4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸,6-(乙酰基氨基)-3,3-二甲基-7-羰基-,(2S,5R,6R)- | 15493-53-5

• 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
• 中文名称: 4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸,6-(乙酰基氨基)-3,3-二甲基-7-羰基-,(2S,5R,6R)-
• 英文名称: Methylpenicillin
• 英文别名: 6β-acetylamino-penicillanic acid；(2S,5R,6R)-6-Acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 15493-53-5
• 化学式: C₁₀H₁₄N₂O₄S
• 分子量: 258.298
• InChiKey: FKKLEFAXOOUTAS-GKROBHDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸,6-(乙酰基氨基)-3,3-二甲基-7-羰基-,(2S,5R,6R)- 在 oxoglutarate 、 recombinant Streptomyces clavuligerus DAOCS 、 iron(II) sulfate 作用下， 以 水 为溶剂， 生成 (5R,6R)-6-Acetylamino-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase

  摘要：

  Deacetoxycephalosporin C synthase from Streptomyces clavuligerus catalyses the conversion of the five-membered penicillin ring to the unsaturated six-membered cephem ring of deacetoxycephalosporin C. The effects on enzyme activity of the penicillin substrate sidechain and various cofactors were investigated using a continuous spectrophotometric assay. The conversion of penicillin G to phenylacetyl-7-aminodeacetoxycephalo sporanic acid (G-7-ADCA) was confirmed, and further details of the reaction were elucidated. The conversion of ampicillin to cephalexin was faster than that of acetyl-6-APA to acetyl-7-ADCA k(cat) = 0.120 +/- 0.001 s(-1) versus 0.035 +/- 0.001 s(-1), but they had similar K-m values: 4.86 +/- 0.12 and 3.28 +/- 0.26 mM, respectively. Amoxycillin and penicillin V were also converted at low levels. Conversion was not detected for penicillanate, 6-aminopenicillanate, carbenicillin, temocillin, ticarcillin or benzylpenicilloic acid, suggesting that the enzyme has a relatively strict selectivity for the sidechain of the penicillin substrate.

  DOI：

  10.1007/pl00000904

文献信息

• Synthesis, Spectroscopic Characteristics and Antibacterial Study of Some Novel Sulphonamides
  作者：Hajira Rehman、Abdul Qadir、Zulfiqar Ali、Nasir Mahmood、Asmat Zahra、Habib Hussain、Tanzeela Gulab Shahzady

  DOI：10.14233/ajchem.2016.19316

  日期：——

  Main purpose of this study was to produce some novel sulfonamides from already existing antibiotics having-NH2 group in their structure by their simple and low-cost condensation reactions with p-toulene sulfonyl chloride. All reactions were carried out in aqueous media at controlled pH (8-10) with good yield. Characterization of synthesized compounds were done by using FTIR, 1H NMR, ESI-MS and elemental analysis. Biological activity was evaluated against medically important Gram-positive and Gram-negative bacterial strains using MIC method after observing optical density value by spectrophotometer at 600 nm. All compounds were active against E. coli with MIC value less than 55 μg/mL, while N-((2S,5R,6R)-2-formyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptanes-6-yl)-N-tosylacetamide (1) showed pronounced results having MIC value less than 6 μg/mL for both strains.

  本研究的主要目的是通过简单、低成本的对甲苯磺酰氯缩合反应，从结构中含有 NH2 基团的现有抗生素中制备一些新型磺酰胺类药物。所有反应均在 pH 值可控（8-10）的水介质中进行，产率良好。利用傅立叶变换红外光谱、1H NMR、ESI-MS 和元素分析对合成的化合物进行了表征。通过分光光度计在 600 纳米波长下观察光密度值，采用 MIC 法评估了这些化合物对医学上重要的革兰氏阳性和革兰氏阴性细菌菌株的生物活性。所有化合物对大肠杆菌均有活性，其 MIC 值小于 55 μg/mL，而 N-((2S,5R,6R)-2-甲酰基-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-6-基)-N-对甲基苯磺酰乙酰胺（1）对两种菌株的 MIC 值均小于 6 μg/mL，显示出明显的效果。
• Improvements in or relating to beta lactam production
  申请人：BIOCHEMIE GESELLSCHAFT M.B.H.

  公开号：EP0439096B1

  公开（公告）日：2003-12-17
• SILYLATION PROCESS
  申请人：BIOCHEMIE GESELLSCHAFT M.B.H.

  公开号：EP0793666A1

  公开（公告）日：1997-09-10
• US3715347A
  申请人：——

  公开号：US3715347A

  公开（公告）日：1973-02-06
• US3994885A
  申请人：——

  公开号：US3994885A

  公开（公告）日：1976-11-30