ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate | 181058-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 181058-43-5
• 化学式: C₁₆H₁₅ClN₂O₃S
• 分子量: 350.826
• InChiKey: JOYDAFNQZNEJSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 Ethyl 4-amino-6-(2-chlorophenyl)-13-(4-chlorophenyl)-5-cyano-11-methyl-3-oxa-8-thia-1,10-diazatricyclo[7.4.0.02,7]trideca-2(7),4,9,11-tetraene-12-carboxylate
  参考文献：
  名称：

  SYNTHESIS AND RADIATION STABILITY OF NOVEL THIAZOLOPYRIMIDINES WITH EXPECTED ANTIFUNGAL ACTIVITY

  摘要：

  A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4'-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and me structures are stable.

  DOI：

  10.1080/10426509608029657
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 cerium(III) chloride heptahydrate 、 sodium acetate 作用下， 以 乙醇 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 11.0h， 生成 ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase

  摘要：

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.096

文献信息

• An Efficient Synthesis of Some Novel Bicyclic Thiazolopyrimidine Derivatives
  作者：Akbar Mobinikhaledi、Mojgan Zendehdel、Mahdia Hamidi Nasab、Mohammad Ali Bodaghi Fard

  DOI：10.1515/hc.2009.15.6.451

  日期：2009.1

  An efficient and rapid synthesis of some thiazolopyrimidine derivatives from pyrimidinthiones and chloroacetyl chloride in refluxing tetrahydrofurane (THF) is described. The method is simple and practical, and generating thiazole derivatives in good isolated yields.

  描述了在回流四氢呋喃 (THF) 中由嘧啶硫酮和氯乙酰氯高效快速合成一些噻唑并嘧啶衍生物。该方法简单实用，生成的噻唑衍生物分离收率良好。
• Pathak, Arun; Narayanaswamy, Venugopala Katharigatta; Joshi, Aakanksha, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 273 - 276
  作者：Pathak, Arun、Narayanaswamy, Venugopala Katharigatta、Joshi, Aakanksha、Rao, Gopal Krishna、Devi, Kalpana

  DOI：——

  日期：——
• Synthesis Of Novel 5-Methylindeno[2,1E][1,3]Thiazolo[3,2-A]Pyrimidine-1,6(2H,10bH)-Diones
  作者：Akbar Mobinikhaledi、Amir Jafari

  DOI：10.1515/hc.2009.15.5.351

  日期：2009.1

  Treatment of ethyl 5-aryl-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 1(a-h), with aluminum chloride and acetyl chloride in nitrobenzene gave the corresponding 5-Methylindeno[2,1-e][1,3]thiazolo[3,2-a]pyrimidine-1,6(2H,10bH)-dione derivatives 2(a-h). Yields of the products, after recrystallizing with acetic acid, were of the order of 46-67%. H-1-NMR and C-13-NMR spectroscopy, and elemental analysis were used for identification of these compounds.
• Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase
  作者：Dan Zhao、Chen Chen、Huayong Liu、Likang Zheng、Yao Tong、Di Qu、Shiqing Han

  DOI：10.1016/j.ejmech.2014.09.096

  日期：2014.11

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.
• SYNTHESIS AND RADIATION STABILITY OF NOVEL THIAZOLOPYRIMIDINES WITH EXPECTED ANTIFUNGAL ACTIVITY
  作者：M. M. Ghorab、Y. A. Mohamed、S. A. Mohamed、Y. A. Ammar

  DOI：10.1080/10426509608029657

  日期：1996.1.1

  A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4'-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and me structures are stable.