4-(2-chloropyridin-4-yl)-N-(3-methylphenyl)pyrimidin-2-amine | 164658-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-chloropyridin-4-yl)-N-(3-methylphenyl)pyrimidin-2-amine
• CAS: 164658-46-2
• 化学式: C₁₆H₁₃ClN₄
• 分子量: 296.759
• InChiKey: MEKYQSZNPTZUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 4-(2-chloropyridin-4-yl)-N-(3-methylphenyl)pyrimidin-2-amine 反应 0.25h， 生成 N-(3-methylphenyl)-4-(2-morpholin-4-ylpyridin-4-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Identification of pyrimidine derivatives as hSMG-1 inhibitors

  摘要：

  hSMG-1 kinase plays a dual role in a highly conserved RNA surveillance pathway termed nonsense-mediated RNA decay (NMD) and in cellular genotoxic stress response. Since deregulation of cellular responses to stress contributes to tumor growth and resistance to chemotherapy, hSMG-1 is a potential target for cancer treatment. From our screening efforts, we have identified pyrimidine derivatives as hSMG-1 kinase inhibitors. We report structure-based optimization of this pan-kinase scaffold to improve its biochemical profile and overall kinome selectivity, including mTOR and CDK, to generate the first reported selective hSMG-1 tool compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.107
• 作为产物：
  描述：

  3-甲基苯胺 在 硝酸 、 sodium ethanolate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-chloropyridin-4-yl)-N-(3-methylphenyl)pyrimidin-2-amine
  参考文献：
  名称：

  Identification of pyrimidine derivatives as hSMG-1 inhibitors

  摘要：

  hSMG-1 kinase plays a dual role in a highly conserved RNA surveillance pathway termed nonsense-mediated RNA decay (NMD) and in cellular genotoxic stress response. Since deregulation of cellular responses to stress contributes to tumor growth and resistance to chemotherapy, hSMG-1 is a potential target for cancer treatment. From our screening efforts, we have identified pyrimidine derivatives as hSMG-1 kinase inhibitors. We report structure-based optimization of this pan-kinase scaffold to improve its biochemical profile and overall kinome selectivity, including mTOR and CDK, to generate the first reported selective hSMG-1 tool compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.107

文献信息

• PHARMACOLOGICALLY ACTIVE PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：Novartis AG

  公开号：EP0672041B1

  公开（公告）日：2001-11-14
• US5728708A
  申请人：——

  公开号：US5728708A

  公开（公告）日：1998-03-17
• [EN] PHARMACOLOGICALLY ACTIVE PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] DERIVES PYRIDINE PHARMACOLOGIQUEMENT ACTIFS AINSI QUE LEURS PROCEDES DE PREPARATION
  申请人：CIBA-GEIGY AG

  公开号：WO1995009853A1

  公开（公告）日：1995-04-13

  (EN) N-phenyl-2-pyrimidineamine derivatives of formula (I) wherein the substituents are as defined in claim 1 are described. Those compounds can be used, for example, in the treatment of tumour diseases.(FR) L'invention se rapporte à des dérivés de N-phényl-2-pyrimidineamine de formule (I) dans laquelle les substituants sont tels que définis dans la revendication 1. On peut utiliser ces composés, par exemple, dans le traitement des affections tumorales.
• [EN] PYRIDINYLPYRIMIDINE AMINES AS IMMUNOGLOBULINE E (IgE) SYNTHESIS INHIBITORS<br/>[FR] AMINES DE PYRIDINYLPYRIMIDINE AGISSANT COMME INHIBITEURS DE LA SYNTHESE DE L'IMMUNOGLOBULINE E (IgE)
  申请人：NOVARTIS AG

  公开号：WO1999035140A1

  公开（公告）日：1999-07-15

  (EN) Use of the compounds of formula (I) wherein R1 is halogen, phenyl or alkyl and R2 is hydrogen, halogen, alkyl, alkoxy or trifluoromethyl, in free form or salt form, in the treatment of IgE-mediated diseases, including i.a. chronic transplant rejection. The compounds of formula (I) are partly known. A subgroup thereof, namely the compounds of formula (Ib) wherein either R1' is halogen of atomic number 17 or 35 and R2' is hydrogen or alkoxy, or R1' is phenyl or alkyl and R2' is hydrogen, halogen, alkyl, alkoxy or trifluoromethyl, is novel and possesses remarkable cell type specificity. The compounds of formula (Ib) may be prepared e.g. by chlorination or bromination in adjacent position to an N-oxido group or by reaction of the resultant chloro or bromo compound with an organometallic compound.(FR) L'invention concerne, pour le traitement de maladies à médiation IgE, dont le rejet chronique, l'utilisation, sous forme libre ou de sel, de composés représentés par la formule générale (I). Dans cette formule, R1 est halogène, phényle ou alkyle, R2 étant hydrogène, halogène, alkyle, alcoxy ou trifluorométhyle. Les composés représentés par la formule (I) sont en partie connus. L'invention concerne également un sous-groupe de ces derniers, lequel sous-groupe possède une spécificité remarquable par rapport à certains types de cellules. Ce sous-groupe rassemble en l'occurrence ceux des composés qui sont représentés par la formule (Ib). Dans cette formule, soit R1' est halogène avec un numéro atomique de 17 à 35 et R2' est hydrogène ou alcoxy, soit R1' est phényle ou alkyle et R2' est hydrogène, halogène, alkyle, alcoxy ou trifluorométhyle. Les composés représentés par la formule (Ib) peuvent être préparés, par exemple par chloration ou bromation au niveau d'une position adjacente à un groupe N-oxydo ou par mise en réaction du composé chloro ou bromo avec un composé organométallique.
• Identification of pyrimidine derivatives as hSMG-1 inhibitors
  作者：Ariamala Gopalsamy、Eric M. Bennett、Mengxiao Shi、Wei-Guo Zhang、Joel Bard、Ker Yu

  DOI：10.1016/j.bmcl.2012.08.107

  日期：2012.11

  hSMG-1 kinase plays a dual role in a highly conserved RNA surveillance pathway termed nonsense-mediated RNA decay (NMD) and in cellular genotoxic stress response. Since deregulation of cellular responses to stress contributes to tumor growth and resistance to chemotherapy, hSMG-1 is a potential target for cancer treatment. From our screening efforts, we have identified pyrimidine derivatives as hSMG-1 kinase inhibitors. We report structure-based optimization of this pan-kinase scaffold to improve its biochemical profile and overall kinome selectivity, including mTOR and CDK, to generate the first reported selective hSMG-1 tool compound. (C) 2012 Elsevier Ltd. All rights reserved.