydroxyanagrelide (half-life 40 hours) was the dominant species at equilibrium and it was concluded that the equilibration and decomposition are sufficiently slow that published assays of 3-hydroxyanagrelide are reliable.

  DOI：

  10.3987/com-12-s(n)115
• 作为产物：
  描述：

  2-氨基-5,6-二氯-3,4-二氢喹唑啉氢溴酸盐 在 sodium periodate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 丙酮 、 mineral oil 为溶剂， 反应 62.5h， 生成 6,7-二氯-3,5-二氢-1-羟基咪唑并[1,2-a]喹唑啉-2(1H)-酮
  参考文献：
  名称：

  SYNTHESIS AND STABILITY OF 3-HYDROXYANAGRELIDE, A BIOLOGICALLY POTENT METABOLITE OF ANAGRELIDE

  摘要：

  Metabolism of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (anagrelide), a drug for treating essential thrombocythemia, gives 6,7-dichloro-3-hydroxy-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (3-hydroxyanagrelide) and 2-amino-5,6-dichloro-3,4-dihydroquinazoline. To enable the properties of 3-hydroxyanagrelide to be fully evaluated, the racemic compound has been synthesized. In pH 7.4 aqueous buffer 3-hydroxyanagrelide readily equilibrates with an isomer, 6,7-dichloro-1-hydroxy-3,5-dihydroimidazo[1,2-alpha]-quinazolin-2-one,and is also hydrolyzed to 2-amino-5,6-dichloro-3,4-dihydroquinazoline. 3-Hydroxyanagrelide (half-life 40 hours) was the dominant species at equilibrium and it was concluded that the equilibration and decomposition are sufficiently slow that published assays of 3-hydroxyanagrelide are reliable.

  DOI：

  10.3987/com-12-s(n)115

文献信息

• Quinazoline derivatives useful for the treatment of peripheral arterial disease and as phosphodiesterase inhibitors
  申请人：Franklin Richard

  公开号：US20060030574A1

  公开（公告）日：2006-02-09

  In accordance with the present invention there is provided a method for the treatment of peripheral arterial diseases in a host comprising administering a therapeutically effective amount of compounds having the formulas (I) through (III) or analogues thereof.

  根据本发明，提供了一种治疗宿主外周动脉疾病的方法，包括向宿主投与式(I)到式(III)或其类似物的治疗有效量的化合物。
• Quinazoline derivatives and their use in the treatment of thrombocythemia
  申请人：Franklin Richard

  公开号：US20060052601A1

  公开（公告）日：2006-03-09

  A method for the treatment of thrombocythemia in a subject comprising administering a therapeutically effective amount of compounds having the formulas (I) through (III) or equilibrating forms thereof.

  一种治疗受试者血小板增多症的方法，包括施用治疗有效量的具有式 (I) 至 (III) 的化合物或其平衡形式。
• [EN] QUINAZOLINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF THROMBOCYTHEMIA<br/>[FR] DERIVES DE QUINAZOLINE, UTILISATION DE CES DERNIERS DANS LE TRAITEMENT DE LA THROMBOCYTHEMIE
  申请人：SHIRE HOLDINGS AG

  公开号：WO2006017822A3

  公开（公告）日：2006-08-24
• QUINAZOLINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF THROMBOCYTHEMIA
  申请人：Shire Holdings AG

  公开号：EP1781296B1

  公开（公告）日：2010-03-10
• US7700608B2
  申请人：——

  公开号：US7700608B2

  公开（公告）日：2010-04-20