4-[[2-(2-Chloroanilino)-2-oxoethyl]amino]butanoic acid | 1154944-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[[2-(2-Chloroanilino)-2-oxoethyl]amino]butanoic acid
• CAS: 1154944-81-6
• 化学式: C₁₂H₁₅ClN₂O₃
• mdl: MFCD12072146
• 分子量: 270.716
• InChiKey: QZMHJZSPTDSPPL-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  519.6±45.0 °C(predicted)
• 密度：
  1.327±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[[2-(2-Chloroanilino)-2-oxoethyl]amino]butanoic acid 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-(2-aminophenyl)-4-[[2-(2-chloroanilino)-2-oxoethyl]amino]butanamide
  参考文献：
  名称：

  Appraisal of GABA and PABA as linker: Design and synthesis of novel benzamide based histone deacetylase inhibitors

  摘要：

  Histone deacetylase inhibitors have been actively explored as a new generation of chemotherapeutics for cancers, generally known as epigenetic therapeutics. Two novel series of N-(2-amino-phenyl)-4-{[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}-butyramide and N-(2-amino-phenyl)-4-{[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}benzamide were designed and synthesized as novel histone deacetylase inhibitors. The anticancer potential of the compounds were determined in-vitro using MTT assay against HCT-116 and U251 (glioma) cell lines and histone deacetylase inhibitory assay. The synthesized compounds were investigated for anti-tumor activity against Ehrlich ascites carcinoma (EAC) cells in Swiss albino mice. The efforts were also made to ascertain structure-activity relationships among test compounds. The results of the present studying represents appraisal of gamma-aminobutyric acid (GABA) and para-aminobenzoic acid (PABA) as linker moiety for development of newer benzamide based histone deacetylase inhibitor. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.058
• 作为产物：
  描述：

  邻氯苯胺 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-[[2-(2-Chloroanilino)-2-oxoethyl]amino]butanoic acid
  参考文献：
  名称：

  Appraisal of GABA and PABA as linker: Design and synthesis of novel benzamide based histone deacetylase inhibitors

  摘要：

  Histone deacetylase inhibitors have been actively explored as a new generation of chemotherapeutics for cancers, generally known as epigenetic therapeutics. Two novel series of N-(2-amino-phenyl)-4-{[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}-butyramide and N-(2-amino-phenyl)-4-{[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}benzamide were designed and synthesized as novel histone deacetylase inhibitors. The anticancer potential of the compounds were determined in-vitro using MTT assay against HCT-116 and U251 (glioma) cell lines and histone deacetylase inhibitory assay. The synthesized compounds were investigated for anti-tumor activity against Ehrlich ascites carcinoma (EAC) cells in Swiss albino mice. The efforts were also made to ascertain structure-activity relationships among test compounds. The results of the present studying represents appraisal of gamma-aminobutyric acid (GABA) and para-aminobenzoic acid (PABA) as linker moiety for development of newer benzamide based histone deacetylase inhibitor. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.058

文献信息

• Appraisal of GABA and PABA as linker: Design and synthesis of novel benzamide based histone deacetylase inhibitors
  作者：Harish Rajak、Pramod Kumar、Poonam Parmar、Bhupendra Singh Thakur、Ravichandran Veerasamy、Prabodh Chander Sharma、Ajay Kumar Sharma、Arun Kumar Gupta、Jawahar Singh Dangi

  DOI：10.1016/j.ejmech.2012.03.058

  日期：2012.7

  Histone deacetylase inhibitors have been actively explored as a new generation of chemotherapeutics for cancers, generally known as epigenetic therapeutics. Two novel series of N-(2-amino-phenyl)-4-[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}-butyramide and N-(2-amino-phenyl)-4-[(2/3/4-substituted-phenylcarbamoyl)-methyl]-amino}benzamide were designed and synthesized as novel histone deacetylase inhibitors. The anticancer potential of the compounds were determined in-vitro using MTT assay against HCT-116 and U251 (glioma) cell lines and histone deacetylase inhibitory assay. The synthesized compounds were investigated for anti-tumor activity against Ehrlich ascites carcinoma (EAC) cells in Swiss albino mice. The efforts were also made to ascertain structure-activity relationships among test compounds. The results of the present studying represents appraisal of gamma-aminobutyric acid (GABA) and para-aminobenzoic acid (PABA) as linker moiety for development of newer benzamide based histone deacetylase inhibitor. (C) 2012 Elsevier Masson SAS. All rights reserved.