4-chloro-N-(4-methoxybenzyl)pyrimidin-2-amine | 115581-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-chloro-N-(4-methoxybenzyl)pyrimidin-2-amine
• 英文别名: 4-chloro-N-(4-methoxybenzyl)-2-pyrimidinamine；4-chloro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine
• CAS: 115581-30-1
• 化学式: C₁₂H₁₂ClN₃O
• 分子量: 249.7
• InChiKey: YUYSFLXALHXZIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(4-methoxybenzyl)pyrimidin-2-amine 在 potassium carbonate 、 肼 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 Ethyl 1-[2-(4-Methoxybenzylamino)-4-pyrimidinyl]-5-methyl-4-pyrazolecarboxylate
  参考文献：
  名称：

  Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity

  摘要：

  Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00568-1
• 作为产物：
  描述：

  2-(4-Methoxy-benzylamino)-pyrimidin-4-ol 在 三氯氧磷 作用下， 反应 2.0h， 生成 4-chloro-N-(4-methoxybenzyl)pyrimidin-2-amine
  参考文献：
  名称：

  Synthesis and mechanism of action of novel pyrimidinyl pyrazole derivatives possessing antiproliferative activity

  摘要：

  Pyrimidinyl pyrazole derivatives 1-4, prepared as a new scaffold of an anti-tumor agent, showed antiproliferative activity against human lung cancer cell lines and inhibited tubulin polymerization. Furthermore, it was found that compound 2 bound at the colchicine site on tubulin, but the tubulin binding pattern was different from that of colchicine. Here, we describe the synthesis of the derivatives and the differences of the action mechanism on tubulin polymerization inhibition between compound 2 and colchicine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00568-1

文献信息

• MONOCYCLIC HETEROCYCLES AS KINASE INHIBITORS
  申请人：Borzilleri Robert M.

  公开号：US20090054436A1

  公开（公告）日：2009-02-26

  The present invention is directed to compounds having the formula and methods for using them for the treatment of cancer.

  本发明涉及具有以下结构式的化合物及其用于癌症治疗的方法。
• Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: Development of chemical probe ML315
  作者：Thomas C. Coombs、Cordelle Tanega、Min Shen、Jenna L. Wang、Douglas S. Auld、Samuel W. Gerritz、Frank J. Schoenen、Craig J. Thomas、Jeffrey Aubé

  DOI：10.1016/j.bmcl.2013.02.096

  日期：2013.6

  Substituted pyrimidine inhibitors of the Clk and Dyrk kinases have been developed, exploring structure-activity relationships around four different chemotypes. The most potent compounds have low-nanomolar inhibitory activity against Clk1, Clk2, Clk4, Dyrk1A and Dyrk1B. Kinome scans with 442 kinases using agents representing three of the chemotypes show these inhibitors to be highly selective for the Clk and Dyrk families. Further off-target pharmacological evaluation with ML315, the most selective agent, supports this conclusion. (C) 2013 Elsevier Ltd. All rights reserved.
• Maggiali; Morini; Mossini, Farmaco, Edizione Scientifica, 1988, vol. 43, # 3, p. 277 - 291
  作者：Maggiali、Morini、Mossini、Morini、Barocelli、Impicciatore

  DOI：——

  日期：——
• US7459562B2
  申请人：——

  公开号：US7459562B2

  公开（公告）日：2008-12-02
• US7714138B2
  申请人：——

  公开号：US7714138B2

  公开（公告）日：2010-05-11