5-amino-6-chloro-4-cyclopropylaminopyrimidine | 195252-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-6-chloro-4-cyclopropylaminopyrimidine
• 英文别名: 5-amino-4-chloro-6-(N-cyclopropylamino)pyrimidine；6-chloro-N-cyclopropylpyrimidine-4,5-diamine；6-chloro-N4-cyclopropylpyrimidine-4,5-diamine；6-chloro-4-N-cyclopropylpyrimidine-4,5-diamine
• CAS: 195252-62-1
• 化学式: C₇H₉ClN₄
• mdl: MFCD09743305
• 分子量: 184.628
• InChiKey: UOZWNOIHCDKJPY-UHFFFAOYSA-N

物化性质

• 沸点：
  368.3±42.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-6-chloro-4-cyclopropylaminopyrimidine 在 乙基磺酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 61.0h， 生成 N,9-二环丙基嘌呤-6-胺
  参考文献：
  名称：

  6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents

  摘要：

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.

  DOI：

  10.1021/jm960662s
• 作为产物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 环丙胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 生成 5-amino-6-chloro-4-cyclopropylaminopyrimidine
  参考文献：
  名称：

  嘌呤类似物的有效合成：FeCl 3 -SiO 2促进4,5-二氨基嘧啶与醛的环化反应，生成6,8,9-三取代嘌呤

  摘要：

  通过6-氯-4,5-二氨基嘧啶和FeCl 3 -SiO 2促进的各种醛的环化，可有效合成6,8,9-三取代嘌呤类似物。硅胶上的氯化亚铁（Fe（III））具有脱水剂和氧化剂的双重作用，并且在后处理过程中可以通过过滤方便地除去。

  DOI：

  10.1016/s0040-4039(00)01074-1

文献信息

• [EN] INHIBITORS OF PI3K-DELTA AND METHODS OF THEIR USE AND MANUFACTURE<br/>[FR] INHIBITEUR DE PI3K-DELTA ET PROCÉDÉS D'UTILISATION ET DE FABRICATION CORRESPONDANTS
  申请人：EXELIXIS INC

  公开号：WO2012037226A1

  公开（公告）日：2012-03-22

  The invention is directed to Compounds of Formula I: and pharmaceutically acceptable salts or solvates thereof, as well as methods of making and using the compounds.

  这项发明涉及到式I的化合物及其药用可接受的盐或溶剂合物，以及制备和使用这些化合物的方法。
• Fructose-1,6-bisphosphatase Inhibitors. 1. Purine Phosphonic Acids as Novel AMP Mimics
  作者：Qun Dang、Brian S. Brown、Yan Liu、Robert M. Rydzewski、Edward D. Robinson、Paul D. van Poelje、M. Rami Reddy、Mark D. Erion

  DOI：10.1021/jm900078f

  日期：2009.5.14

  Inhibition of FBPase is considered a promising way to reduce hepatic gluconeogenesis and therefore could be a potential approach to treat type 2 diabetes. Herein we report the discovery of a series of purine phosphonic acids as AMP mimics targeting the AMP site of FBPase, which was achieved using a structure-guided drug design approach. These non-nucleotide purine analogues inhibit FBPase in a similar

  抑制FBPase被认为是减少肝脏糖异生的有前途的方法，因此可能是治疗2型糖尿病的潜在方法。本文中，我们报道了一系列嘌呤膦酸的发现，它们是针对FBPase AMP位点的AMP模拟物，这是使用结构指导药物设计方法实现的。这些非核苷酸嘌呤类似物以与AMP相似的方式和相似的效力抑制FBPase。更重要的是，几种嘌呤类似物表现出有效的细胞和体内降糖活性，从而获得了抑制FBPase作为药物发现靶标的概念证明。例如，就FBPase抑制而言，化合物4.11和4.13与AMP等价。此外，化合物4.11 抑制原代大鼠肝细胞中的葡萄糖生成，并显着降低禁食大鼠的血糖水平。
• AMINOPYRIMIDINAMIDES AS PESTICIDES
  申请人：MAECHLING Simon

  公开号：US20100298267A1

  公开（公告）日：2010-11-25

  The present application relates to novel aminopyrimidinamides, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本申请涉及新型氨基嘧啶酰胺，其制备方法以及它们用于控制动物害虫，特别是节肢动物，特别是昆虫的用途。
• Efficient synthesis of purine analogues: an FeCl3–SiO2-promoted cyclization reaction of 4,5-diaminopyrimidines with aldehydes leading to 6,8,9-trisubstituted purines
  作者：Qun Dang、Brian S Brown、Mark D Erion

  DOI：10.1016/s0040-4039(00)01074-1

  日期：2000.8

  6,8,9-Trisubstituted purine analogues were efficiently synthesized via cyclization of 6-chloro-4,5-diaminopyrimidines and various aldehydes promoted by FeCl3–SiO2. Fe(III) chloride on silica gel has a dual role of a dehydration agent and an oxidant, and was conveniently removed during work-up by filtration.

  通过6-氯-4,5-二氨基嘧啶和FeCl 3 -SiO 2促进的各种醛的环化，可有效合成6,8,9-三取代嘌呤类似物。硅胶上的氯化亚铁（Fe（III））具有脱水剂和氧化剂的双重作用，并且在后处理过程中可以通过过滤方便地除去。
• Aminopyrimidinamides As Pest Control Agents
  申请人：Maechling Simon

  公开号：US20120071496A1

  公开（公告）日：2012-03-22

  The present application relates to novel aminopyrimidinamides, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.

  本申请涉及新的氨基嘧啶酰胺，其制备过程以及它们用于控制动物害虫，特别是节肢动物，尤其是昆虫的用途。