7-β-<2-(thien-2-yl)acetamido>-3-hydroxymethyl-2-cephem-4-carboxylic acid | 30200-18-1

• 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
• 英文名称: 7-β-<2-(thien-2-yl)acetamido>-3-hydroxymethyl-2-cephem-4-carboxylic acid
• 英文别名: 7β-(2-(thien-2-yl)acetamido)-3-(hydroxymethyl)-2-cephem-4-carboxylic acid；7β-[2-(thien-2-yl)acetamido]-3-(hydroxymethyl)-2-cephem-4-carboxylic acid；3-Hydroxymethyl-7beta-(2-thienylacetamido)ceph-2-em-4-carboxylic acid；(6R,7R)-3-(hydroxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• CAS: 30200-18-1
• 化学式: C₁₄H₁₄N₂O₅S₂
• 分子量: 354.408
• InChiKey: WNFUAKIFLZQTSP-IAUSTGCCSA-N

物化性质

• 沸点：
  800.7±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  161
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-β-<2-(thien-2-yl)acetamido>-3-hydroxymethyl-2-cephem-4-carboxylic acid 在 四(三苯基膦)钯 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 焦磷酸硫胺素 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-carboxyl-5-sulfoxide-7-(2-thienyl)acetamido-2-cephem-3-methyl 3-(2-chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

  摘要：

  Dual-action agents 5a-f and 12a-f. a beta-lactam antibiotic combined with a cytotoxic agent. mitozolomide (Meto) or temozolomide (Temo). were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several beta-lactamase producing strains. The tests showed 5a-f active against the non-p-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains. however, little synergistic effect between the P-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a. in particular. is active against ampicillin resistant (beta-lactamase-producing) strains of Serratia marcescens. (C) 2002 Published by editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01331-9
• 作为产物：
  描述：

  头孢噻吩 在 吡啶 、 盐酸 、 sodium hydroxide 、 乙酸酐 作用下， 以 水 为溶剂， 生成 7-β-<2-(thien-2-yl)acetamido>-3-hydroxymethyl-2-cephem-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

  摘要：

  Dual-action agents 5a-f and 12a-f. a beta-lactam antibiotic combined with a cytotoxic agent. mitozolomide (Meto) or temozolomide (Temo). were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several beta-lactamase producing strains. The tests showed 5a-f active against the non-p-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains. however, little synergistic effect between the P-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a. in particular. is active against ampicillin resistant (beta-lactamase-producing) strains of Serratia marcescens. (C) 2002 Published by editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01331-9

文献信息

• .DELTA..sup.3 -3-Vinyl or substituted vinyl-4-carboxy cephalosporins
  申请人：Glaxo Laboratories Limited

  公开号：US04107431A1

  公开（公告）日：1978-08-15

  The invention is concerned with .DELTA..sup.3 -4-carboxy cephalosporin antibiotics possessing a 3-vinyl or substituted 3-vinyl groups as well as with phosphorous intermediates useful in the preparation thereof.

  这项发明涉及具有3-乙烯基或取代3-乙烯基团的.DELTA..sup.3-4-羧基头孢菌素抗生素，以及用于制备其的磷中间体。
• Process for the preparation of 3-vinyl and substituted vinyl
  申请人：Glaxo Laboratories Limited

  公开号：US04110534A1

  公开（公告）日：1978-08-29

  The invention is concerned with the preparation of .DELTA..sup.3 -4-carboxy cephalosporin antibiotics possessing a 3-vinyl group or substituted 3-vinyl group by means of phosphorous intermediates.

  本发明涉及使用磷中间体制备具有3-乙烯基或取代3-乙烯基的.DELTA..sup.3 -4-羧基头孢菌素类抗生素。
• Delivery of cytotoxic agents
  申请人：ELI LILLY AND COMPANY

  公开号：EP0382411A2

  公开（公告）日：1990-08-16

  Provided is a means for delivery of a cytotoxic agent which is useful in the treatment of neoplastic diseases. In particular, Antibody-Enzyme Conjugates and Substrate-Cytotoxic Agent compounds are disclosed.

  本文提供了一种用于治疗肿瘤性疾病的细胞毒剂的输送方法。特别是，公开了抗体-酶结合物和底物-细胞毒剂化合物。
• Synthesis of acylhydrazido-substituted cephems. Design of cephalosporin-vinca alkaloid prodrugs: substrates for an antibody targeted enzyme
  作者：Louis N. Jungheim、Timothy A. Shepherd、Damon L. Meyer

  DOI：10.1021/jo00034a027

  日期：1992.4

  Cephalosporin 20 substituted at the C-3' position with the potent oncolytic agent desacetylvinblastine hydrazide (3) was synthesized as a potential prodrug for the treatment of solid tumors. The design of this novel prodrug was based on the knowledge that hydrolysis of a cephalosporin's beta-lactam bond can result in the expulsion of the C-3' substituent. Proper selection of the linkage used to join the cephem to the vinca, e.g., 8 vs 20, provided a releasable form of the drug as well as a chemically stable prodrug. We envisioned the conversion of prodrug to free vinca to be mediated by an immunoconjugate, consisting of a beta-lactamase enzyme covalently attached to a monoclonal antibody, which has been prelocalized at the tumor. Treatment of candidate prodrugs with the P99 beta-lactamase enzyme isolated from Enterobacter cloacae 265A efficiently catalyzed their conversion to the free drug form. A study of model compounds 11 and 18 indicated that cephem 1-beta-sulfoxide 18 was a better substrate for the enzyme than its sulfide counterpart 11. This finding prompted the synthesis of cephem sulfoxide 20 which was efficiently accomplished via condensation of desacetylvinblastine hydrazide with the cephalothin derived cephem 3'-p-nitrophenyl carbonate 15.
• Jungheim, Louis N.; Shepherd, Timothy A.; Kling, James K., Heterocycles, 1993, vol. 35, # 1, p. 339 - 348
  作者：Jungheim, Louis N.、Shepherd, Timothy A.、Kling, James K.

  DOI：——

  日期：——