3-(2-氯-4-甲基噻唑-5-基)-3-氧代丙酸乙酯 | 1215002-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(2-氯-4-甲基噻唑-5-基)-3-氧代丙酸乙酯
• 英文名称: ethyl 3-(2-chloro-4-methylthiazol-5-yl)-3-oxopropanoate
• 英文别名: Ethyl 3-(2-chloro-4-methyl-1,3-thiazol-5-yl)-3-oxopropanoate
• CAS: 1215002-61-1
• 化学式: C₉H₁₀ClNO₃S
• 分子量: 247.702
• InChiKey: LKMZCAUEQNVTRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.9±50.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-氯-4-甲基噻唑-5-基)-3-氧代丙酸乙酯 、 4-氟苯肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以82%的产率得到1-(4-fluorophenyl)-3-(2-chloro-4-methyl-1,3-thiazo-5-yl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.2174/157018010790596588
• 作为产物：
  描述：

  2-氯-4-甲基-1,3-噻唑-5-甲酸乙酯 、 乙酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以91%的产率得到3-(2-氯-4-甲基噻唑-5-基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.04.008

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。
• 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.