6-chloro-N²-(5-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-yloxy) pentyl)-N⁴-phenyl-1,3,5-triazine-2,4-diamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-chloro-N²-(5-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-yloxy) pentyl)-N⁴-phenyl-1,3,5-triazine-2,4-diamine
• 英文别名: 4-N-[5-[(4-anilino-6-chloro-1,3,5-triazin-2-yl)oxy]pentyl]-6-chloro-2-N-phenyl-1,3,5-triazine-2,4-diamine
• 化学式: C₂₃H₂₃Cl₂N₉O
• 分子量: 512.401
• InChiKey: BIFARPVMCVMGQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  正丙胺 、 6-chloro-N²-(5-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-yloxy) pentyl)-N⁴-phenyl-1,3,5-triazine-2,4-diamine 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到N²-phenyl-N4-(5-(4-(phenylamino)-6-(propylamino)-1,3,5-triazin-2-yloxy)pentyl)-N⁶-propyl-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Discovery of Triazine Mimetics As Potent Antileishmanial Agents

  摘要：

  The World Health Organization has classified the leishmaniasis as a major tropical disease. The discovery of new compounds for leishmaniasis is therefore a pressing concern for the anti-infective research program. We have synthesized 19 compounds of triazine dimers as novel antileishmanial agents. Most of the synthesized derivatives exhibited better activity against intracellular amastigotes (IC50 ranging from 0.77 to 10.32 mu M) than the control, pentamidine (IC50 = 13.68 mu M), and are not toxic to Vero cells. Compounds 14 and 15 showed significant in vivo inhibition of 74.41% and 62.64%, respectively, in L. donovani/hamster model. Moreover, expansion of Th1-type and suppression of Th2-type immune responses proved that compound 14 stimulates mouse macrophages to prevent the progression of leishmania parasite. The molecular docking studies involving PTR1 protein PDB further validated the concepts involved in the design of these compounds. Among the investigated analogues, compound 14 has emerged as the potential one to enlarge the scope of the study.

  DOI：

  10.1021/ml400317e
• 作为产物：
  描述：

  4,6-二氯-N-苯基-1,3,5-噻嗪-2-胺 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 6-chloro-N²-(5-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-yloxy) pentyl)-N⁴-phenyl-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Discovery of Triazine Mimetics As Potent Antileishmanial Agents

  摘要：

  The World Health Organization has classified the leishmaniasis as a major tropical disease. The discovery of new compounds for leishmaniasis is therefore a pressing concern for the anti-infective research program. We have synthesized 19 compounds of triazine dimers as novel antileishmanial agents. Most of the synthesized derivatives exhibited better activity against intracellular amastigotes (IC50 ranging from 0.77 to 10.32 mu M) than the control, pentamidine (IC50 = 13.68 mu M), and are not toxic to Vero cells. Compounds 14 and 15 showed significant in vivo inhibition of 74.41% and 62.64%, respectively, in L. donovani/hamster model. Moreover, expansion of Th1-type and suppression of Th2-type immune responses proved that compound 14 stimulates mouse macrophages to prevent the progression of leishmania parasite. The molecular docking studies involving PTR1 protein PDB further validated the concepts involved in the design of these compounds. Among the investigated analogues, compound 14 has emerged as the potential one to enlarge the scope of the study.

  DOI：

  10.1021/ml400317e