4-amino-2-phenyl-6-(2,4-dichlorophenyl)-pyrimidine-5-carbonitrile | 475995-40-5

• 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: 4-amino-2-phenyl-6-(2,4-dichlorophenyl)-pyrimidine-5-carbonitrile
• 英文别名: 4-amino-6-(2,4-dichlorophenyl)-2-phenylpyrimidine-5-carbonitrile；4-Amino-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidine-5-carbonitrile
• CAS: 475995-40-5
• 化学式: C₁₇H₁₀Cl₂N₄
• 分子量: 341.199
• InChiKey: BKLTZUCRTFNTFM-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-2-phenyl-6-(2,4-dichlorophenyl)-pyrimidine-5-carbonitrile 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 5-Aminomethyl-6-(2,4-dichloro-phenyl)-2-phenyl-pyrimidin-4-ylamine
  参考文献：
  名称：

  Pyridine and pyrimidine derivatives

  摘要：

  本发明提供了化合物的公式（I）1，其中R1、R2、R3、R4和X如规范中所定义，以及其药用盐。这些化合物可用于治疗和/或预防与DPP IV相关的疾病，如糖尿病，特别是非胰岛素依赖型糖尿病和糖耐量受损。

  公开号：

  US20030216382A1
• 作为产物：
  描述：

  2,4-二氯苯甲醛 以 甲醇 为溶剂， 反应 11.0h， 生成 4-amino-2-phenyl-6-(2,4-dichlorophenyl)-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  De Melo, Sebastiao Jose; Dos Santos, Leila Cabral; Da S. Falcao, Emerson Peter, Journal of Chemical Research - Part S, 2002, # 5, p. 216 - 217

  摘要：

  DOI：

文献信息

• A Facile Synthesis of New Pyrazolo[3,4-<i>d</i>]pyrimidine Derivatives<i>via</i>a One-Pot Four-Component Reaction with Sodium Acetate Supported on Basic Alumina as Promoter
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan、Reza Aryan、Elyass Isapoor

  DOI：10.1002/hlca.201300060

  日期：2013.12

  efficient one‐pot procedure for the synthesis of 3‐amino‐6‐aryl‐2‐phenylpyrazolo[3,4‐d]pyrimidine derivatives, through the reaction of aldehydes, malononitrile, benzamidine hydrochloride, and hydrazine hydrate in the presence of basic alumina‐supported sodium acetate (AcONa/Al2O3) under reflux conditions, is reported. This protocol has some advantages, including the use of a simple and one‐pot synthetic

  在碱性条件下，通过醛，丙二腈，苯甲hydro盐酸盐和水合肼的反应，可以有效地合成3-氨基-6-芳基-2-苯基吡唑并[3,4- d ]嘧啶衍生物的一锅法据报道，在回流条件下氧化铝负载的乙酸钠（AcONa / Al 2 O 3）。该方案具有一些优点，包括使用简单的单锅合成方法直接从四种容易获得的起始原料中获得吡唑并[3,4- d ]嘧啶，简单的后处理，产品的高总收率以及同时进行NO 2转化为氨基，提供了合成更复杂结构的机会。
• A novel and efficient synthesis of pyrazolo[3,4-d]pyrimidine derivatives and the study of their anti-bacterial activity
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan、Reza Aryan、Hamid Sadeghian、Mahdieh Davoodnejad

  DOI：10.1016/j.cclet.2013.04.035

  日期：2013.7

  4-amino-6-aryl-2-phenyl pyrimidine-5-carbonitrile derivatives were synthesized through a one-pot, three-component reaction of an aldehyde, malononitrile and benzamidine hydrochloride, in the presence of magnetic nano Fe3O4 particles as a catalyst under solvent-free conditions. 3-Amino-6-aryl-2-phenylpyrazolo[3,4-d]pyrimidine derivatives were prepared through an efficient and environmentally friendly reaction between

  在这项工作中，在磁性纳米Fe 3 O的存在下，通过醛，丙二腈和苯甲idine盐酸盐的一锅三组分反应，合成了4-氨基-6-芳基-2-苯基嘧啶-5-甲腈衍生物。在无溶剂条件下有4个颗粒作为催化剂。3-氨基-6-芳基-2-苯基吡唑并[3,4- d ]嘧啶衍生物是通过4-氨基-6-芳基-2-苯基嘧啶-5-甲腈衍生物与水合肼和已对其抗菌活性进行了评估。
• An aminomethylpyrimidine DPP-IV inhibitor with improved properties
  作者：Jens-Uwe Peters、Daniel Hunziker、Holger Fischer、Manfred Kansy、Silja Weber、Stéphane Kritter、Aranka Müller、Angelina Wallier、Fabienne Ricklin、Markus Boehringer、Sonia Maria Poli、Miklos Csato、Bernd-Michael Loeffler

  DOI：10.1016/j.bmcl.2004.04.048

  日期：2004.7

  A recently identified DPP-IV inhibitor (1) was found to induce phospholipidosis and to inhibit CYP3A4. A small series of less lipophilic and less amphiphilic analogues was synthesized in an effort to overcome these issues. One compound from this series was equipotent to 1, did not induce phospholipidosis and showed a reduced CYP3A4 inhibition. (C) 2004 Elsevier Ltd. All rights reserved.
• Aminomethylpyrimidines as novel DPP-IV inhibitors: A 105-fold activity increase by optimization of aromatic substituents
  作者：Jens-Uwe Peters、Silja Weber、Stéphane Kritter、Peter Weiss、Angelina Wallier、Markus Boehringer、Michael Hennig、Bernd Kuhn、Bernd-Michael Loeffler

  DOI：10.1016/j.bmcl.2004.01.019

  日期：2004.3

  The influence of aromatic substitution on a newly discovered class of inhibitors of dipeptidyl peptidase IV was investigated. A 10(5)-fold increase in potency was achieved by the optimization of aromatic substituents in a parallel chemistry program. The observed SAR could be explained by an X-ray structure of the protein-ligand complex.
• NOVEL PYRIDIN- AND PYRIMIDIN-DERIVATIVES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1476435A1

  公开（公告）日：2004-11-17