tert-butyl (2R,6R,7R)-3-(hydroxymethyl)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate | 219901-34-5

• 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: tert-butyl (2R,6R,7R)-3-(hydroxymethyl)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate
• CAS: 219901-34-5
• 化学式: C₁₇H₂₆N₂O₆S
• 分子量: 386.469
• InChiKey: NGLGUZTUBLDIQE-NQBHXWOUSA-N

物化性质

• 沸点：
  575.4±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,6R,7R)-3-(hydroxymethyl)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate 在 sodium tungstate 亚硝酸异丙酯 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 51.62h， 生成
  参考文献：
  名称：

  New biological properties of tert-butyl cephalosporanate sulfones

  摘要：

  tert-Butyl cephalosporanate I,l-dioxides variously substituted in positions 7 and 3 were obtained from 7-aminodeacetoxycephalosporanic acid (7-ADCA) and 7-aminocephalosporanic acid (7 ACA). It was found that the cephalosporins containing Aspirin and Diclofenac in a prodrug form in their 3-acyloxymethyl moiety release them after hydrolytic splitting of the beta-lactam ring. They also demonstrated high efficacy as elastase inhibitors. Two of them stimulated the biosynthesis of nitric oxide in RAW 264.7 macrophages cells. The same effect observed in tumor and normal cells in the presence of cephalosporins was accompanied by cytotoxic effect in vitro. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80027-0
• 作为产物：
  描述：

  7-氨基头孢烷酸 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 生成 tert-butyl (2R,6R,7R)-3-(hydroxymethyl)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis of N,O-disubtituted 3-hydroxymethyl-7-Aminocephalosporanic acid

  摘要：

  DOI：

  10.1007/bf01169364

文献信息

• New biological properties of tert-butyl cephalosporanate sulfones
  作者：Grigory Veinberg、Irina Shestakova、Nora Grigan、Dan Musel、Iveta Kanepe、Ilona Domrachova、Vera Grigoryeva、Olga Zharkova、Ivars Turovskis、Ivars Kalvinsh、Andris Strakovs、Edmunds Lukevics

  DOI：10.1016/s0223-5234(99)80027-0

  日期：1998.10

  tert-Butyl cephalosporanate I,l-dioxides variously substituted in positions 7 and 3 were obtained from 7-aminodeacetoxycephalosporanic acid (7-ADCA) and 7-aminocephalosporanic acid (7 ACA). It was found that the cephalosporins containing Aspirin and Diclofenac in a prodrug form in their 3-acyloxymethyl moiety release them after hydrolytic splitting of the beta-lactam ring. They also demonstrated high efficacy as elastase inhibitors. Two of them stimulated the biosynthesis of nitric oxide in RAW 264.7 macrophages cells. The same effect observed in tumor and normal cells in the presence of cephalosporins was accompanied by cytotoxic effect in vitro. (C) Elsevier, Paris.
• Synthesis of N,O-disubtituted 3-hydroxymethyl-7-Aminocephalosporanic acid
  作者：G. A. Veinberg、L. N. Petrulyanis、N. Grigan、I. V. Turovskii、D. I. Musel'、E. Lukevic

  DOI：10.1007/bf01169364

  日期：1996.1