diphenylmethyl 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(acetoxyimino)acetamido]-3-(3-pyridylthio)-3-cephem-4-carboxylate | 163009-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: diphenylmethyl 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(acetoxyimino)acetamido]-3-(3-pyridylthio)-3-cephem-4-carboxylate
• 英文别名: benzhydryl (6R,7R)-7-[[(2Z)-2-acetyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-pyridin-3-ylsulfanyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 163009-25-4
• 化学式: C₃₂H₂₆N₆O₆S₃
• 分子量: 686.793
• InChiKey: FTSOROJPJRCNRK-IWVGHOLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  245
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(acetoxyimino)acetamido]-3-(3-pyridylthio)-3-cephem-4-carboxylate 在 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-ylsulfanyl-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：

  吡啶-3-硫醇 在 盐酸 、 苯磺酰胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 diphenylmethyl 7β-[2-(Z)-(2-aminothiazol-4-yl)-2-(acetoxyimino)acetamido]-3-(3-pyridylthio)-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

文献信息

• [EN] NEW CEPHEM COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES DE CEPHEME
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1995007283A1

  公开（公告）日：1995-03-16

  (EN) New cephem compounds of formula (I), wherein R1 is amino or protected amino, R2 is hydrogen, lower alkyl or hydroxy protective group, R3 is carboxy or protected carboxy, R4 is 3-pyridyl, 4-pyridyl or optionally substituted heteromonocyclic group containing two nitrogen atoms as hetero atoms, and which may also contain one oxygen or sulfur atom, and n is 0, 1 or 2, provided that when R2 is lower alkyl, then n is 1 or 2 and R4 is optionally substituted heteromonocyclic group containing two nitrogen atoms as hetero atoms, and which may also contain one oxygen or sulfur atom, and pharmaceutically acceptable salts thereof which are useful as a medicament.(FR) L'invention porte sur des nouveaux composés céphème représentés par la formule suivante: (I) dans laquelle R1 représente amino ou amino protégé, R2 représente hydrogène, alkyle inférieur ou un groupe protecteur hydroxy, R3 représente carboxy ou carboxy protégé, R4 représente 3-pyridyle, 4-pyridyle ou un groupe hétéromonocyclique éventuellement substitué contenant deux atomes d'azote en tant qu'hétéroatomes et pouvant également contenir un atome d'oxygène ou de soufre, et n correspond à 0, 1 ou 2, à condition que, lorsque R2 représente alkyle inférieur, n corresponde à 1 ou 2, et R4 représente un groupe hétéromonocyclique contenant deux atomes d'azote en tant qu'hétéroatomes et pouvant également contenir un atome d'oxygène ou de soufre. L'invention se rapporte également à des sels pharmaceutiquement acceptables desdits composés pouvant être utilisés en tant que médicament.

  新的头孢菌素化合物的化学式为（I），其中R1为氨基或保护的氨基，R2为氢、低碳基或羟基保护基，R3为羧基或保护的羧基，R4为3-吡啶基、4-吡啶基或可选取代的含有两个氮原子作为杂原子的杂单环族基，且可能还包含一个氧或硫原子，n为0、1或2，但当R2为低碳基时，n为1或2，且R4为可选取代的含有两个氮原子作为杂原子的杂单环族基，且可能还包含一个氧或硫原子。这些化合物的药物可接受的盐可用作药物。
• NEW CEPHEM COMPOUNDS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0667868A1

  公开（公告）日：1995-08-23
• US6468995B1
  申请人：——

  公开号：US6468995B1

  公开（公告）日：2002-10-22