2-methoxy-3-(methylcarbamoyl)-4-pivalamidobenzoicacid | 1383452-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-3-(methylcarbamoyl)-4-pivalamidobenzoicacid
• 英文别名: 4-(2,2-Dimethylpropanoylamino)-2-methoxy-3-(methylcarbamoyl)benzoic acid
• CAS: 1383452-10-5
• 化学式: C₁₅H₂₀N₂O₅
• 分子量: 308.334
• InChiKey: BARVOMVUBFMAKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-(methylcarbamoyl)-4-pivalamidobenzoicacid 在 盐酸 、 magnesium sulfate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 N-(4-fluorobenzyl)-5-methoxy-3-methyl-4-oxo-2-(thiophen-2-yl)-1,2,3,4-tetrahydroquinazoline-6-carboxamide
  参考文献：
  名称：

  Design, synthesis and antiviral activity of novel quinazolinones

  摘要：

  HIV-1 integrase (IN) is a validated therapeutic target for antiviral drug design. However, the emergence of viral strains resistant to clinically studied IN inhibitors demands the discovery of novel inhibitors that are structurally as well as mechanistically different. Herein, a series of quinazolinones were designed and synthesized as novel HIV-1 inhibitors. The new synthetic route provides a practical method for the preparation of 5-hydroxy quinazolinones. Primary bioassay results indicated that most of the quinazolinones possess anti-HIV activity, especially for compound 11b with 77.5% inhibition rate at 10 mu M emerged as a new active lead. Most of the synthesized compounds were also found to exhibit good anti-TMV activity, of which compound 9a showed similar in vivo anti-TMV activity to commercial plant virucide Ribavirin. This work provides a new and efficient approach to evolve novel multi-functional antiviral agents by rational integration and optimization of previously reported antiviral agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.010
• 作为产物：
  描述：

  N-(3-hydroxy-4-methylphenyl)-2,2-dimethylpropionamide 在 吡啶 、 potassium permanganate 、 正丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 mineral oil 为溶剂， 反应 18.5h， 生成 2-methoxy-3-(methylcarbamoyl)-4-pivalamidobenzoicacid
  参考文献：
  名称：

  Design, synthesis and antiviral activity of novel quinazolinones

  摘要：

  HIV-1 integrase (IN) is a validated therapeutic target for antiviral drug design. However, the emergence of viral strains resistant to clinically studied IN inhibitors demands the discovery of novel inhibitors that are structurally as well as mechanistically different. Herein, a series of quinazolinones were designed and synthesized as novel HIV-1 inhibitors. The new synthetic route provides a practical method for the preparation of 5-hydroxy quinazolinones. Primary bioassay results indicated that most of the quinazolinones possess anti-HIV activity, especially for compound 11b with 77.5% inhibition rate at 10 mu M emerged as a new active lead. Most of the synthesized compounds were also found to exhibit good anti-TMV activity, of which compound 9a showed similar in vivo anti-TMV activity to commercial plant virucide Ribavirin. This work provides a new and efficient approach to evolve novel multi-functional antiviral agents by rational integration and optimization of previously reported antiviral agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.010