4-[[[4-(3-吡啶基)-2-嘧啶基]氨基]甲基]苯甲酸甲酯 | 849235-67-2

• 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-[[[4-(3-吡啶基)-2-嘧啶基]氨基]甲基]苯甲酸甲酯
• 英文名称: methyl 4-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)benzoate
• 英文别名: Methyl 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoate；methyl 4-[[(4-pyridin-3-ylpyrimidin-2-yl)amino]methyl]benzoate
• CAS: 849235-67-2
• 化学式: C₁₈H₁₆N₄O₂
• 分子量: 320.351
• InChiKey: DLQTWNZHCZSRAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-[[[4-(3-吡啶基)-2-嘧啶基]氨基]甲基]苯甲酸甲酯 在 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 过氧化物酶（辣根）
  参考文献：
  名称：

  Discovery of Potent, Isoform-Selective Inhibitors of Histone Deacetylase Containing Chiral Heterocyclic Capping Groups and a N-(2-Aminophenyl)benzamide Binding Unit

  摘要：

  The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzmide 24a gave respective IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)benzamides previously reported, an example of each ring system at 1 mu M causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by 24a was observed, with respective IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.

  DOI：

  10.1021/jm400634n
• 作为产物：
  描述：

  1-(3-吡啶基)-3-(二甲氨基)-2-丙烯-1-酮 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 6.25h， 生成 4-[[[4-(3-吡啶基)-2-嘧啶基]氨基]甲基]苯甲酸甲酯
  参考文献：
  名称：

  Navigating into the chemical space between MGCD0103 and SAHA: novel histone deacetylase inhibitors as a promising lead

  摘要：

  使用两种新型组蛋白去乙酰化酶抑制剂在MGCD0103和SAHA之间的化学空间中导航。

  DOI：

  10.1039/c5md00247h

文献信息

• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• Inhibitors of histone deacetylase
  申请人：MethylGene, Inc.

  公开号：US20040142953A1

  公开（公告）日：2004-07-22

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了用于治疗细胞增殖性疾病和病况的组合物和方法。
• Synthesis, Biological Activities and Docking Studies of Novel 4-(Arylaminomethyl)benzamide Derivatives as Potential Tyrosine Kinase Inhibitors
  作者：Elena Kalinichenko、Aliaksandr Faryna、Viktoria Kondrateva、Alena Vlasova、Valentina Shevchenko、Alla Melnik、Olga Avdoshko、Alla Belko

  DOI：10.3390/molecules24193543

  日期：——

  number of new compounds containing the 4-(aminomethyl)benzamide fragment as a linker were designed and synthesized, and their biological activities were evaluated as potential anticancer agents. The cytotoxicity activity of the designed compounds was studied in two hematological and five solid cell lines in comparison with the reference drugs. Targeted structures against eight receptor tyrosine kinases

  设计并合成了许多含有4-(氨基甲基)苯甲酰胺片段作为接头的新化合物，并评估了它们的生物活性作为潜在的抗癌剂。与参考药物相比，在两种血液学和五种固体细胞系中研究了设计化合物的细胞毒性活性。研究了针对八种受体酪氨酸激酶的靶向结构，包括 EGFR、HER-2、HER-4、IGF1R、InsR、KDR、PDGFRa 和 PDGFRb。大多数化合物对测试的激酶显示出有效的抑制活性。在分子的酰胺或胺部分中具有（三氟甲基）苯环的类似物 11 和 13 被证明对 EGFR 具有高度效力，在 10 nM 时分别具有 91% 和 92% 的抑制作用。对蛋白质数据库 (PDB) 数据库中包含的九种蛋白激酶的合成目标化合物进行对接。类似物 10 的分子建模结果表明，使用 4-（氨基甲基）苯甲酰胺作为灵活的接头导致分子的整体几何形状有利，这允许绕过大量异亮氨酸残基并提供与活性分子的必要结合。 T315I 突变体 Abl
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS DE L'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2004069823A1

  公开（公告）日：2004-08-19

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  该发明涉及抑制组蛋白去乙酰化酶的技术。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和病症的组合物和方法。
• Inhibitors of Histone Deacetylase
  申请人：Moradei Oscar

  公开号：US20080132459A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的方法。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和病状的组合物和方法。