7-formylamino-3-acetoxymethyl-3-cephem-4-carboxylic acid | 27267-35-2

• 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-formylamino-3-acetoxymethyl-3-cephem-4-carboxylic acid
• 英文别名: 7-formamido-3-acetoxymethyl-3-cephem-4-carboxylic acid；7-N-formyl-cephalosporanic acid；(6R,7R)-3-acetoxymethyl-7-formamidoceph-3-em-4-carboxylic acid；7-formylamino-cephalosporanic acid；7-formamidocephalosporanic acid；3-Acetoxymethyl-7beta-formamidoceph-3-em-4-carboxylic acid；(6R,7R)-3-(acetyloxymethyl)-7-formamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 27267-35-2
• 化学式: C₁₁H₁₂N₂O₆S
• 分子量: 300.292
• InChiKey: WQTHHXUGFMYHEV-GMSGAONNSA-N

物化性质

• 沸点：
  678.9±55.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-formylamino-3-acetoxymethyl-3-cephem-4-carboxylic acid 在 盐酸 、 phosphate buffer 、 wheat bran 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 benzhydryl 7-formamido-3-N-methylcarbamoyloxymethyl-2-cephem-4-carboxylate
  参考文献：
  名称：

  口服活性头孢菌素的研究。I.新的3-取代的氨基甲酰氧基甲基头孢菌素的合成与构效关系。

  摘要：

  7β-[2-（2-氨基噻唑-4-基）-2-羟基亚氨基乙酰胺基] -3-N，N-二甲基氨基甲酰氧基甲基-3-cephem-4-羧酸（E1100）及其类似物的合成及抗菌活性为描述了1-（异丙氧基羰基氧基）乙基酯（E1101）及其类似酯的口服吸收性和体内活性。在3-氨基甲酰氧基甲基头孢烯的N-位引入无环和环状低级烷基会影响抗菌活性，特别是对流感嗜血杆菌的抗菌活性，以及​​它们的前药酯的口服吸收性。还讨论了结构-活性关系。

  DOI：

  10.7164/antibiotics.47.1507
• 作为产物：
  描述：

  (6R,7R)-7-[acetyl(formyl)amino]-3-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 以 水 为溶剂， 以94%的产率得到(6R,7R)-7-acetamido-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Spry, Douglas O.; Snyder, Nancy J.; Bhala, Anita R., Heterocycles, 1987, vol. 26, # 11, p. 2911 - 2920

  摘要：

  DOI：

文献信息

• Derivatives of
  申请人：SmithKline Corporation

  公开号：US04066762A1

  公开（公告）日：1978-01-03

  New semisynthetic cephalosporins are described whose structures are characterized by having an .alpha.-oxyimino group in the 7-acetamido moiety and a sulfosubstituted tetrazolylthiomethyl group at position 3. The compounds are active antibacterial agents especially against Gram negative organisms.

  描述了一种新的半合成头孢菌素，其结构特点是在7-乙酰胺基团中具有α-氧亚胺基团，并在位置3处具有磺代取代的四唑硫甲基基团。这些化合物是活性抗菌剂，特别对抗革兰氏阴性菌。
• Cephalosporin derivatives
  申请人：Pfizer Inc.

  公开号：US04080451A1

  公开（公告）日：1978-03-21

  A series of novel 7-(D.alpha.-aminophenylacetamido)- and 7-(D-.alpha.-hydroxyphenylacetamido)- .DELTA..sup.3 -cephem derivatives have been prepared wherein a heterocyclic thiomethyl moiety is located at the 3-position of the molecule. These compounds are useful as antibacterial agents for the treatment of diseases caused by Gram-positive and Gram-negative bacteria. Preferred members include 7-(D-.alpha.-hydroxyphenylacetamido)-3-(3-carbamoyl-1,2,4-triazol-5-yl)thi omethylceph-3-em-4-carboxylic acid and 7-(D-.alpha.-hydroxyphenylacetamido)-3-(2-carboxymethoxy-methyl-1,3,4-thia diazol-5-yl)thiomethylceph-3-em-4-carboxylic acid. Alternative methods of preparation are provided for these compounds, including various synthetic routes leading to the required novel heterocyclic thiol intermediates.

  已制备了一系列新型7-(D.α.-氨基苯乙酰胺基)-和7-(D.α.-羟基苯乙酰胺基)-Δ3-头孢菌素衍生物，其中杂环硫甲基基团位于分子的3位。这些化合物可用作抗菌剂，用于治疗由革兰氏阳性和革兰氏阴性细菌引起的疾病。首选成员包括7-(D.α.-羟基苯乙酰胺基)-3-(3-氨基甲酰-1,2,4-三唑-5-基)硫甲基头孢-3-酮-4-羧酸和7-(D.α.-羟基苯乙酰胺基)-3-(2-羧甲氧甲基-1,3,4-噻二唑-5-基)硫甲基头孢-3-酮-4-羧酸。提供了这些化合物的替代制备方法，包括导致所需新型杂环硫醇中间体的各种合成路线。
• 7-Acyl-3-(sulfoalkyl substituted oxadiazolylthiomethyl) cephalosporins
  申请人：SmithKline Corporation

  公开号：US04041162A1

  公开（公告）日：1977-08-09

  The compounds of this invention are cephalosporins having various acyl substituents at the 7-position and a sulfoalkyl substituted oxadiazolylthiomethyl group at the 3-position of the cephem nucleus and intermediates for the preparation thereof. The 7-acylated compounds have antibacterial activity.

  本发明的化合物是头孢菌素，其在7位具有各种酰基取代基，并且在头孢菌素核心的3位具有磺醇烷基取代的噁二唑硫甲基基团，并提供其制备的中间体。7-酰化化合物具有抗菌活性。
• 7.beta.-Isocyano cephalosporin esters and process of preparation
  申请人：Glaxo Laboratories Limited

  公开号：US03974150A1

  公开（公告）日：1976-08-10

  Novel 6.beta.-isocyano penicillin and 7.beta.-isocyano cephalosporin esters of value as intermediates in the synthesis of penicillin and cephalosporin antibiotics are provided. The novel compounds may be prepared by reaction of the corresponding 6.beta.-formamido penicillin ester or 7.beta.-formamido cephalosporin ester with an acid halide derived from phosphorus, sulphur or carbon or from an oxygen acid of one of said elements, suitable halides including thionyl chloride or phosgene, or with a trivalent phosphorus compound such as triphenylphosphine and a halogenated hydrocarbon such as carbon tetrachloride. The conversion of the novel products to 6.beta.- and 7.beta.- (.alpha.-hydroxy) arylacetamido penicillins and cephalosporins respectively by reaction under acidic conditions with an aromatic aldehyde followed by treatment with an aqueous medium is also described.

  提供了6.beta.-异氰酸基青霉素和7.beta.-异氰酸基头孢菌素酯，作为合成青霉素和头孢菌素抗生素的中间体。这些新化合物可以通过将相应的6.beta.-甲酰胺基青霉素酯或7.beta.-甲酰胺基头孢菌素酯与来自磷、硫或碳的酸卤或来自这些元素之一的氧酸衍生物反应而制备而成，适当的卤化物包括亚磺酰氯或光气，或与三苯基膦等三价磷化合物和卤代烃如四氯化碳反应。还描述了通过在酸性条件下与芳香醛反应，然后用水介质处理，将新产品转化为6.beta.-和7.beta.-(.alpha.-羟基)芳基乙酰胺基青霉素和头孢菌素的方法。
• 3-R-methyl-7-amino-ceph-em-4-carboxylic acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US03932465A1

  公开（公告）日：1976-01-13

  3-R-Methyl-7-amino-ceph-2-em-4.xi.-carboxylic acid compounds, in which R is the C-residue of a C-nucleophilic compound are valuable intermediates, for example, in the manufacture of the corresponding 3-R-methyl-7-amino-ceph-3-em-4-carboxylic acid compounds with antibiotic properties.

  3-R-甲基-7-氨基-头孢-2-乙烯-4.xi.-羧酸化合物，其中R是C-亲核化合物的C-残基，是有价值的中间体，例如，在制造具有抗生素性质的相应的3-R-甲基-7-氨基-头孢-3-乙烯-4-羧酸化合物方面。