4-氨基-2-异丙基-5-嘧啶甲腈 | 91055-64-0

• 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: 4-氨基-2-异丙基-5-嘧啶甲腈
• 中文别名: 1,4-二{[5-(二甲氨基)戊基]氨基}蒽-9,10-二酮
• 英文名称: 4-amino-2-isopropyl-pyrimidine-5-carbonitrile
• 英文别名: 4-Amino-2-isopropylpyrimidine-5-carbonitrile；4-amino-2-propan-2-ylpyrimidine-5-carbonitrile
• CAS: 91055-64-0
• 化学式: C₈H₁₀N₄
• 分子量: 162.194
• InChiKey: KCZCPPLAGLQDMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-氨基-2-异丙基-5-嘧啶甲腈 、 丙二腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 5,7-Diamino-2-propan-2-ylpyrido[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Negishi cross-coupling enabled synthesis of novel NAD+-dependent DNA ligase inhibitors and SAR development

  摘要：

  Two novel compounds, pyridopyrimidines (1) and naphthyridines (2) were identified as potent inhibitors of bacterial NAD(+)-dependent DNA ligase (Lig) A in a fragment screening. SAR was guided by molecular modeling and X-ray crystallography. It was observed that the diaminonitrile pharmacophore made a key interaction with the ligase enzyme, specifically residues Glu114, Lys291, and Leu117. Synthetic challenges limited opportunities for diversification of the naphthyridine core, therefore most of the SAR was focused on a pyridopyrimidine scaffold. The initial diversification at R-1 improved both enzyme and cell potency. Further SAR developed at the R-2 position using the Negishi cross-coupling reaction provided several compounds, among these compounds 22g showed good enzyme potency and cellular potency. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.075
• 作为产物：
  描述：

  2-溴-4-氨基-5-氰基嘧啶 、 zinc,propane,bromide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到4-氨基-2-异丙基-5-嘧啶甲腈
  参考文献：
  名称：

  Negishi cross-coupling enabled synthesis of novel NAD+-dependent DNA ligase inhibitors and SAR development

  摘要：

  Two novel compounds, pyridopyrimidines (1) and naphthyridines (2) were identified as potent inhibitors of bacterial NAD(+)-dependent DNA ligase (Lig) A in a fragment screening. SAR was guided by molecular modeling and X-ray crystallography. It was observed that the diaminonitrile pharmacophore made a key interaction with the ligase enzyme, specifically residues Glu114, Lys291, and Leu117. Synthetic challenges limited opportunities for diversification of the naphthyridine core, therefore most of the SAR was focused on a pyridopyrimidine scaffold. The initial diversification at R-1 improved both enzyme and cell potency. Further SAR developed at the R-2 position using the Negishi cross-coupling reaction provided several compounds, among these compounds 22g showed good enzyme potency and cellular potency. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.075

文献信息

• CYCLIC AMINOMETHYL PYRIMIDINE DERIVATIVE
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US20160122319A1

  公开（公告）日：2016-05-05

  The present invention provides a cyclic aminomethyl pyrimidine derivative and a pharmaceutically acceptable salt thereof with high selectivity for dopamine D 4 receptors, which are useful for treating a disease such as attention deficit hyperactivity disorder. Specifically, a compound of formula (1) or a pharmaceutically acceptable salt thereof is provided, wherein n and m are independently 1 or 2; R a is C 1-6 alkyl group, C 3-6 cycloalkyl group, or amino group; R b is hydrogen atom, C 1-6 alkyl group or the like, provided that when R a is amino group, then R b is hydrogen atom; R c1 and R c2 are independently hydrogen atom, or C 1-6 alkyl group; R d1 and R d2 are independently hydrogen atom, fluorine atom or the like; ring Q is an optionally-substituted pyridyl group or an optionally-substituted isoquinolyl group; and the bond having a dashed line is a single or double bond.

  本发明提供了一种对多巴胺D4受体具有高选择性的环状氨基甲基嘧啶衍生物及其药用盐，可用于治疗注意力缺陷多动症等疾病。具体提供了一种公式(1)的化合物或其药用盐，其中n和m独立为1或2；Ra为C1-6烷基、C3-6环烷基或氨基；Rb为氢原子、C1-6烷基等，条件是当Ra为氨基时，Rb为氢原子；Rc1和Rc2独立为氢原子或C1-6烷基；Rd1和Rd2独立为氢原子、氟原子等；环Q为可选取代的吡啶基或可选取代的异喹啉基；且虚线表示的键为单键或双键。
• Nicotinamide Derivatives
  申请人：Blake Tanisha D.

  公开号：US20080146569A1

  公开（公告）日：2008-06-19

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）的化合物及其药用可接受的盐和溶剂化合物，其中取代基如本文所定义，包含这种化合物的组合物以及这种化合物用于治疗各种疾病和状况，如哮喘。
• Heterocyclic compounds useful in treating diseases and conditions
  申请人：Blake Tanisha D.

  公开号：US20080207651A1

  公开（公告）日：2008-08-28

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）化合物及其药学上可接受的盐和溶剂化物，其中取代基如本文所定义，包含此类化合物的组合物以及此类化合物用于治疗各种疾病和病况，如哮喘的用途。
• Heterocyclic Compounds Useful in Treating Diseases and Conditions
  申请人：Blake Tanisha D.

  公开号：US20090281125A1

  公开（公告）日：2009-11-12

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）的化合物及其药学上可接受的盐和溶剂化物，其中取代基的定义如本文所述，包含这种化合物的组合物以及利用这种化合物治疗哮喘等各种疾病和病况的用途。
• ANTI-VIRAL COMPOUNDS
  申请人：Betebenner A. David

  公开号：US20070197558A1

  公开（公告）日：2007-08-23

  Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, co-formulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

  本发明公开了一种有效抑制丙型肝炎病毒（“HCV”）或其他病毒复制的化合物。本发明还涉及包含这些化合物的组合物、这些化合物与其他抗病毒或治疗剂的联合配方或联合给药、合成这些化合物的过程和中间体，以及使用这些化合物治疗HCV或其他病毒感染的方法。