N-(4-Chlorobenzylidene)-4-methylthioaniline | 3447-45-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-Chlorobenzylidene)-4-methylthioaniline
• 英文别名: 1-(4-chlorophenyl)-N-(4-methylsulfanylphenyl)methanimine
• CAS: 3447-45-8
• 化学式: C₁₄H₁₂ClNS
• 分子量: 261.775
• InChiKey: RDTTVQAYOFLJJC-UHFFFAOYSA-N

物化性质

• 沸点：
  401.4±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-Chlorobenzylidene)-4-methylthioaniline 在 potassium carbonate 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 2-chloro-5-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)imidazole
  参考文献：
  名称：

  Synthesis of Halogenated 1,5-Diarylimidazoles and Their Inhibitory Effects on LPS-Induced PGE2 Production in RAW 264.7 Cells

  摘要：

  一系列卤代的1,5-二芳基咪唑化合物被合成，并评估了它们对RAW 264.7细胞中LPS诱导的PGE2产生的抑制作用。通过两种不同的途径合成了各种2,4-、4-和2-卤代的5-芳基-1-(4-甲基磺酰基苯基)咪唑，用于SAR研究。总体而言，无论卤素的种类如何，4-卤代的5-芳基-1-(4-甲基磺酰基苯基)咪唑都表现出非常强的PGE2产生抑制活性。其中，4-氯-5-(4-甲氧基苯基)-1-(4-甲基磺酰基苯基)咪唑(3，IC50 3.3 nM ± 2.93)和4-氯-5-(4-氯苯基)-1-(4-甲基磺酰基苯基)咪唑(13，IC50 5.3 nM ± 0.23)表现出最佳的结果。

  DOI：

  10.3390/molecules26206093
• 作为产物：
  描述：

  4-氯苯甲醛 、 4-氨基茴香硫醚 以93%的产率得到N-(4-Chlorobenzylidene)-4-methylthioaniline
  参考文献：
  名称：

  1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells

  摘要：

  A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE(2) production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.092

文献信息

• 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic
  申请人：Sankyo Company, Limited

  公开号：US05908858A1

  公开（公告）日：1999-06-01

  Compounds of formula (I) and (II): ##STR1## \x9bwherein R is hydrogen, halogen or alkyl; R.sup.1 is alkyl, amino or substituted amino; R.sup.2 is optionally substituted phenyl; R.sup.3 is hydrogen, halogen or optionally substituted alkyl; R.sup.4 is hydrogen, optionally substituted alkyl, cycloalkyl, aryl, or aralkyl! have valuable analgesic, anti-inflammatory, anti-pyretic and anti-allergic activities and have the ability to inhibit the production of leukotrienes and to inhibit bone resorption. They are relatively free from the side effects which generally result from the administration of compounds having these kinds of activities.

  式(I)和(II)的化合物：##STR1## 其中R为氢、卤素或烷基；R.sup.1为烷基、氨基或取代氨基；R.sup.2为可选取代的苯基；R.sup.3为氢、卤素或可选取代的烷基；R.sup.4为氢、可选取代的烷基、环烷基、芳基或芳基烷基！具有有价值的镇痛、抗炎、退烧和抗过敏活性，并具有抑制白三烯产生和抑制骨吸收的能力。它们相对于一般具有这些活性的化合物的副作用较少。
• USRE039420E1
  申请人：——

  公开号：——

  公开（公告）日：——
• 1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells
  作者：Haiyan Che、Truong Ngoc Tuyen、Hyun Pyo Kim、Haeil Park

  DOI：10.1016/j.bmcl.2010.05.092

  日期：2010.7

  A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE(2) production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Halogenated 1,5-Diarylimidazoles and Their Inhibitory Effects on LPS-Induced PGE2 Production in RAW 264.7 Cells
  作者：Zunhua Yang、Yuanying Fang、Jae-Min Kim、Kyung-Tae Lee、Haeil Park

  DOI：10.3390/molecules26206093

  日期：——

  A series of halogenated 1,5-diarylimidazole compounds were synthesized and their inhibitory effects on LPS-induced PGE2 production in RAW 264.7 cells were evaluated. A wide variety of 2,4-, 4-, and 2-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles were synthesized for SAR study via two different pathways. Overall, 4-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles, regardless of the species of halogen, exhibited very strong inhibitory activities of PGE2 production. Among them, 4-chloro-5-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)imidazole (3, IC50 3.3 nM ± 2.93), and 4-chloro-5-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)imidazole (13, IC50 5.3 nM ± 0.23) showed the best results.

  一系列卤代的1,5-二芳基咪唑化合物被合成，并评估了它们对RAW 264.7细胞中LPS诱导的PGE2产生的抑制作用。通过两种不同的途径合成了各种2,4-、4-和2-卤代的5-芳基-1-(4-甲基磺酰基苯基)咪唑，用于SAR研究。总体而言，无论卤素的种类如何，4-卤代的5-芳基-1-(4-甲基磺酰基苯基)咪唑都表现出非常强的PGE2产生抑制活性。其中，4-氯-5-(4-甲氧基苯基)-1-(4-甲基磺酰基苯基)咪唑(3，IC50 3.3 nM ± 2.93)和4-氯-5-(4-氯苯基)-1-(4-甲基磺酰基苯基)咪唑(13，IC50 5.3 nM ± 0.23)表现出最佳的结果。