2,4-dichloro-6-(3,5-dimethylpiperidin-1-yl)-1,3,5-triazine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,4-dichloro-6-(3,5-dimethylpiperidin-1-yl)-1,3,5-triazine
• 化学式: C₁₀H₁₄Cl₂N₄
• 分子量: 261.154
• InChiKey: ZPRNZUQGDCVKPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲基哌啶 、 2,4-dichloro-6-(3,5-dimethylpiperidin-1-yl)-1,3,5-triazine 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以85%的产率得到2-chloro-4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazine
  参考文献：
  名称：

  Synthesis of potential antitubercular and antimicrobial s-triazine-based scaffolds via Suzuki cross-coupling reaction

  摘要：

  Two series of bis(3,5-dimethylpiperidinyl)-1,3,5-triazinyl)-N-(phenyl/benzothiazolyl)-acetamides were synthesized so as to investigate their antimicrobial and antimycobacterial actions. Intermediate 4-(4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazin-2-yl)aniline was synthesized by palladium-catalyzed Suzuki cross-coupling reaction to furnish C-C bond formation to s-triazine ring. Pharmacological screening against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri), four fungi (A. niger, A. fumigatus, A. clavatus, and C. albicans), and Mycobacterium tuberculosis H37Rv was examined and the effects of various substituents on biological profiles (MIC, 1.56-50 mu g/mL) of final analogues were investigated. Four (8c, 8i, 9d, 9j) of the final analogues displayed antimycobacterial activity (3.12-6.25 mu g/mL) equipotent to standard drugs.

  DOI：

  10.1007/s00044-012-0041-y
• 作为产物：
  描述：

  3,5-二甲基哌啶 、 氰尿酸 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以87%的产率得到2,4-dichloro-6-(3,5-dimethylpiperidin-1-yl)-1,3,5-triazine
  参考文献：
  名称：

  Synthesis of potential antitubercular and antimicrobial s-triazine-based scaffolds via Suzuki cross-coupling reaction

  摘要：

  Two series of bis(3,5-dimethylpiperidinyl)-1,3,5-triazinyl)-N-(phenyl/benzothiazolyl)-acetamides were synthesized so as to investigate their antimicrobial and antimycobacterial actions. Intermediate 4-(4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazin-2-yl)aniline was synthesized by palladium-catalyzed Suzuki cross-coupling reaction to furnish C-C bond formation to s-triazine ring. Pharmacological screening against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri), four fungi (A. niger, A. fumigatus, A. clavatus, and C. albicans), and Mycobacterium tuberculosis H37Rv was examined and the effects of various substituents on biological profiles (MIC, 1.56-50 mu g/mL) of final analogues were investigated. Four (8c, 8i, 9d, 9j) of the final analogues displayed antimycobacterial activity (3.12-6.25 mu g/mL) equipotent to standard drugs.

  DOI：

  10.1007/s00044-012-0041-y

文献信息

• Design, synthesis and anti-cancer evaluation of genistein-1,3,5-triazine derivatives
  作者：Jing-Pei Zou、Zhen Zhang、Jin-Yu Lv、Xiao-Qing Zhang、Zhao-Yuan Zhang、Shu-Tong Han、Yu-Wei Liu、Wei-Wei Liu、Jing Ji、Da-Hua Shi

  DOI：10.1016/j.tet.2023.133293

  日期：2023.3

  MTT assay. Most genistein-1,3,5-triazine derivatives showed better anti-cancer activity than nuclear parent genistein. Compound 4i displayed the strongest antiproliferative activity against MDA-MB-231 cells (IC50 = 23.13 μM), which was better than 5-fluorouracil (IC50 = 78.04 μM). Further studies showed that compound 4i not only could inhibit the migration, invasion and adhesion of MDA-MB-231 cells, but

  通过亲核取代合成了12个染料木黄酮-1,3,5-三嗪衍生物，并通过1 H NMR、13 C NMR、IR、HR-MS和单晶X射线衍射对其进行了表征。HPLC测定目标化合物纯度在99%以上。这些化合物对 MDA-MB-231（乳腺癌）、HeLa（宫颈癌）、HCT-116（前列腺癌）和 Huh-7（肝癌）癌细胞系的抗增殖活性通过 MTT 测定法进行评估。大多数染料木黄酮-1,3,5-三嗪衍生物显示出比核母体染料木黄酮更好的抗癌活性。化合物4i对 MDA-MB-231 细胞显示出最强的抗增殖活性 (IC 50  = 23.13 μM)，优于 5-氟尿嘧啶 (IC 50 = 78.04 μM）。进一步研究表明，化合物4i不仅可以抑制MDA-MB-231细胞的迁移、侵袭和粘附，而且对体内MDA-MB-231肿瘤异种移植物的增殖也有很大的抑制作用。此外，ADME 特性和毒性预测表明这些化合物可能具有成
• Synthesis of potential antitubercular and antimicrobial s-triazine-based scaffolds via Suzuki cross-coupling reaction
  作者：Amit B. Patel、Rahul V. Patel、Premlata Kumari、Dhanji P. Rajani、Kishor H. Chikhalia

  DOI：10.1007/s00044-012-0041-y

  日期：2013.1

  Two series of bis(3,5-dimethylpiperidinyl)-1,3,5-triazinyl)-N-(phenyl/benzothiazolyl)-acetamides were synthesized so as to investigate their antimicrobial and antimycobacterial actions. Intermediate 4-(4,6-bis(3,5-dimethylpiperidin-1-yl)-1,3,5-triazin-2-yl)aniline was synthesized by palladium-catalyzed Suzuki cross-coupling reaction to furnish C-C bond formation to s-triazine ring. Pharmacological screening against eight bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, and S. flexneri), four fungi (A. niger, A. fumigatus, A. clavatus, and C. albicans), and Mycobacterium tuberculosis H37Rv was examined and the effects of various substituents on biological profiles (MIC, 1.56-50 mu g/mL) of final analogues were investigated. Four (8c, 8i, 9d, 9j) of the final analogues displayed antimycobacterial activity (3.12-6.25 mu g/mL) equipotent to standard drugs.