ethyl 2-(2-aminothiazol-4-yl)-2-((tert-butoxycarbonyl)amino)acetate | 60846-29-9

• 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: ethyl 2-(2-aminothiazol-4-yl)-2-((tert-butoxycarbonyl)amino)acetate
• 英文别名: alpha-t-Butyloxycarbonylamino-alpha-(2-aminothiazol-4-yl)acetic acid ethyl ester；ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 60846-29-9
• 化学式: C₁₂H₁₉N₃O₄S
• 分子量: 301.367
• InChiKey: DLVPELUHTUSYMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  471.5±40.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-aminothiazol-4-yl)-2-((tert-butoxycarbonyl)amino)acetate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.33h， 生成 (2-Allyloxycarbonylamino-thiazol-4-yl)-amino-acetic acid ethyl ester
  参考文献：
  名称：

  Antimicrobial effects of novel siderophores linked to β-lactam antibiotics

  摘要：

  As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-P-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00261-8
• 作为产物：
  描述：

  2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid-S-ethyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 ethyl 2-(2-aminothiazol-4-yl)-2-((tert-butoxycarbonyl)amino)acetate
  参考文献：
  名称：

  Hardy, Kenneth D.; Harrington, Frank P.; Stachulski, Andrew V., Journal of the Chemical Society. Perkin transactions I, 1984, # 6, p. 1227 - 1236

  摘要：

  DOI：

文献信息

• [EN] PENICILLIN-BINDING PROTEIN INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINE DE LIAISON À LA PÉNICILLINE
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2019226931A1

  公开（公告）日：2019-11-28

  Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.

  本文描述了某些含硼化合物、组合物、制剂及其作为细菌青霉素结合蛋白的跨肽酶功能调节剂和抗菌剂的用途。在某些实施例中，本文描述的化合物抑制青霉素结合蛋白。在某些实施例中，本文描述的化合物在治疗细菌感染方面是有用的。
• [EN] PENICILLIN-BINDING PROTEIN INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINES DE LIAISON À LA PÉNICILLINE
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2018218190A1

  公开（公告）日：2018-11-29

  Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.

  本文描述了某些含硼化合物、组合物、制剂及它们作为细菌青霉素结合蛋白的跨肽酶功能调节剂和抗菌剂的用途。在某些实施例中，本文描述的化合物抑制青霉素结合蛋白。在某些实施例中，本文描述的化合物在治疗细菌感染方面是有用的。
• Thiazolylacetamido cephalosporin type compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04098888A1

  公开（公告）日：1978-07-04

  Novel cephem compounds of the formula; ##STR1## wherein R.sup.1 represents amino or hydroxyl group which may be protected, R.sup.2 represents amino or hydroxyl group or a group convertible into these groups, R.sup.3 represents hydrogen or methoxy group or a group convertible into methoxy group, R.sup.4 represents hydrogen or a residue of a nucleophilic compound and R.sup.8 represents hydrogen or a halogen, or a pharmaceutically acceptable salt or ester thereof, have strong antibiotic properties against a wide variety of microorganisms including gram-positive bacteria as well as gram-negative ones, especially by oral administration and can be used as therapeutic agent for various bacterial infections of animals including human beings.

  新型头孢菌素化合物的化学式如下；##STR1## 其中R.sup.1代表氨基或羟基，可以被保护，R.sup.2代表氨基或羟基或可转化为这些基团的基团，R.sup.3代表氢或甲氧基或可转化为甲氧基的基团，R.sup.4代表氢或亲核化合物的残基，R.sup.8代表氢或卤素，或其药用可接受的盐或酯，具有强大的抗生素特性，对包括革兰氏阳性细菌和革兰氏阴性细菌在内的各种微生物具有抗性，特别是经口服给药，可用作动物包括人类的各种细菌感染的治疗剂。
• Thiazolylacetamido cephalosporin compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04668783A1

  公开（公告）日：1987-05-26

  Novel cephem compounds of the formula: ##STR1## wherein R.sup.4 is a residue of a nucleophilic compound selected from hydroxyl, mercapto, cyano, azido, amino, carbamoyloxy, carbamoylthio and thiocarbamoyloxy, said group being unsubstituted or substituted by alkyl of up to three carbons, and R.sup.5 is hydroxyl or lower alkoxy, or a pharmaceutically acceptable ester thereof, have strong antibiotic properties against a wide variety of microorganisms.

  公式为：##STR1## 其中R.sup.4是亲核化合物的残基，所述亲核化合物选自羟基、巯基、氰基、偶氮基、氨基、氨基甲酰氧基、氨基甲硫氧基和硫代氨基甲酰氧基，该基团未被取代或被烷基取代，烷基的碳数不超过3；R.sup.5是羟基或较低的烷氧基，或其药学上可接受的酯，对各种微生物具有强大的抗生素作用。
• Cephem compounds
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04912212A1

  公开（公告）日：1990-03-27

  Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein -W-R is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl, or a pharmaceutically acceptable salt or 4-carboxy ester which is the alkoxymethyl, .alpha.-alkoxyethyl, .alpha.-alkoxy-.alpha.-substituted methyl, alkylthiomethyl, acyloxymethyl or .alpha.-acyloxy-.alpha.-substituted methyl ester thereof.

  提供广谱抗生素，其为以下式子的化合物：##STR1## 其中-W-R为亲核化合物的残基，R.sup.5为羟基或保护羟基，或者是药学上可接受的盐或4-羧基酯，其为其烷氧甲基、α-烷氧乙基、α-烷氧-α-取代甲基、烷基硫甲基、酰氧甲基或α-酰氧-α-取代甲基酯。