3-(5-氯吡嗪-2-基)-3-氧代丙酸乙酯 | 1215002-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(5-氯吡嗪-2-基)-3-氧代丙酸乙酯
• 英文名称: ethyl 3-(5-chloropyrazin-2-yl)-3-oxopropanoate
• CAS: 1215002-59-7
• 化学式: C₉H₉ClN₂O₃
• 分子量: 228.635
• InChiKey: ZICJSEOITWSXAX-UHFFFAOYSA-N

物化性质

• 沸点：
  329.3±37.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-氯吡嗪-2-基)-3-氧代丙酸乙酯 在 N-碘代丁二酰亚胺 、 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 ethyl 2-bromo-4-(5-chloropyrazin-2-yl)thiazole-5-carboxylate
  参考文献：
  名称：

  Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)

  摘要：

  AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

  DOI：

  10.1021/jm500462x
• 作为产物：
  描述：

  丙二酸单乙酯 、 5-氯吡嗪-2-甲酰氯 在 甲基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-(5-氯吡嗪-2-基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  [EN] 2- (PIPERIDIN-1-YL) -4-HETEROCYCLYL-THIAZOLE-5-CARBOXYLIC ACID DERIVATIVES AGAINST BACTERIAL INFECTIONS
  [FR] DÉRIVÉS DE L'ACIDE 2-(PIPÉRIDINE-1-YL)-4-HÉTÉROCYCLYL-THIAZOLE-5-CARBOXYLIQUE UTILISÉS POUR LUTTER CONTRE LES INFECTIONS BACTÉRIENNES

  摘要：

  化合物的结构式（I）及其药用盐已经描述。还描述了它们的制备方法、含有它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染中的用途。环A从式（a）、（b）或（b'）中选择。

  公开号：

  WO2010067123A1

文献信息

• DPPH Scavenging Assay of Novel 1,3-disubstituted-1H-pyrazol-5-ols and their in silico Studies on Some Proteins Involved in Alzheimers Disease Signaling Cascade
  作者：Balladka Sarojini、Marakkur Vidyagayatri、Chenna Darshanraj、Basavapattana Bharath、Hanumanthappa Manjunatha

  DOI：10.2174/157018010790596588

  日期：2010.3.1

  A series of new 1,3-disubstituted-1H-pyrazol-5-ols (3) which are the analogues of known radical scavenger ‘edaravone’ are synthesized, characterized and evaluated for DPPH scavenging capacity. The docking studies are carried out for these compounds in the enol form and also in the respective keto form against the proteins and peptides involved in Alzhemier disease signal cascade. Some of them showed good radical scavenging capacity and molecular binding.

  本研究合成了一系列新的 1,3-二取代-1H-吡唑-5-醇 (3)，它们是已知自由基清除剂 "依达拉奉 "的类似物，并对其进行了表征和 DPPH 清除能力评估。对这些烯醇形式和酮形式的化合物与阿尔茨海默病信号级联中涉及的蛋白质和肽进行了对接研究。其中一些化合物显示出良好的自由基清除能力和分子结合力。
• Piperidine compounds for use in the treatment of bacterial infections
  申请人：AstraZeneca AB

  公开号：US08071605B2

  公开（公告）日：2011-12-06

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  本文描述了公式(I)的化合物及其药学上可接受的盐。同时还描述了它们的制备过程、含有它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染中的应用。
• PIPERIDINE COMPOUNDS AND USES THEREOF - 596
  申请人：BASARAB Gregory

  公开号：US20100173909A1

  公开（公告）日：2010-07-08

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  本文描述了化学式(I)的化合物及其药学上可接受的盐。同时还描述了它们的制备方法、含有它们的药物组合物、作为药物的用途以及在治疗细菌感染方面的用途。
• 2-(PIPERIDIN-1-YL)-4-HETEROCYCLYL-THIAZOLE-5-CARBOXYLIC ACID DERIVATIVES AGAINST BACTERIAL INFECTIONS
  申请人：BASARAB Gregory

  公开号：US20120028979A1

  公开（公告）日：2012-02-02

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  本文描述了公式(I)的化合物及其药学上可接受的盐。还描述了制备它们的过程、包含它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染中的应用。
• Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines
  作者：R. Venkat Ragavan、V. Vijayakumar、K. Rajesh、B. Palakshi Reddy、S. Karthikeyan、N. Suchetha Kumari

  DOI：10.1016/j.bmcl.2012.04.008

  日期：2012.6

  A series of beta-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 degrees C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these beta-keto esters were characterized using H-1 NMR, C-13 NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity. (C) 2012 Elsevier Ltd. All rights reserved.