7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(E)-2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid | 288380-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(E)-2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid
• CAS: 288380-03-0
• 化学式: C₃₈H₃₀N₆O₅S₃
• 分子量: 746.891
• InChiKey: BKXXOQZKUMRKEL-AUBIFSNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  52.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  160.1
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(E)-2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid 在 甲酸 作用下， 反应 1.0h， 以29%的产率得到7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido]-3-[(E)-2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Orally active cephalosporins. Part 2: Synthesis, structure–activity relationships and oral absorption of cephalosporins having a C-3 pyridyl side chain

  摘要：

  A series of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]cephalosporins having a pyridine ring connected through various spacer moieties at the C-3 position was designed and synthesized and evaluated for antibacterial activity and oral absorption in rats. All compounds showed potent antibacterial activity against Staphylococcus aureus, whereas antibacterial activity against Gram-negative bacteria was markedly influenced by the spacer moiety between the pyridine and cephem nucleus. Oral absorption was influenced by the position of the pyridine nitrogen as well as by the spacer moiety. Among these compounds, FR86830 (14), having a 4-pyridylmethylthio moiety at the C-3 position, showed the most well balanced activity and moderate oral absorption. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00021-3
• 作为产物：
  描述：

  吡啶-4(1H)-硫酮 在 盐酸 、 甲酸 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.34h， 生成 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(E)-2-(4-pyridyl)thiovinyl]-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Orally active cephalosporins. Part 2: Synthesis, structure–activity relationships and oral absorption of cephalosporins having a C-3 pyridyl side chain

  摘要：

  A series of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]cephalosporins having a pyridine ring connected through various spacer moieties at the C-3 position was designed and synthesized and evaluated for antibacterial activity and oral absorption in rats. All compounds showed potent antibacterial activity against Staphylococcus aureus, whereas antibacterial activity against Gram-negative bacteria was markedly influenced by the spacer moiety between the pyridine and cephem nucleus. Oral absorption was influenced by the position of the pyridine nitrogen as well as by the spacer moiety. Among these compounds, FR86830 (14), having a 4-pyridylmethylthio moiety at the C-3 position, showed the most well balanced activity and moderate oral absorption. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00021-3