7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin | 83421-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin
• 英文别名: trimethylsilyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 83421-24-3
• 化学式: C₁₇H₂₂IN₅O₅S₂Si
• 分子量: 595.514
• InChiKey: QFUNVQDFFVZOSY-PCZSKDDWSA-N

物化性质

• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin 在 四氢呋喃 、 甲醇 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 <6R-<6α,7β(Z)>>-1-<<7-<<(2-amino-4-thiazolyl)(methoxyimino)acetyl>amino>-2-carboxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-3-yl>methyl>-4-<3-carboxy-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl>-1-methylpiperazinium iodide
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quaternary ammonium quinolones

  摘要：

  When cephalosporins exert their biological activity by reacting with bacterial enzymes, opening of the beta-lactam ring can lead to expulsion of the 3'-substituent. A series of cephalosporins was prepared in which antibacterial quinolones were linked to the 3'-position through a quaternary nitrogen. Like the 3'-ester-linked dual-action cephalosporins reported earlier, these compounds demonstrated a broad spectrum of antibacterial activity derived from cephalosporin-like and quinolone-like components, suggesting a dual mode of action.

  DOI：

  10.1021/jm00106a031
• 作为产物：
  描述：

  在 碘代三甲硅烷 作用下， 反应 2.0h， 生成 7β-<2-(2-aminothiazol-4yl)-2-(Z)-methoximinoacetamide>-3-iodomethyl-2-<(trimethylsilyloxy)carbonyl>cephalosporin
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quaternary ammonium quinolones

  摘要：

  When cephalosporins exert their biological activity by reacting with bacterial enzymes, opening of the beta-lactam ring can lead to expulsion of the 3'-substituent. A series of cephalosporins was prepared in which antibacterial quinolones were linked to the 3'-position through a quaternary nitrogen. Like the 3'-ester-linked dual-action cephalosporins reported earlier, these compounds demonstrated a broad spectrum of antibacterial activity derived from cephalosporin-like and quinolone-like components, suggesting a dual mode of action.

  DOI：

  10.1021/jm00106a031

文献信息

• Synthesis and biological evaluation of a series of parenteral 3'-quaternary ammonium cephalosporins
  作者：Raymond F. Brown、Michael D. Kinnick、John M. Morin、Robert T. Vasileff、Fred T. Counter、Edward O. Davidson、Paul W. Ensminger、Judith A. Eudaly、Jeffrey S. Kasher

  DOI：10.1021/jm00170a011

  日期：1990.8

  The preparation and biological evaluation of a series of 7 beta-[2-(2-aminothiazol-4-yl)-2(Z)-methoximinoacetamido]cep halosporins, substituted at the 3'-position with monocyclic or bicyclic nitrogen-containing heterocycles are described. The resulting family of parenteral compounds displays a broad spectrum of antibacterial activity. Some compounds exhibit a similar level of Gram-negative activity to that of the "third-generation" cephalosporins with increased staphylococcal activity. The in vitro and in vivo antimicrobial activity, structure-activity relationships, beta-lactamase stability, and in vitro and in vivo pharmacological evaluations are presented.
• Synthesis and structure–activity relationships of quaternary ammonium cephalosporins with 3-pyrazolylpyridinium derivatives
  作者：Kwan Young Chang、Sung Hoon Kim、Ghilsoo Nam、Jae Hong Seo、Joong Hyup Kim、Deok-Chan Ha

  DOI：10.1016/s0960-894x(00)00203-1

  日期：2000.6

  Cephalosporins with 3-pyazolylpyridinium at C-3 position, which is supposed to exhibit synergic activity of ceftazidime and cefoselis, were synthesized and their antibacterial activity against Gram-positive and Gram-negative was inspected. (C) 2000 Elsevier Science Ltd. All rights reserved.
• New Cephalosporin Antibiotics with 3-Triazolylpyridiniummethyl Substituents.
  作者：KWAN YOUNG CHANG、SOON HO KWON、GHILSOO NAM、JAE HONG SEO、SUNG HOON KIM、KYUNG IL CHOI、JOONG HYUP KIM、DEOK-CHAN HA

  DOI：10.7164/antibiotics.54.460

  日期：——
• BROWN, RAYMOND F.;KINNICK, MICHAEL D.;MORIN, JOHN M. (JR);VASILEFF, ROBER+, J. MED. CHEM., 33,(1990) N, C. 2114-2121
  作者：BROWN, RAYMOND F.、KINNICK, MICHAEL D.、MORIN, JOHN M. (JR)、VASILEFF, ROBER+

  DOI：——

  日期：——