N4-丁基-6-氯-4,5-嘧啶二胺 | 41259-67-0

• 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: N4-丁基-6-氯-4,5-嘧啶二胺
• 中文别名: N4-丁基-6-氯嘧啶-4,5-二胺
• 英文名称: N⁴-butyl-6-chloropyrimidine-4,5-diamine
• 英文别名: 4-n-butylamino-5-amino-6-chloropyrimidine；5-amino-4-chloro-6-(butylamino)pyrimidine；N⁴-butyl-6-chloro-pyrimidine-4,5-diyldiamine；N⁴-Butyl-6-chlor-pyrimidin-4,5-diyldiamin；n4-Butyl-6-chloropyrimidine-4,5-diamine；4-N-butyl-6-chloropyrimidine-4,5-diamine
• CAS: 41259-67-0
• 化学式: C₈H₁₃ClN₄
• mdl: MFCD05858479
• 分子量: 200.671
• InChiKey: BJTOSXADXKQKEW-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: heptane (142-82-5))
• 沸点：
  128 °C(Press: 0.07-0.09 Torr)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N4-丁基-6-氯-4,5-嘧啶二胺 在 氨 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 18.5h， 生成 9-butyl-8-(3,4,5-trimethoxy-benzyl)-9H-purin-6-ylamine
  参考文献：
  名称：

  Adenine derived inhibitors of the molecular chaperone HSP90—SAR explained through multiple X-ray structures

  摘要：

  Multiple co-crystal structures of an adenine-based series of inhibitors bound to the molecular chaperone Hsp90 have been determined. These structures explain the observed SAR for previously described compounds and new compounds, which possess up to 8-fold improved potency against the isolated enzyme. Anti-tumour cell potency and mechanism of action data is also described for the most potent compounds. These data should enable the design of more potent Hsp90 inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.011
• 作为产物：
  描述：

  N-丁基-6-氯-5-硝基-4-嘧啶胺 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以61%的产率得到N4-丁基-6-氯-4,5-嘧啶二胺
  参考文献：
  名称：

  通过5-氨基-4-氯-6-烷基氨基嘧啶与N，N-二甲基链烷酰胺和醇盐离子的反应有效地一锅合成6-烷氧基-8,9-二烷基嘌呤

  摘要：

  许多新的6-烷氧基-8,9-（二取代）嘌呤的合成是通过将相应的中间体5-氨基-4-氯-6-（烷基氨基）嘧啶经醇盐和各种N促进的环化来完成的，N-二甲基酰胺，后者用作溶剂-试剂。通过这种三组分缩合反应，我们能够在嘌呤环的8位引入烷基，同时用烷氧基部分亲核取代6-氯。

  DOI：

  10.1016/s0040-4020(02)00867-0

文献信息

• An efficient one-pot synthesis of 6-alkoxy-8,9-dialkylpurines via reaction of 5-amino-4-chloro-6-alkylaminopyrimidines with N,N-dimethylalkaneamides and alkoxide ions
  作者：Pier Giovanni Baraldi、Asier Unciti Broceta、Maria Josè Pineda de las Infantas、Juan Josè Dı̀az Mochun、Antonio Espinosa、Romeo Romagnoli

  DOI：10.1016/s0040-4020(02)00867-0

  日期：2002.9

  ines has been accomplished by the cyclization of the corresponding intermediate 5-amino-4-chloro-6-(alkylamino)pyrimidines promoted by alkoxides and various N,N-dimethyl amides, where the latter act as solvent–reagents. By this three-component condensation reaction we are able to introduce an alkyl group in the 8 position of the purine ring with the concomitant nucleophilic replacement of the 6-chloro

  许多新的6-烷氧基-8,9-（二取代）嘌呤的合成是通过将相应的中间体5-氨基-4-氯-6-（烷基氨基）嘧啶经醇盐和各种N促进的环化来完成的，N-二甲基酰胺，后者用作溶剂-试剂。通过这种三组分缩合反应，我们能够在嘌呤环的8位引入烷基，同时用烷氧基部分亲核取代6-氯。
• Synthesis of novel tricyclic 4-chloro-7,8,10,11-tetrahydro-5H-benzo[e]pyrimido[4,5-b][1,4]diazepin-9(6H)-ones
  作者：Jinbao Xiang、Lianyou Zheng、Tong Zhu、Qun Dang、Xu Bai

  DOI：10.1002/jhet.384

  日期：——

  A series of tricyclic 7,8,10,11‐tetrahydro‐5H‐benzo[e]pyrimido[4,5‐b][1,4]diazepin‐9(6H)‐ones were prepared in moderate to high yields using TFA‐promoted iminium‐cyclization reactions of 3‐(6‐(butylamino)‐4‐chloropyrimidin‐5‐ylamino)cyclohex‐2‐enones and various aldehydes. J. Heterocyclic Chem., (2010).

  以中等至高收率制备了 一系列三环7,8,10,11-四氢-5 H-苯并[ e ]嘧啶基[4,5- b ] [1,4]二氮杂pin-9（6 H）-酮使用TFA促进的3-（6-（丁基氨基）-4-氯嘧啶-5-氨基氨基）环己基-2-烯酮和各种醛的亚胺环化反应。J.杂环化​​学。（2010）。
• Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
  申请人：Kasibhatla R. Srinivas

  公开号：US20070129334A1

  公开（公告）日：2007-06-07

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same. Methods of using the novel purine compounds of the invention, and tautomers and pharmaceutically acceptable salts thereof, include their use in inhibiting heat shock protein 90's (HSP90's) to thereby treat or prevent HSP90-dependent diseases, e.g., proliferative disorders such as breast cancer.

  本发明描述了新型嘌呤化合物及其互变异构体和药学上可接受的盐，以及包含它们的制药组合物、包含它们的复合物（例如HSP90复合物）和使用它们的方法。使用本发明的新型嘌呤化合物、互变异构体和药学上可接受的盐的方法包括在抑制热休克蛋白90（HSP90）中使用它们，从而治疗或预防HSP90依赖性疾病，例如增生性疾病如乳腺癌。
• 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.
• A study of nitrogen- and oxygen-containing heterocycles. 42. Pyrimido[4,5-b]- and pyrido[2,3-b]-1,4-benzoxazepines
  作者：L. G. Levkovskaya、N. V. Sazonov、N. A. Grineva、I. E. Mamaeva、L. A. Serochkina、T. S. Safonova

  DOI：10.1007/bf00505911

  日期：1985.1

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