6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester | 36273-76-4

• 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: 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester
• 英文别名: Benzyl N-p-nitrobenzylidene-6-aminopenicillanate；benzyl-6-(p-nitrobenzylideneamino)penicillanate；Benzyl-6β-(p-Nitrobenzylidenamino)-penicillinat；benzyl (2S,5R,6R)-3,3-dimethyl-6-[(4-nitrophenyl)methylideneamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 36273-76-4
• 化学式: C₂₂H₂₁N₃O₅S
• 分子量: 439.492
• InChiKey: QHUJRHGQPLZBIB-WSTZPKSXSA-N

物化性质

• 沸点：
  634.8±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester 在 N-氯-N-吡啶基乙酰肼 、 对甲苯磺酸 、 苯基锂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 (5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 64.0h， 生成 6β-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x

文献信息

• Penicillin derivatives and compositions containing them
  申请人：Beecham Group Limited

  公开号：US04349551A1

  公开（公告）日：1982-09-14

  A compound of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolyzable ester thereof: ##STR1## wherein R is phenyl 4-hydroxy phenyl, or a 5- 6- membered heterocyclic ring containing up to three heteroatoms selected from oxygen, sulphur or nitrogen, optionally substituted with hydroxy, amino, halogen or C.sub.1-6 alkoxy; R.sup.1 represents hydrogen or C.sub.1-6 alkyl; R.sup.2 and R.sup.3 are the same or different and represent hydrogen, C.sub.1-6 alkyl, halogen, amino, hydroxy, or C.sub.1-6 alkoxy. Their preparation and use is described.

  化合物的化学式（I）或其药学上可接受的盐或体内可水解酯：##STR1## 其中R是苯基4-羟基苯基，或含有最多三个氧，硫或氮的5-6个成员杂环，可选择用羟基，氨基，卤素或C.sub.1-6烷氧基进行取代；R.sup.1代表氢或C.sub.1-6烷基；R.sup.2和R.sup.3相同或不同，代表氢，C.sub.1-6烷基，卤素，氨基，羟基或C.sub.1-6烷氧基。描述了它们的制备和用途。
• Penicillin 6,6′-dimer
  作者：Raymond A. Firestone、Natalie Schelechow、B. G. Christensen

  DOI：10.1039/c39720001106

  日期：——

  Treatment of the p-nitrobenzaldehyde Schiff base of 6-APA benzyl ester (I) with phenyl-lithium and then with oxygen affords the 6,6′-dimer (IV) and the nitrone (X).

  用苯基锂然后用氧气处理6-APA苄基酯（I）的对硝基苯甲醛席夫碱，得到6,6'-二聚体（IV）和硝酮（X）。
• Substituted penicillins and cephalosporins II. C-6(7)-alkyl derivatives (1)
  作者：Raymond A. Firestone、Natalie Schelechow、David B.R. Johnston、B.G. Christensen

  DOI：10.1016/s0040-4039(01)84328-8

  日期：1972.1
• 6-Substituted penicillin derivatives, VI
  作者：G.H. Rasmusson、G.F. Reynolds、G.E. Arth

  DOI：10.1016/s0040-4039(01)95600-x

  日期：1973.1
• Total synthesis of .beta.-lactam antibiotics. Epimerization of 6(7)-aminopenicillins and cephalosporins from .alpha. to .beta.
  作者：Raymond A. Firestone、Natalie S. Maciejewicz、Ronald W. Ratcliffe、B. G. Christensen

  DOI：10.1021/jo00918a003

  日期：1974.2