2-(3-chlorophenyl)oxazolo[4,5-b]pyridine | 52333-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-chlorophenyl)oxazolo[4,5-b]pyridine
• 英文别名: 2-(3-chloro-phenyl)-oxazolo[4,5-b]pyridine；2-(3-Chlorphenyl)oxazolo<4,5-b>pyridin；2-(3-chlorophenyl)-[1,3]oxazolo[4,5-b]pyridine
• CAS: 52333-56-9
• 化学式: C₁₂H₇ClN₂O
• 分子量: 230.653
• InChiKey: IZLJFLHRRKXNML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 3-氯苯甲酸 反应 0.05h， 以67%的产率得到2-(3-chlorophenyl)oxazolo[4,5-b]pyridine
  参考文献：
  名称：

  微波辅助直接缩合反应快速制备2-取代的恶唑并[4,5- b ]吡啶

  摘要：

  通过微波辅助加热使2-氨基-3-羟基吡啶与不同的羧酸发生缩合反应是一种以中等到良好的产率制备基于稠合的2-取代的恶唑并[4,5- b ]吡啶的文库的快速方法。

  DOI：

  10.1016/j.tetlet.2007.01.161

文献信息

• 2-(Substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines as nonacidic antiinflammatory agents
  作者：Robert L. Clark、Arsenio A. Pessolano、Bruce Witzel、Thomas Lanza、T. Y. Shen、C. Gordon Van Arman、Edwin A. Risley

  DOI：10.1021/jm00209a014

  日期：1978.11

  Some 2-(substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines have good antiinflammatory and analgesic activity. A few possess activity comparable to phenylbutazone or indomethacin without producing the irritation in the gastrointestinal tract that acidic antiinflammatory compounds cause.

  一些2-（取代的苯基）恶唑并[4,5-b]吡啶和2-（取代的苯基）恶唑并[5,4-b]吡啶具有良好的抗炎和镇痛活性。少数具有与苯基丁a或消炎痛相当的活性，而不会产生酸性抗炎化合物引起的对胃肠道的刺激。
• A rapid method for the preparation of 2-substituted oxazolo[4,5-b]pyridines using microwave-assisted direct condensation reactions
  作者：Mikko J. Myllymäki、Ari M.P. Koskinen

  DOI：10.1016/j.tetlet.2007.01.161

  日期：2007.3

  The condensation reaction of 2-amino-3-hydroxypyridine with different carboxylic acids by microwave-assisted heating is a fast method for producing libraries based on fused 2-substituted oxazolo[4,5-b]pyridines in moderate to good yields.

  通过微波辅助加热使2-氨基-3-羟基吡啶与不同的羧酸发生缩合反应是一种以中等到良好的产率制备基于稠合的2-取代的恶唑并[4,5- b ]吡啶的文库的快速方法。
• Acid-Catalyzed, Silica-Supported, One-Pot Benzoylation Route to Synthesize 2-(Substituted Phenyl)oxazolo[4,5-b]pyridines Under Ambient Conditions
  作者：Gagandeep Kour Reen、Premansh Dudhe、Monika Ahuja、Ashok Kumar、Pratibha Sharma

  DOI：10.1080/00397911.2015.1056797

  日期：2015.9.2

  The present paper describes a silica-supported, perchloric-acid-catalyzed, efficient protocol for the synthesis of 2-(phenyl)oxazolo[4,5-b]pyridine derivatives. This strategy has high conversion, simple workup procedures, ambient conditions, short reaction times, and a reusable catalyst. Structures of the synthesized compounds have been established on the basis of elemental analysis and spectral data (IR, H-1 NMR, C-13 NMR, and mass spectrometry). Moreover, to investigate the mechanistic details of the reaction and to ascertain the regioselective outcome of the product, local nucleophilicity descriptors N-k at B3LYP/6-311G++(d, p) level were determined and analyzed.
• In vitro and in silico evaluation of 2-(substituted phenyl) oxazolo[4,5-b]pyridine derivatives as potential antibacterial agents
  作者：Gagandeep Kour Reen、Ashok Kumar、Pratibha Sharma

  DOI：10.1007/s00044-017-2026-3

  日期：2017.12

  against enterotoxin protein of S. aureus which belongs to Staphylococcal enterotoxin type A(SEA). In vitro and in silico studies revealed that compounds 3d, 3g, and 3h have demonstrated significant antibacterial activity in comparison to the standard control drug ampicillin and streptomycin.

  对抗生素的抗药性增加是世界范围内的主要问题，并刺激了新型细菌抑制剂的发展。我们研究了一系列在我们实验室合成的恶唑并[4,5-b]吡啶，以筛选它们作为潜在的抗菌剂。合成化合物的抗微生物分析基于最小抑菌浓度的测定，针对四种细菌。结果表明，合成的化合物对耐甲氧西林的金黄色葡萄球菌（S. aureus）具有良好的活性，这是造成医院获得性感染的主要细菌。此外，合成的化合物还与金黄色葡萄球菌的肠毒素蛋白对接，该蛋白属于葡萄球菌肠毒素A型（SEA）。体外和计算机模拟研究表明，与标准对照药物氨苄青霉素和链霉素相比，化合物3d，3g和3h具有明显的抗菌活性。