2-(2-chloro-6-fluorophenyl)-3-(5-bromo-4,6-dimethylpyrimidin-2-yl)thiazolidin-4-one | 1171120-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2-chloro-6-fluorophenyl)-3-(5-bromo-4,6-dimethylpyrimidin-2-yl)thiazolidin-4-one
• 英文别名: 3-(5-bromo-4,6-dimethylpyrimidin-2-yl)-2-(2-chloro-6-fluorophenyl)-1,3-thiazolidin-4-one
• CAS: 1171120-33-4
• 化学式: C₁₅H₁₂BrClFN₃OS
• 分子量: 416.701
• InChiKey: YAMINYIBKLJXNV-UHFFFAOYSA-N

物化性质

• 熔点：
  153.5-155.0 °C
• 沸点：
  527.3±60.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-5-溴-4,6-二甲基嘧啶 、 2-氯-6-氟-苯甲醛 、 巯基乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以70.9%的产率得到2-(2-chloro-6-fluorophenyl)-3-(5-bromo-4,6-dimethylpyrimidin-2-yl)thiazolidin-4-one
  参考文献：
  名称：

  Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones

  摘要：

  A series of novel thiazolidin-4-ones bearing a hydrophobic substituent at 5-position on the 4,6-dimethyl-pyrimidine ring at N-3 (5c-i and 6c-i) were designed on the prediction of QSAR studies, synthesized in good yields of 60.1-85.3% by microwave-assisted one-pot protocol with the combination of using dicyclohexylcarbonimide (DCC) as the promotor, and evaluated as HIV-1 reverse transcriptases inhibitors. The results of in vitro HIV-1 RT kit assay showed that some of the new compounds, such as 5c, 6c, 5d, 6d, 5g, 5h and 6i, could effectively inhibit RT activity. Among them, compounds 5c and 6c where ethyl group existed at 5-position on N-3 pyrimidine ring were the best ones with the IC50 value of 0.26 mu M and 0.23 mu M, respectively. Structure-activity relationship analysis of these analogues suggested that the overall hydrophobicity and steric factor were important to the anti-HIV RT activity. The mechanism of the intramolecular cycloamidation promoted by DCC was also investigated with the key uncyclized intermediate 13. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.024

文献信息

• Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones
  作者：Hua Chen、Jie Bai、Lingling Jiao、Zaihong Guo、Qingmei Yin、Xiaoliu Li

  DOI：10.1016/j.bmc.2009.04.024

  日期：2009.6

  A series of novel thiazolidin-4-ones bearing a hydrophobic substituent at 5-position on the 4,6-dimethyl-pyrimidine ring at N-3 (5c-i and 6c-i) were designed on the prediction of QSAR studies, synthesized in good yields of 60.1-85.3% by microwave-assisted one-pot protocol with the combination of using dicyclohexylcarbonimide (DCC) as the promotor, and evaluated as HIV-1 reverse transcriptases inhibitors. The results of in vitro HIV-1 RT kit assay showed that some of the new compounds, such as 5c, 6c, 5d, 6d, 5g, 5h and 6i, could effectively inhibit RT activity. Among them, compounds 5c and 6c where ethyl group existed at 5-position on N-3 pyrimidine ring were the best ones with the IC50 value of 0.26 mu M and 0.23 mu M, respectively. Structure-activity relationship analysis of these analogues suggested that the overall hydrophobicity and steric factor were important to the anti-HIV RT activity. The mechanism of the intramolecular cycloamidation promoted by DCC was also investigated with the key uncyclized intermediate 13. (C) 2009 Elsevier Ltd. All rights reserved.