6-氯-N-环己基-嘧啶-4,5-二胺 | 5449-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氯-N-环己基-嘧啶-4,5-二胺
• 英文名称: 6-chloro-N⁴-cyclohexyl-pyrimidine-4,5-diamine
• 英文别名: 6-chloro-N4-cyclohexylpyrimidine-4,5-diamine；6-chloro-N⁴-cyclohexyl-pyrimidine-4,5-diamine；6-chloro-N⁴-cyclohexyl-pyrimidine-4,5-diyldiamine；6-Chlor-N⁴-cyclohexyl-pyrimidin-4,5-diyldiamin；5-amino-4-chloro-6-[N-(cyclohexylamino)]-pyrimidine；6-Chloro-N~4~-cyclohexylpyrimidine-4,5-diamine；6-chloro-4-N-cyclohexylpyrimidine-4,5-diamine
• CAS: 5449-10-5
• 化学式: C₁₀H₁₅ClN₄
• mdl: MFCD05819953
• 分子量: 226.709
• InChiKey: AUOMJRAPTGJJQB-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  400.7±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-氯-N-环己基-嘧啶-4,5-二胺 以 异丙醇 为溶剂， 反应 6.0h， 生成 N-(9-cyclohexyl-9H-purin-6-yl)-phenylamine
  参考文献：
  名称：

  通过支架优化提高抑制类似物敏感蛋白激酶的选择性

  摘要：

  通过遗传学和化学方法的结合，可以用小分子抑制任何目的蛋白激酶的能力。遗传学用于修饰单个激酶的活性位点，使其不同于所有天然存在的激酶。接下来，有机合成被用于开发一个小分子，该小分子不与野生型激酶结合，但却是一种工程化激酶的有效抑制剂。这种方法被称为化学遗传学，已被用于产生基于吡唑并嘧啶骨架的高效突变型激酶特异性抑制剂。在这里，我们问是否可以提高所得吡唑并嘧啶的选择性，因为它们以低微摩尔IC 50抑制了几种野生型激酶价值观。我们改善等位基因特异性抑制剂选择性的方法是探索第二种激酶抑制剂支架。设计，合成了一系列6,9-二取代嘌呤，并在体外和体内评估了对几种激酶的抑制活性。与现有的吡唑并嘧啶相比，几种嘌呤被证明是有效的针对类似物敏感激酶的抑制剂，并且表现出更高的选择性。

  DOI：

  10.1016/j.tet.2007.02.089
• 作为产物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 环己胺 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 6-氯-N-环己基-嘧啶-4,5-二胺
  参考文献：
  名称：

  一锅合成高功能嘌呤

  摘要：

  使用适合Vilsmeier型试剂的Traube合成，通过一锅简单，无金属的可扩展方法，可以高产量合成高取代的嘌呤。由5-氨基-4-氯嘧啶，制备新的9-芳基取代的氯嘌呤和用于肽核酸合成的中间体。还报道了允许从5-ami基-6-氨基嘧啶快速合成核糖核苷和7-苄基嘌呤的各种方法，以说明这种多功能工具箱的巨大潜力。该途径在核酸领域中对于直接和快速地获得各种新的8-烷基嘌呤核苷似乎是特别令人感兴趣的。

  DOI：

  10.1021/acs.orglett.7b03209

文献信息

• BICYCLIC NITROGENATED HETEROCYCLIC COMPOUND
  申请人：MITSUBISHI TANABE PHARMA CORPORATION

  公开号：US20190185479A1

  公开（公告）日：2019-06-20

  The present invention provides: a novel use of a specific bicyclic nitrogen-containing heterocyclic compound as a PDE7 inhibitor; a novel bicyclic nitrogen-containing heterocyclic compound having a PDE7 inhibitory effect, a method for producing the compound, a use of the compound, and a pharmaceutical composition containing the PDE7 inhibitor or the compound; and others. More specifically, the present invention provides a PDE7 inhibitor containing the compound represented by the formula (I): [wherein the symbols have the same meanings as those described in the description] or a pharmaceutically acceptable salt thereof as an active ingredient.

  本发明提供了：一种将特定的双环氮杂环化合物用作PDE7抑制剂的新用途；具有PDE7抑制作用的新型双环氮杂环化合物，一种制备该化合物的方法，该化合物的用途，以及含有PDE7抑制剂或该化合物的药物组合物；等等。更具体地，本发明提供了一种包含由下式（I）表示的化合物的PDE7抑制剂： [其中符号的含义与描述中所述的相同]或其药学上可接受的盐作为活性成分。
• 6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents
  作者：James L. Kelley、R. Morris Bullock、Mark P. Krochmal、Ed W. McLean、James A. Linn、Micheal J. Durcan、Barrett R. Cooper

  DOI：10.1021/jm960662s

  日期：1997.9.1

  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.
• 8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
  作者：Catia Lambertucci、Ippolito Antonini、Michela Buccioni、Diego Dal Ben、Dhuldeo D. Kachare、Rosaria Volpini、Karl-Norbert Klotz、Gloria Cristalli

  DOI：10.1016/j.bmc.2009.02.030

  日期：2009.4

  Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radioligand binding assays or functional cyclase experiments in respect to their interaction with all the four adenosine receptor subtypes. Results show that the presence of the bromine atom in 8-position of 9-substituted adenines promotes in general the interaction with the adenosine receptors, in particular at the A(2A) subtype. The present study also demonstrates that adenine derivatives could be a good starting point to obtain selective adenosine A(2B) receptor antagonists. (c) 2009 Elsevier Ltd. All rights reserved.
• US4076711A
  申请人：——

  公开号：US4076711A

  公开（公告）日：1978-02-28
• A One-Pot Synthesis of Highly Functionalized Purines
  作者：Renaud Zelli、Waël Zeinyeh、Romain Haudecoeur、Julien Alliot、Benjamin Boucherle、Isabelle Callebaut、Jean-Luc Décout

  DOI：10.1021/acs.orglett.7b03209

  日期：2017.12.1

  Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine

  使用适合Vilsmeier型试剂的Traube合成，通过一锅简单，无金属的可扩展方法，可以高产量合成高取代的嘌呤。由5-氨基-4-氯嘧啶，制备新的9-芳基取代的氯嘌呤和用于肽核酸合成的中间体。还报道了允许从5-ami基-6-氨基嘧啶快速合成核糖核苷和7-苄基嘌呤的各种方法，以说明这种多功能工具箱的巨大潜力。该途径在核酸领域中对于直接和快速地获得各种新的8-烷基嘌呤核苷似乎是特别令人感兴趣的。