7-diazodesacetoxycephalosporanic acid tert-butyl ester sulfone | 190514-41-1

• 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: 7-diazodesacetoxycephalosporanic acid tert-butyl ester sulfone
• CAS: 190514-41-1
• 化学式: C₁₂H₁₅N₃O₅S
• 分子量: 313.334
• InChiKey: ZGMKIBVEAMNHNZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  117.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-diazodesacetoxycephalosporanic acid tert-butyl ester sulfone 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 25.5h， 生成 tert-butyl (6R,7S)-3-[(2-acetyloxybenzoyl)oxymethyl]-7-chloro-5,5,8-trioxo-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of dual action cephalosporins as elastase inhibitors

  摘要：

  tert-Butyl 7 alpha-chloro- and 7 alpha-methoxycephalosporanate 1,1-dioxides containing Aspirin and Diclofenac in their 3-acyloxymethyl moiety were synthesized. These dual action cephalosporins have been found to be potent elastase inhibitors and stimulators of NO biosynthesis in macrophages. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00104-2
• 作为产物：
  描述：

  tert-butyl 7β-amino-3-methyl-1,1-dioxoceph-3-em-4-carboxylate 在 亚硝酸异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 7-diazodesacetoxycephalosporanic acid tert-butyl ester sulfone
  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

文献信息

• Sulfones of 7-silyl- and 7-germylcephalosporanates
  作者：G. Veinberg、M. Vorona、D. Mucel'、Kh. Kazhoka、I. Shestakova、I. Kanepe、I. Domracheva、A. Strakov、E. Lukevics

  DOI：10.1007/bf02256807

  日期：1998.11