4-胍基甲基苯甲酸甲酯 | 736080-30-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-胍基甲基苯甲酸甲酯
• 英文名称: 4-guanidinomethylbenzoic acid methyl ester
• 英文别名: methyl 4-(guanidinomethyl)benzoate；4-guanidinomethyl-benzoic acid methyl ester dihydrate；4-Guanidinomethyl-benzoic acid methyl ester；methyl (4-guanidinomethyl) benzoate；4-Guanidinomethylbenzoesaeuremethylester；methyl 4-[(diaminomethylideneamino)methyl]benzoate
• CAS: 736080-30-1
• 化学式: C₁₀H₁₃N₃O₂
• mdl: MFCD23136031
• 分子量: 207.232
• InChiKey: RUSQUIYMDUXKSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-胍基甲基苯甲酸甲酯 在 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 68.0h， 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：

  4-氨甲基苯甲酸甲酯盐酸盐 、 1H-吡唑-1-甲脒盐酸盐 在 碳酸氢钠 、 水 、 乙醚 作用下， 以 N,N-二甲基甲酰胺 、 N,N-二异丙基乙胺 为溶剂， 反应 4.17h， 以to give 12.32 g white crystallin a solid intermediate 1 (77% yield, M+1: 208 on MS)的产率得到4-胍基甲基苯甲酸甲酯
  参考文献：
  名称：

  Inhibitors of histone deacetylase

  摘要：

  本发明涉及到组蛋白去乙酰化酶的抑制。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。本发明还提供了治疗细胞增殖性疾病和病症的组合物和方法。

  公开号：

  US07868204B2

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。
• [EN] PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRIMIDINES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PYRIMIDINES SUBSTITUÉES
  申请人：METHYLGENE INC

  公开号：WO2015006875A1

  公开（公告）日：2015-01-22

  This invention relates to an improved process of making compounds of Formula (I) and synthetic intermediates thereof. (I) In particular, the invention relates to an improved process to prepare N-(2-aminophenyl)-4- ((pyrimidin-2-ylamino)methyl)benzamides which requires fewer steps, is efficient, can be used on an industrial scale, and results in a final product which is suitable for pharmaceutical use.

  这项发明涉及一种改进的制备化合物(I)及其合成中间体的方法。具体而言，该发明涉及一种改进的方法，用于制备N-(2-氨基苯基)-4-((嘧啶-2-基氨基)甲基)苯甲酰胺，该方法需要较少的步骤，高效，可用于工业规模，并得到适用于药物使用的最终产品。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE
  申请人：METHYLGENE INC

  公开号：WO2005092899A1

  公开（公告）日：2005-10-06

  The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.

  这项发明涉及一系列对抑制组蛋白去乙酰化酶（HDAC）酶活性有用的化合物。该发明还提供了一种利用这些化合物抑制细胞中组蛋白去乙酰化酶的方法，以及一种利用这些HDAC抑制剂治疗细胞增殖性疾病和病况的方法。此外，该发明提供了包含这些HDAC抑制化合物和药用可接受载体的药物组合物。
• [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：Delorme Daniel

  公开号：US20070213330A1

  公开（公告）日：2007-09-13

  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技术。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。本发明还提供了治疗细胞增殖性疾病和病况的组合物和方法。