cefpirome | 65243-49-4

• 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: cefpirome
• 英文别名: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 65243-49-4
• 化学式: C₁₉H₁₈N₆O₅S₂
• 分子量: 474.521
• InChiKey: DUSOHVGDHONLKB-ZKDACBOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  头孢噻肟 在 甲醇 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 cefpirome
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of parenteral 3'-quaternary ammonium cephalosporins

  摘要：

  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.

  DOI：

  10.1021/jm00170a011

文献信息

• Method for production of cephalosporin compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04980464A1

  公开（公告）日：1990-12-25

  A method for producing a compound of the formula; ##STR1## wherein R stands for a hydrogen atom, an acyl group or a protective group other than acyl groups, Q stands for a hydrogen atom or an ester residue, Y stands for the residue of a nucleophilic compound and the dotted line shows the double bond at 2- or 3- position of the cephem ring or a salt thereof, characterized by allowing a compound of the formula; ##STR2## [R, Q and the dotted line are of the same meaning as above] or a salt thereof to react with a nucleophilic compound or a salt thereof and a compound of the formula; ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 independently stand for a hydrocarbon group having not more than 8 carbon atoms, or R.sup.1 and R.sup.2, R.sup.1 and R.sup.3 or R.sup.2 and R.sup.3 may be combined to form polymethylene group, according to which the end product [I] of high quality can be provided in a high yield by one reaction step by using the compound [III] of relatively low cost, thus the method of this invention is advantageous for mass-producing the compound [I] on an industrial scale from the compound [II] and a nucleophilic compound.

  一种制备式为##STR1##的化合物或其盐的方法，其中R代表氢原子、酰基或除酰基以外的保护基，Q代表氢原子或酯残基，Y代表亲核化合物的残基，点线表示头孢环上2或3位的双键或其盐。该方法的特点在于，允许式为##STR2##[R、Q和点线的含义如上]或其盐与亲核化合物或其盐以及式为##STR3##其中R.sup.1、R.sup.2、R.sup.3独立地代表不超过8个碳原子的烃基，或R.sup.1和R.sup.2、R.sup.1和R.sup.3或R.sup.2和R.sup.3可以组成聚亚甲基基团反应，从而可以使用相对低成本的化合物[III]经过一步反应得到高产率的高质量终产品[I]，因此本发明的方法对于从化合物[II]和亲核化合物大规模工业生产化合物[I]具有优势。
• 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：——
• 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.