2,4-dichloro-6-(4-isopropylanilino)-s-triazine | 146887-22-1

• 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: 2,4-dichloro-6-(4-isopropylanilino)-s-triazine
• 英文别名: (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-isopropyl-phenyl)-amine；4,6-dichloro-N-(4-propan-2-ylphenyl)-1,3,5-triazin-2-amine
• CAS: 146887-22-1
• 化学式: C₁₂H₁₂Cl₂N₄
• mdl: MFCD01543148
• 分子量: 283.16
• InChiKey: HZIYJENFXOPSFC-UHFFFAOYSA-N

物化性质

• 沸点：
  447.3±38.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)
• 溶解度：
  28.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,4-dichloro-6-(4-isopropylanilino)-s-triazine 、 (S)-2-巯基-2-苯基乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到Methyl 2-[[4-chloro-6-(4-propan-2-ylanilino)-1,3,5-triazin-2-yl]sulfanyl]-2-phenylacetate
  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-异丙基苯胺 以 丙酮 为溶剂， 反应 1.0h， 以87%的产率得到2,4-dichloro-6-(4-isopropylanilino)-s-triazine
  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

• <i>In Vitro</i>Evaluation of<i>s</i>-Triazine Derivatives for African Trypanosomiasis
  作者：Jae Ho Jin、Eun Beul Park、Kwang Jong Kim、Minju Kim、Sunhoe Lee、Kyung-Tae Lee、Gyongseon Yang、Soo Young Byun、Nakyung Lee、Junghyun Goo、Joo Hwan No、Dong Joon Choo、Jae Yeol Lee

  DOI：10.1002/bkcs.10447

  日期：2015.9
• DEFAUNATION METHOD
  申请人：MALLINCKRODT VETERINARY LIMITED

  公开号：EP0661976A1

  公开（公告）日：1995-07-12
• EP0661976A4
  申请人：——

  公开号：EP0661976A4

  公开（公告）日：1994-07-20
• US5561131A
  申请人：——

  公开号：US5561131A

  公开（公告）日：1996-10-01
• [EN] DEFAUNATION METHOD
  申请人：PITMAN-MOORE AUSTRALIA LIMITED

  公开号：WO1993002680A1

  公开（公告）日：1993-02-18

  (EN) The use of triazine compounds of formula (I) for the preparation of a medicament for use in a method for defaunation of ruminant animals, in which an effective amount of the compound is administered to the animals. Defaunation is the selective removal of protozoa from the rumen in preference to removal or deactivation of bacteria. In formula (I): x = 1 or 2, R = H or lower alkyl, Ar = phenyl, diphenyl, naphthyl, anthracyl or phenanthryl radicals and substituted derivatives thereof.(FR) Utilisation de composés de triazine de la formule (I) pour la préparation d'un médicament utilisé dans un procédé de défaunation de ruminants, selon lequel une quantité efficace du composé est administrée aux animaux. La défaunation consiste à enlever de préférence sélectivement des protozoaires de la panse au lieu d'enlever ou de désactiver des bactéries. Dans la formule (I) x = 1 ou 2, R = H ou alkyle inférieur, Ar = radicaux de phényle, diphényle, naphtyle, anthracyle ou phénanthryle et dérivés substitués de ces radicaux.