(4-乙酰基苯基)氨基甲酰甲酸 | 6345-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-乙酰基苯基)氨基甲酰甲酸
• 英文名称: [(4-Acetylphenyl)amino](oxo)acetic acid
• 英文别名: 2-(4-acetylanilino)-2-oxoacetic acid
• CAS: 6345-10-4
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: YJZAICGKDZCJBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (4-乙酰基苯基)氨基甲酰甲酸 在 吡啶 、 sodium hydroxide 、 碘 作用下， 生成 N-{4-[4-(Oxalyl-amino)-phenyl]-thiazol-2-yl}-oxalamic acid
  参考文献：
  名称：

  N-（4-取代-噻唑基）草酰胺酸衍生物，一系列有效的口服活性抗过敏药。

  摘要：

  合成了一系列的N-（4-取代的噻唑基）草酰胺酸衍生物，并在大鼠PCA模型中测试了其抗过敏活性。这些化合物可通过用硫脲和碘处理适当的苯乙酮或使氯乙酰苯与硫脲反应生成相应的氨基噻唑来方便地制备。随后与乙二酰氯缩合，得到噻唑基草酸酯。许多类似物在低于2 mg / kg po或低于0.4 mg / kg iv时显示出50％的抑制作用，并且比色甘酸二钠显着更有效，后者在大鼠PCA模型中是口服失活的，并在50％时抑制。 1.2 mg / kg iv。草酸盐的水解通常会增强活性，而苯环则被各种取代基（例如4-F，4-OEt，和4-NHCOCH 3）没有显着增强未取代苯基衍生物的活性。已选择一种乙醇胺盐，N- [4-（1,4-苯并二恶烷-6-基）-2-噻唑基]乙酰胺酸乙醇胺盐（61，PRH-836-EA）进行进一步的药理评估。

  DOI：

  10.1021/jm00362a014
• 作为产物：
  描述：

  4-氨基苯乙酮 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (4-乙酰基苯基)氨基甲酰甲酸
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1

  摘要：

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.

  DOI：

  10.1021/jm3002247

文献信息

• Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1
  作者：Francesca Curreli、Spreeha Choudhury、Ilya Pyatkin、Victor P. Zagorodnikov、Anna Khulianova Bulay、Andrea Altieri、Young Do Kwon、Peter D. Kwong、Asim K. Debnath

  DOI：10.1021/jm3002247

  日期：2012.5.24

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.
• N-(4-Substituted-thiazolyl)oxamic acid derivatives, new series of potent, orally active antiallergy agents
  作者：Karl D. Hargrave、Friedrich K. Hess、James T. Oliver

  DOI：10.1021/jm00362a014

  日期：1983.8

  showed a 50% inhibition at less than 2 mg/kg po or less than 0.4 mg/kg iv and were significantly more potent than disodium cromoglycate, which in the rat PCA model is orally inactive and gives a 50% inhibition at 1.2 mg/kg iv. Hydrolysis of the oxamates generally resulted in enhanced activities, while substitution of the phenyl ring with a variety of substituents (e.g., 4-F, 4-OEt, and 4-NHCOCH3) did

  合成了一系列的N-（4-取代的噻唑基）草酰胺酸衍生物，并在大鼠PCA模型中测试了其抗过敏活性。这些化合物可通过用硫脲和碘处理适当的苯乙酮或使氯乙酰苯与硫脲反应生成相应的氨基噻唑来方便地制备。随后与乙二酰氯缩合，得到噻唑基草酸酯。许多类似物在低于2 mg / kg po或低于0.4 mg / kg iv时显示出50％的抑制作用，并且比色甘酸二钠显着更有效，后者在大鼠PCA模型中是口服失活的，并在50％时抑制。 1.2 mg / kg iv。草酸盐的水解通常会增强活性，而苯环则被各种取代基（例如4-F，4-OEt，和4-NHCOCH 3）没有显着增强未取代苯基衍生物的活性。已选择一种乙醇胺盐，N- [4-（1,4-苯并二恶烷-6-基）-2-噻唑基]乙酰胺酸乙醇胺盐（61，PRH-836-EA）进行进一步的药理评估。