7-<(2-aminothiazol-4-yl)acetamido>-3-chloro-3-cephem-4-carboxylic acid | 110425-20-2

• 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: 7-<(2-aminothiazol-4-yl)acetamido>-3-chloro-3-cephem-4-carboxylic acid
• 英文别名: 7-[(2-aminothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid；7-(((2-Amino-4-thiazolyl)acetyl)amino)-3-chloro-3-cephem-4-carboxylic acid；(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 110425-20-2
• 化学式: C₁₂H₁₁ClN₄O₄S₂
• 分子量: 374.829
• InChiKey: FXNJFBGXXJAMQB-GMSGAONNSA-N

物化性质

• 沸点：
  809.8±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-氨基-3-氯-3-头孢环-4-羧酸 在 甲酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 7-<(2-aminothiazol-4-yl)acetamido>-3-chloro-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Oral absorption of cephalosporin antibiotics. 1. Synthesis, biological properties and oral bioavailability of 7-arylacetamido-3-chloro cephalosporins in animals

  摘要：

  A number of 7-(arylacetamido)-3-substituted cephalosporins were prepared and tested in animals for oral absorbability. Bioavailability in mice, rats, dogs, and monkeys was determined after oral or parenteral administration. Oral bioavailability of five compounds selected for more intensive study was generally higher than that of penicillin V in all species tested. The results of ED50 testing against experimental infections in mice generally supported the bioavailability studies. Antibiotic activities were evaluated against Gram-positive and Gram-negative organisms with some derivatives expressing in vitro activity similar to cefaclor. The plasma half-life in rats was relatively short and the plasma curves were strongly influenced by probenecid, indicating rapid renal secretion. Some 7-(arylacetamido)-3-chloro cephalosporins are orally absorbed in animals to a greater extent than penicillin V, and antibacterial agent of proven clinical utility.

  DOI：

  10.1021/jm00118a022

文献信息

• Cephalosporins, their preparation and formulations
  申请人：ELI LILLY AND COMPANY

  公开号：EP0211526A2

  公开（公告）日：1987-02-25

  7p-Heterocyclicacetylamino-(and 7β-heterocyclic- thioacetamido)-3-chloro-3-cephem-4-carboxylic acids or pharmaceutically acceptable salts thereof (e.g., 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid and salts thereof) exhibit surprising peroral bioavailability and are useful for treating infections in a warm-blooded animal. The have the formula in which R is a 5-membered nitrogen-containing heterocyclic ring of the formulae or Y is S or a bond; in which in the above formulae Z is O, S, or N and R' is hydrogen, hydroxy, halo, amino, C1-C4 alkanoylamino, C1-C4 alkylamino, di-(C1-C4 alkyllamino, C1-C4 alkylsulfonylamino, C1-C4 alkanoyloxy, C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 alkyl, phenyl, or trihalomethyl; R1 is hydrogen, methoxy, or formamido; or a pharmaceutically acceptable salt thereof.

  7p-杂环乙酰氨基-（和 7β-杂环-硫代乙酰氨基）-3-氯-3-头孢-4-羧酸或其药学上可接受的盐（例如，7β-[2-（2-氨基噻唑-4-基）乙酰氨基]-3-氯-3-头孢-4-羧酸及其盐）具有惊人的口服生物利用度，可用于治疗温血动物的感染。它们的化学式为 其中 R 是式中的 5 元含氮杂环 或 Y 是 S 或键； 其中上式中 Z 是 O、S 或 N，R'是氢、羟基、卤代、氨基、C1-C4 烷酰氨基、C1-C4 烷基氨基、二（C1-C4 烷基氨基、C1-C4 烷基磺酰氨基、C1-C4 烷酰氧基、C1-C4 烷氧基、C1-C4 烷基磺酰氧基、C1-C4 烷基、苯基或三卤甲基； R1 是氢、甲氧基或甲酰胺基；或其药学上可接受的盐。
• KUKOLJA, STJEPAN;WRIGHT, WALTER E.;QUAY, JOHN F.;PFEIL-DOYLE, JANICE;DRAH+
  作者：KUKOLJA, STJEPAN、WRIGHT, WALTER E.、QUAY, JOHN F.、PFEIL-DOYLE, JANICE、DRAH+

  DOI：——

  日期：——
• US4683227A
  申请人：——

  公开号：US4683227A

  公开（公告）日：1987-07-28
• Oral absorption of cephalosporin antibiotics. 1. Synthesis, biological properties and oral bioavailability of 7-arylacetamido-3-chloro cephalosporins in animals
  作者：Stjepan Kukolja、Walter E. Wright、John F. Quay、Janice Pfeil-Doyle、Susan E. Draheim、Judith Ann Eudaly、Roderick J. Johnson、John L. Ott、Fred T. Counter

  DOI：10.1021/jm00118a022

  日期：1988.10

  A number of 7-(arylacetamido)-3-substituted cephalosporins were prepared and tested in animals for oral absorbability. Bioavailability in mice, rats, dogs, and monkeys was determined after oral or parenteral administration. Oral bioavailability of five compounds selected for more intensive study was generally higher than that of penicillin V in all species tested. The results of ED50 testing against experimental infections in mice generally supported the bioavailability studies. Antibiotic activities were evaluated against Gram-positive and Gram-negative organisms with some derivatives expressing in vitro activity similar to cefaclor. The plasma half-life in rats was relatively short and the plasma curves were strongly influenced by probenecid, indicating rapid renal secretion. Some 7-(arylacetamido)-3-chloro cephalosporins are orally absorbed in animals to a greater extent than penicillin V, and antibacterial agent of proven clinical utility.