4.4'-Bis(acetoacetamido)diphenylsulfone | 30764-26-2

• 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: 4.4'-Bis(acetoacetamido)diphenylsulfone
• 英文别名: N1-4-[4-(2-oxopropylcarboxamido)phenylsulphonyl]phenyl-3-oxobutanamide；N,Na(2)-(Sulfonyldi-4,1-phenylene)bis[3-oxobutanamide]；3-oxo-N-[4-[4-(3-oxobutanoylamino)phenyl]sulfonylphenyl]butanamide
• CAS: 30764-26-2
• 化学式: C₂₀H₂₀N₂O₆S
• 分子量: 416.455
• InChiKey: BBCAYNHFDMILDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 盐酸胍 、 4.4'-Bis(acetoacetamido)diphenylsulfone 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 以86%的产率得到2-imino-N-[4-[4-[[2-imino-4-methyl-6-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carbonyl]amino]phenyl]sulfonylphenyl]-4-methyl-6-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxamide
  参考文献：
  名称：

  Bis dihydropyrimidine: synthesis and antimycobacterial activity

  摘要：

  A series of bis dihydropyrimidine compounds were synthesised by reacting dapsone with acetylacetoacetate to produce N1-4-[4-(2-oxopropylcarboxamido) phenylsulphonyl] phenyl-3-oxobutanamide, then treated with guanidine hydrochloride and an appropriate aldehyde with a catalytic amount of p-toluene sulphonic acid (PTSA) in the presence of methanol to afford the title compounds. The synthesised compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv and isoniazid (INH) resistant M. tuberculosis. Among the synthesised compounds, compound N5-(4-4-[6-(4-fluorophenyl)-2-imino-4-methyl-1,2,3,4-tetrahydro-5-pyrimidinylcarboxamido ]phenylsulphonylphenyl)-6-(4-fluorophenyl)-2-imino-4-methyl-1,2,3,4-tetrahydro-5-pyrimidine carboxamide (3g) was found to be the most promising compound with activity against M. tuberculosis H(37)Rv and INH resistant M. tuberculosis with a minimum inhibitory concentration (MIC) between 0.08 and 0.10 mu mu M.

  DOI：

  10.3109/14756366.2010.482046
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 氨苯砜 反应 15.0h， 生成 4.4'-Bis(acetoacetamido)diphenylsulfone
  参考文献：
  名称：

  Bis dihydropyrimidine: synthesis and antimycobacterial activity

  摘要：

  A series of bis dihydropyrimidine compounds were synthesised by reacting dapsone with acetylacetoacetate to produce N1-4-[4-(2-oxopropylcarboxamido) phenylsulphonyl] phenyl-3-oxobutanamide, then treated with guanidine hydrochloride and an appropriate aldehyde with a catalytic amount of p-toluene sulphonic acid (PTSA) in the presence of methanol to afford the title compounds. The synthesised compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv and isoniazid (INH) resistant M. tuberculosis. Among the synthesised compounds, compound N5-(4-4-[6-(4-fluorophenyl)-2-imino-4-methyl-1,2,3,4-tetrahydro-5-pyrimidinylcarboxamido ]phenylsulphonylphenyl)-6-(4-fluorophenyl)-2-imino-4-methyl-1,2,3,4-tetrahydro-5-pyrimidine carboxamide (3g) was found to be the most promising compound with activity against M. tuberculosis H(37)Rv and INH resistant M. tuberculosis with a minimum inhibitory concentration (MIC) between 0.08 and 0.10 mu mu M.

  DOI：

  10.3109/14756366.2010.482046

文献信息

• POLYMERIC BIS-ACETOACETANILIDE AZO COLORANTS
  申请人：Milliken & Company

  公开号：EP1337591B1

  公开（公告）日：2010-06-02