tert-butyl 7β-amino-3-methyl-1,1-dioxoceph-3-em-4-carboxylate | 190514-40-0

• 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: tert-butyl 7β-amino-3-methyl-1,1-dioxoceph-3-em-4-carboxylate
• 英文别名: t-butyl 7β-amino-3-methyl-3-cephem-4-carboxylate 1,1-dioxide；tert-butyl 7-amino-deacetoxycephalosporanoate 1,1-dioxide；tert-butyl (6R,7R)-7-amino-3-methyl-5,5,8-trioxo-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；tert-butyl (6R,7R)-7-amino-3-methyl-5,5,8-trioxo-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 190514-40-0
• 化学式: C₁₂H₁₈N₂O₅S
• 分子量: 302.351
• InChiKey: XPUBUTQFLMUCNZ-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 7β-amino-3-methyl-1,1-dioxoceph-3-em-4-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 亚硝酸异丙酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 25.5h， 生成 tert-butyl (6R,7S)-3-[[2-[2-(2,6-dichloroanilino)phenyl]acetyl]oxymethyl]-7-methoxy-5,5,8-trioxo-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  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：

  t-butyl 7α-amino-3-methyl-3-cephem-4-carboxylate 在 sodium tungstate 双氧水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到tert-butyl 7β-amino-3-methyl-1,1-dioxoceph-3-em-4-carboxylate
  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

• Synthesis and evaluation of dual action cephalosporins as elastase inhibitors
  作者：Grigory Veinberg、Irina Shestakova、Larisa Petrulanis、Nora Grigan、Dan Musel、Dairis Zeile、Iveta Kanepe、Ilona Domrachova、Ivars Kalvinsh、Andris Strakovs、Edmunds Lukevics

  DOI：10.1016/s0960-894x(97)00104-2

  日期：1997.1

  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.
• Cephalosporin Podand Derivatives.
  作者：ÁRPÁD KOVÁCS-KULYASSA、PÁL HERCZEGH、FERENC J. SZTARICSKAI、PÁL SZABÓ

  DOI：10.7164/antibiotics.53.1207

  日期：——
• Synthesis and human leukocyte elastase inhibitory activity of novel 2-spiro(2′,2′-diphenylcyclopropane) cephalosporin sulfones
  作者：Andhe V. Narender Reddy、Charles Y. Fiakpui、David P. Czajkowski、Paul Spevak、Jadwiga Kaleta、Ronald G. Micetich、Samarendra N. Maiti

  DOI：10.1007/bf02256809

  日期：1998.11
• Synthesis and structural modification of tert-butyl ester of 7α-chloro-2-(N,N-dimethylaminomethylene)-3-methyl-1,1-dioxoceph-3-em-4-carboxylic acid
  作者：M. Vorona、I. Potoročina、G. Veinberg、I. Shestakova、I. Kanepe、M. Petrova、E. Liepinsh、E. Lukevics

  DOI：10.1007/s10593-007-0101-2

  日期：2007.5