allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate | 113599-91-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: prop-2-enyl (6S,7S)-7-[[(2R)-2-(4-hydroxyphenyl)-2-(prop-2-enoxycarbonylamino)acetyl]amino]-8-oxo-3-prop-2-enyl-4-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 113599-91-0
• 化学式: C₂₅H₂₇N₃O₈
• 分子量: 497.505
• InChiKey: ZHSHSSBVSYNLAF-RLLQIKCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  143.5
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 四(三苯基膦)钯 、 2-乙基-己酸稀土盐 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020
• 作为产物：
  描述：

  烯丙基2-溴乙酸乙酯 在 吡啶 、 3,4-二氢-2H-吡喃 、 氢氧化钾 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 四丁基溴化铵 、 碳酸氢钠 、 对甲苯磺酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 间氯过氧苯甲酸 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(2-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020

文献信息

• MASTALERZ, HAROLD;MENARD, MARCEL;VINET, VIVIANNE;DESIDERIO, JAMES;FUNG-TO+, J. MED. CHEM., 31,(1988) N 6, 1190-1196
  作者：MASTALERZ, HAROLD、MENARD, MARCEL、VINET, VIVIANNE、DESIDERIO, JAMES、FUNG-TO+

  DOI：——

  日期：——