diphenylmethyl 7β-amino-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate | 103574-53-4

• 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: diphenylmethyl 7β-amino-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate
• CAS: 103574-53-4
• 化学式: C₂₆H₂₃N₃O₃S₂
• 分子量: 489.619
• InChiKey: AGOTWQNKMDBPPO-PXDATVDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.52
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7β-amino-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate 在 苯磺酰胺 、 水 、 碳酸氢钠 、 氯化铵 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 苯甲醚 为溶剂， 反应 3.5h， 生成 (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(pyridin-3-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-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：

  diphenylmethyl 7β-formamido-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 以94%的产率得到diphenylmethyl 7β-amino-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylate
  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