N2-(4-cyclohexylphenyl)-4,6-dichloro-1,3,5-triazin-2-amine

• 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: N2-(4-cyclohexylphenyl)-4,6-dichloro-1,3,5-triazin-2-amine
• 英文别名: 4,6-dichloro-N-(4-cyclohexylphenyl)-1,3,5-triazin-2-amine
• 化学式: C₁₅H₁₆Cl₂N₄
• 分子量: 323.225
• InChiKey: ZCOWQNHBEZKPJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 N2-(4-cyclohexylphenyl)-4,6-dichloro-1,3,5-triazin-2-amine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到Ethyl 2-[[4-chloro-6-(4-cyclohexylanilino)-1,3,5-triazin-2-yl]sulfanyl]-2-naphthalen-1-ylacetate
  参考文献：
  名称：

  Synthesis and PGE2 production inhibition of s-triazine derivatives as a novel scaffold in RAW 264.7 macrophage cells

  摘要：

  We present the synthesis and biological evaluation of a collection of s-triazine derivatives as a novel scaffold of compounds with the capability to inhibit the PGE(2) production in LPS-induced RAW 264.7 macrophage cells. A total of 12 derivatives were synthesized and assayed for PGE(2) reduction at 10 mu M concentration. Two compounds (7b and 7i) exhibiting >90% inhibition of PGE(2) production were found to have IC50 values of 5.76 and 5.52 mu M, respectively. They were counter screened for inhibition on COX-2 activity in a cell free assay. Specifically, compound 7i (R-1 = 4-Bn-Ph, R-2 = Cl, R-3 = Ph, R-5 = CO2Me) was highly active in cells while maintaining little COX-2 inhibition (similar to 0% at 10 mu M). Molecular docking study provides the possibility that compound 7i could inhibit PGE(2) production by blocking the PGH(2) binding site of mPGES-1 instead of COX-2 enzyme. Based on this result, our synthetic efforts will focus on intensive structure-activity relationship (SAR) study of s-triazine scaffold to discovery a potential PGE(2) synthesis inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.031
• 作为产物：
  描述：

  三聚氯氰 、 4-环己苯胺 以 丙酮 为溶剂， 反应 1.0h， 以92%的产率得到N2-(4-cyclohexylphenyl)-4,6-dichloro-1,3,5-triazin-2-amine
  参考文献：
  名称：

  Synthesis and PGE2 production inhibition of s-triazine derivatives as a novel scaffold in RAW 264.7 macrophage cells

  摘要：

  We present the synthesis and biological evaluation of a collection of s-triazine derivatives as a novel scaffold of compounds with the capability to inhibit the PGE(2) production in LPS-induced RAW 264.7 macrophage cells. A total of 12 derivatives were synthesized and assayed for PGE(2) reduction at 10 mu M concentration. Two compounds (7b and 7i) exhibiting >90% inhibition of PGE(2) production were found to have IC50 values of 5.76 and 5.52 mu M, respectively. They were counter screened for inhibition on COX-2 activity in a cell free assay. Specifically, compound 7i (R-1 = 4-Bn-Ph, R-2 = Cl, R-3 = Ph, R-5 = CO2Me) was highly active in cells while maintaining little COX-2 inhibition (similar to 0% at 10 mu M). Molecular docking study provides the possibility that compound 7i could inhibit PGE(2) production by blocking the PGH(2) binding site of mPGES-1 instead of COX-2 enzyme. Based on this result, our synthetic efforts will focus on intensive structure-activity relationship (SAR) study of s-triazine scaffold to discovery a potential PGE(2) synthesis inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.031

文献信息

• Synthesis and PGE2 production inhibition of s-triazine derivatives as a novel scaffold in RAW 264.7 macrophage cells
  作者：Seoung Mook Kang、Jinsung Lee、Jae Ho Jin、Minju Kim、Sunhoe Lee、Hwi Ho Lee、Ji-Sun Shin、Kyung-Tae Lee、Jae Yeol Lee

  DOI：10.1016/j.bmcl.2014.10.031

  日期：2014.12

  We present the synthesis and biological evaluation of a collection of s-triazine derivatives as a novel scaffold of compounds with the capability to inhibit the PGE(2) production in LPS-induced RAW 264.7 macrophage cells. A total of 12 derivatives were synthesized and assayed for PGE(2) reduction at 10 mu M concentration. Two compounds (7b and 7i) exhibiting >90% inhibition of PGE(2) production were found to have IC50 values of 5.76 and 5.52 mu M, respectively. They were counter screened for inhibition on COX-2 activity in a cell free assay. Specifically, compound 7i (R-1 = 4-Bn-Ph, R-2 = Cl, R-3 = Ph, R-5 = CO2Me) was highly active in cells while maintaining little COX-2 inhibition (similar to 0% at 10 mu M). Molecular docking study provides the possibility that compound 7i could inhibit PGE(2) production by blocking the PGH(2) binding site of mPGES-1 instead of COX-2 enzyme. Based on this result, our synthetic efforts will focus on intensive structure-activity relationship (SAR) study of s-triazine scaffold to discovery a potential PGE(2) synthesis inhibitor. (C) 2014 Elsevier Ltd. All rights reserved.