4-amino-2-benzyl-pyrimidine-5-carbonitrile | 872826-79-4

• 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-benzyl-pyrimidine-5-carbonitrile
• 英文别名: 4-Amino-2-benzyl-pyrimidin-5-carbonitril；4-Amino-2-(phenylmethyl)-5-pyrimidinecarbonitrile；4-amino-2-benzylpyrimidine-5-carbonitrile
• CAS: 872826-79-4
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: FEBPTSNKQKVXMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-benzyl-pyrimidine-5-carbonitrile 在 盐酸 、 水 作用下， 生成 5-aminomethyl-2-benzyl-pyrimidin-4-ylamine
  参考文献：
  名称：

  Matsukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 417,443;dtsch.Ref.S.122,125

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙脒 、 乙氧基亚甲基丙二腈 生成 4-amino-2-benzyl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  DE671787

  摘要：

  公开号：

文献信息

• Negishi cross-coupling enabled synthesis of novel NAD+-dependent DNA ligase inhibitors and SAR development
  作者：Kerry E. Murphy-Benenato、Lakshmaiah Gingipalli、P. Ann Boriack-Sjodin、Gabriel Martinez-Botella、Dan Carcanague、Charles J. Eyermann、Madhu Gowravaram、Jenna Harang、Michael R. Hale、Georgine Ioannidis、Harris Jahic、Michele Johnstone、Amy Kutschke、Valerie A. Laganas、James T. Loch、Matthew D. Miller、Herbert Oguto、Sahil Joe Patel

  DOI：10.1016/j.bmcl.2015.09.075

  日期：2015.11

  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.
• DE667990
  申请人：——

  公开号：——

  公开（公告）日：——
• Process of preparing derivatives of pyrimidine
  申请人：MERCK & CO INC

  公开号：US02235638A1

  公开（公告）日：1941-03-18
• Ohta, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1947, vol. 67, p. 161,164
  作者：Ohta

  DOI：——

  日期：——
• Matsukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 417,443;dtsch.Ref.S.122,125
  作者：Matsukawa

  DOI：——

  日期：——