4-((2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)amino)butanoic acid | 123941-02-6

• 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-((2,6-Dimethylphenyl)amino)-2-oxoethyl)amino)butanoic acid
• 英文别名: 4-[[2-(2,6-dimethylanilino)-2-oxoethyl]amino]butanoic acid
• CAS: 123941-02-6
• 化学式: C₁₄H₂₀N₂O₃
• mdl: MFCD01751643
• 分子量: 264.324
• InChiKey: NAAZEZUKLGBHJF-UHFFFAOYSA-N

物化性质

• 沸点：
  407.55°C (rough estimate)
• 密度：
  1.1032 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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：

  二正丁胺 、 4-((2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)amino)butanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到N,N-dibutyl-4-[[2-(2,6-dimethylanilino)-2-oxoethyl]amino]butanamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of 4-(2-(2,6-dimethylphenylamino)-2-oxoethylamino)-N-(substituted)butanamides: A pharmacophoric hybrid approach

  摘要：

  A series of pharmacoplioric hybrids of ameltolide-gamma-aminobutyric acid (GABA)-amides was designed, synthesized, and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonVUlsant screening was performed using intraperitoneal (ip) maximal electrosbock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ), and subcutaneous picrotoxin (scPIC)induced seizure threshold tests. All the compounds had improved lipophilicity and the pharmacological activity profile confirmed their blood-brain barrier penetration. The titled compounds showed promising activity in scPIC screen indicating the involvement of GABA-mediation. Compound 4-(2-(2,6-dimetbylaminophenylamino)-2-oxoethylamino)-N-(2,6-dimethylphenyl) butanamide (7) emerged as the most potent derivative effective in all the three animal models of seizure with no neurotoxicity at the anticonvulsant dose. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.04.032
• 作为产物：
  描述：

  2,6-二甲基苯胺 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.01h， 生成 4-((2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)amino)butanoic acid
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of 4-(2-(2,6-dimethylphenylamino)-2-oxoethylamino)-N-(substituted)butanamides: A pharmacophoric hybrid approach

  摘要：

  A series of pharmacoplioric hybrids of ameltolide-gamma-aminobutyric acid (GABA)-amides was designed, synthesized, and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonVUlsant screening was performed using intraperitoneal (ip) maximal electrosbock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ), and subcutaneous picrotoxin (scPIC)induced seizure threshold tests. All the compounds had improved lipophilicity and the pharmacological activity profile confirmed their blood-brain barrier penetration. The titled compounds showed promising activity in scPIC screen indicating the involvement of GABA-mediation. Compound 4-(2-(2,6-dimetbylaminophenylamino)-2-oxoethylamino)-N-(2,6-dimethylphenyl) butanamide (7) emerged as the most potent derivative effective in all the three animal models of seizure with no neurotoxicity at the anticonvulsant dose. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.04.032

文献信息

• Synthesis and anticonvulsant activity of 4-(2-(2,6-dimethylphenylamino)-2-oxoethylamino)-N-(substituted)butanamides: A pharmacophoric hybrid approach
  作者：Perumal Yogeeswari、Dharmarajan Sriram、Puppala Sahitya、Jegadeesan Vaigunda Ragavendran、Velagaleti Ranganadh

  DOI：10.1016/j.bmcl.2007.04.032

  日期：2007.7

  A series of pharmacoplioric hybrids of ameltolide-gamma-aminobutyric acid (GABA)-amides was designed, synthesized, and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonVUlsant screening was performed using intraperitoneal (ip) maximal electrosbock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ), and subcutaneous picrotoxin (scPIC)induced seizure threshold tests. All the compounds had improved lipophilicity and the pharmacological activity profile confirmed their blood-brain barrier penetration. The titled compounds showed promising activity in scPIC screen indicating the involvement of GABA-mediation. Compound 4-(2-(2,6-dimetbylaminophenylamino)-2-oxoethylamino)-N-(2,6-dimethylphenyl) butanamide (7) emerged as the most potent derivative effective in all the three animal models of seizure with no neurotoxicity at the anticonvulsant dose. (c) 2007 Published by Elsevier Ltd.