2,6-二吡咯烷-1-基嘧啶-4-胺 | 331268-12-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,6-二吡咯烷-1-基嘧啶-4-胺
• 英文名称: 2,6-Di(pyrrolidin-1-yl)pyrimidin-4-amine
• 英文别名: 2,6-dipyrrolidin-1-ylpyrimidin-4-amine
• CAS: 331268-12-3
• 化学式: C₁₂H₁₉N₅
• 分子量: 233.316
• InChiKey: DWVDKFKHTJFPSH-UHFFFAOYSA-N

物化性质

• 沸点：
  488.5±55.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对苯醌 、 2,6-二吡咯烷-1-基嘧啶-4-胺 在 溶剂黄146 作用下， 反应 6.0h， 以55%的产率得到2,4-Di-pyrrolidin-1-yl-9H-pyrimido[4,5-b]indol-6-ol
  参考文献：
  名称：

  通过扩展 Nenitzescu 反应合成具有药用意义的 2,4-Diamino-9H-pyrimido[4,5-b]indol-6-ols

  摘要：

  标题化合物 6 通过一步法从 1,4-苯醌 (1) 和嘧啶-2,4,6-三胺 2 经由 Nenitzescu 反应的延伸制备。9H-嘧啶并[4,5-b]吲哚6的形成可以通过嘧啶-2,4,6-三胺2的C-5的1 3 C NMR值计算。

  DOI：

  10.1055/s-2004-822887
• 作为产物：
  描述：

  四氢吡咯 、 4-氨基-2,6-二氯嘧啶 反应 18.0h， 以52%的产率得到2,6-二吡咯烷-1-基嘧啶-4-胺
  参考文献：
  名称：

  Synthesis of 2,4-Di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indoles, Including Antiasthma Clinical Candidate PNU-142731A

  摘要：

  Two syntheses are described for 1-[(2,4.di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indol-9-yl)-acetyl]pyrrolidine hydrochloride (PNU-142731A), a clinical candidate in the asthma area. The route involving the initial regioselective addition of glycine ethyl ester to commercially available 2,4,6-trichloropyrimidine is particularly well suited for large-scale operation, as it is short, proceeds in good yield, is operationally straightforward, and requires no chromatographic purification of intermediates.

  DOI：

  10.1021/op000221p

文献信息

• Synthesis of Medicinally Interesting 2,4-Diamino-9<i>H</i>-pyrimido[4,5-<i>b</i>]indol-6-ols via Extension of the Nenitzescu Reaction
  作者：Reinhard Troschütz、Bernd Dotzauer

  DOI：10.1055/s-2004-822887

  日期：——

  The title compounds 6 were prepared by a one-step procedure from 1,4-benzoquinone (1) and pyrimidine-2,4,6-triamines 2 via an extension of the Nenitzescu reaction. Formation of 9H-pyrimido[4,5-b]indoles 6 can be calculated by 1 3 C NMR values of C-5 of the pyrimidine-2,4,6-triamines 2.

  标题化合物 6 通过一步法从 1,4-苯醌 (1) 和嘧啶-2,4,6-三胺 2 经由 Nenitzescu 反应的延伸制备。9H-嘧啶并[4,5-b]吲哚6的形成可以通过嘧啶-2,4,6-三胺2的C-5的1 3 C NMR值计算。
• [EN] PEPTIDOMIMETIC GALANIN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS À LA GALANINE PEPTIDOMIMÉTIQUES
  申请人：ROBERTS EDWARD

  公开号：WO2012009258A2

  公开（公告）日：2012-01-19

  Potent and effective modulators of galanin receptors such as Ga1R1 and Ga1R2 are provided. Methods of preparation and methods of use are further provided. The compounds of the invention may be effective for treatment of malconditions in human patients including epilepsy or seizure disorders, mood disorders including depression and anxiety spectrum disorders; drug addiction including addiction to alcohol or tobacco; autistic spectrum diseases and pervasive development disorders; Alzheimer's disease or other dementias; cognition disorders; cerebral or myocardial stroke; demyelinating diseases including multiple sclerosis, Guillain-Barre syndrome and Charcot-Marie-Tooth disease; neurodegenerative diseases including Parkinson's disease, Lou Gehrig's diseases, Huntington's disease, and HIV dementia; neurotrauma; diabetes, obesity, metabolic syndrome and feeding disorders; solid tumors and leukemia/lymphoma; pain; neuropathies; sleeping disorders and regulation; neuroprotection; and inflammation.
• Synthesis of 2,4-Di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indoles, Including Antiasthma Clinical Candidate PNU-142731A
  作者：Gordon L. Bundy、Lee S. Banitt、Paul J. Dobrowolski、John R. Palmer、Theresa M. Schwartz、David C. Zimmermann、Michael F. Lipton、Michael A. Mauragis、Michael F. Veley、Robert B. Appell、Robert C. Clouse、Edward D. Daugs

  DOI：10.1021/op000221p

  日期：2001.3.1

  Two syntheses are described for 1-[(2,4.di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indol-9-yl)-acetyl]pyrrolidine hydrochloride (PNU-142731A), a clinical candidate in the asthma area. The route involving the initial regioselective addition of glycine ethyl ester to commercially available 2,4,6-trichloropyrimidine is particularly well suited for large-scale operation, as it is short, proceeds in good yield, is operationally straightforward, and requires no chromatographic purification of intermediates.
• 2,4-Diamino-9H-pyrimido[4,5-b]indol-5-ols: Synthesis, in vitro cytotoxic activity, and QSAR investigations
  作者：Bernd Dotzauer、Renate Grünert、Patrick J. Bednarski、Harald Lanig、Jens Landwehr、Reinhard Troschütz

  DOI：10.1016/j.bmc.2006.06.051

  日期：2006.11

  A series of novel 2,4-diaminopyrimido[4,5-b]indol-6-ols has been synthesized and the in vitro cytotoxic activities were evaluated against four human cancer cell lines originating from solid tumors. An increase in activity was observed when a heteroaromatic ring was annulated on side g of the pyrimido[4,5-b]indole system to give compounds with activities comparable to ellipticine and cisplatin. To understand

  合成了一系列新颖的2,4-二氨基嘧啶[4,5-b]吲哚6-醇，并针对四种源自实体瘤的人类癌细胞系评估了体外细胞毒活性。当在嘧啶并[4，5-b]吲哚系统的g侧上环杂芳环时，观察到活性增加，从而得到具有与玫瑰树碱和顺铂相当的活性的化合物。为了了解实验性细胞毒性活性，进行了QSAR研究，结果表明实验性IC和预测IC之间具有很好的线性关系（50）。