allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate | 113599-83-0

• 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>-3-<2-(phenylseleno)ethyl>-8-oxo-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-(2-phenylselanylethyl)-4-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 113599-83-0
• 化学式: C₃₀H₃₁N₃O₈Se
• 分子量: 640.551
• InChiKey: VJFQDMZJDSMCGN-GPXOXTDOSA-N

物化性质

• 沸点：
  854.7±65.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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>-3-<2-(phenylseleno)ethyl>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 吡啶 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 以81%的产率得到allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-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
• 作为产物：
  描述：

  D(-)-对羟基苯甘氨酸 在 sodium hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 1,4-二氧六环 、 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-<2-(phenylseleno)ethyl>-8-oxo-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：——