4(5)-(4-chlorophenyl)-2,3-dihydro-5(4)-phenyl-1H-imidazole-2-thione | 23187-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4(5)-(4-chlorophenyl)-2,3-dihydro-5(4)-phenyl-1H-imidazole-2-thione
• 英文别名: 4-(p-Chlor-phenyl)-5-phenyl-Δ⁴-imidazolinthion-(2)；4-p-Chlorphenyl-5-phenyl-4-imidazolin-2-thion；4-(4-chloro-phenyl)-5-phenyl-1,3-dihydro-imidazole-2-thione；4-(4-Chlorophenyl)-5-phenyl-1,3-dihydroimidazole-2-thione
• CAS: 23187-09-9
• 化学式: C₁₅H₁₁ClN₂S
• 分子量: 286.785
• InChiKey: ZYTWLVOCKZACEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4(5)-(4-chlorophenyl)-2,3-dihydro-5(4)-phenyl-1H-imidazole-2-thione 在 氯磺酸 、 ammonium hydroxide 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 4-[5-(4-Chloro-phenyl)-2-ethylsulfanyl-3H-imidazol-4-yl]-benzenesulfonamide
  参考文献：
  名称：

  Syntheses of 2-Alkylthio-(4,5-Diaryl)imidazoles

  摘要：

  A series of 2-alkylthio-4,5-diarylimidazoles were synthesized in three steps. The reaction of ammonium thiocyanate with benzoylbenzoins 4 gave 4,5-diarylimidazole-2-thiones 5. Alkylation of compound 5 with alkyl iodide yielded 2-alkylthio-4,5-diarylimidazoles 6. Chlorosulfonation of compound 6 followed by ammonia gave the desired compounds 4-[2-alkylthio-4(5)-(4-substituted phenyl)imidazole-5(4)-yl]benzensulfonamides 7.

  DOI：

  10.1080/104265090884265
• 作为产物：
  描述：

  4-氯苯甲醛 、 苯甲醛 在 potassium cyanide 、 水 作用下， 以 甲醇 、 正丁醇 为溶剂， 生成 4(5)-(4-chlorophenyl)-2,3-dihydro-5(4)-phenyl-1H-imidazole-2-thione
  参考文献：
  名称：

  Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors

  摘要：

  A series of 4,5-diaryl-1H-imidazole-2(3H)-thione was synthesized and their inhibitory potency against soybean 15-lipoxygenase and free radical scavenging activities were determined. Compound 11 showed the best IC50 for 15-LOX inhibition (IC50 = 4.7 mu M) and free radical scavenging activity (IC50 = 14 mu M). Methylation of SH at C-2 position of imidazole has dramatically decreased the 15-LOX inhibition and radical scavenging activity as it can be observed in the inactive compound 14 (IC50 >250 mu M). Structure activity similarity (SAS) showed that the most important chemical modification in this series was methylation of SH group and Docking studies revealed a proper orientation for SH group towards Fe core of the 15-LOX active site. Therefore it was concluded that iron chelating could be a possible mechanism for enzyme inhibition in this series of compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.050

文献信息

• Acyl-CoA: cholesterol O-acyl transferase (ACAT) inhibitors. 1. 2-(Alkylthio)-4,5-diphenyl-1H-imidazoles as potent inhibitors of ACAT
  作者：Neil V. Harris、Andrew W. Bridge、Raymond C. Bush、Edward C. J. Coffee、Donald I. Dron、Mark F. Harper、Michael J. Ashton、David J. Lythgoe、Christopher Smith

  DOI：10.1021/jm00101a016

  日期：1992.11

  potent, bioavailable ACAT inhibitor may have beneficial effects in the treatment of atherosclerosis by (i) reducing the absorption of dietary cholesterol, (ii) reducing the secretion of very low density lipoproteins into plasma from the liver, and (iii) preventing the transformation of arterial macrophages into foam cells. We have found that a mevalonate derivative 2, which contains a 4,5-diphenyl-1H-imidazol-2-yl

  生物有效的有效ACAT抑制剂可通过（i）减少饮食中胆固醇的吸收，（ii）减少极低密度脂蛋白从肝脏向血浆的分泌以及（iii）防止转化而对动脉粥样硬化产生有益作用巨噬细胞进入泡沫细胞。我们已经发现，含有4,5-二苯基-1H-咪唑-2-基部分的甲羟戊酸酯衍生物2在体外抑制大鼠肝微粒体ACAT，并在胆固醇喂养的大鼠中产生明显的降胆固醇作用。2的类似物的结构活性关系表明，4,5-二苯基-1H-咪唑部分是抑制大鼠微粒体ACAT的药效基团。
• Preparation, antiarthritic and analgesic activity of 4,5-diaryl-2-(substituted thio)-1H-imidazoles and their sulfoxides and sulfones
  作者：Thomas R. Sharpe、Saul C. Cherkofsky、Walter E. Hewes、Dewey H. Smith、Walter A. Gregory、Stephen B. Haber、Michael R. Leadbetter、Joel G. Whitney

  DOI：10.1021/jm00147a011

  日期：1985.9

  A series of 4,5-diaryl-2-(substituted thio)-1H-imidazoles was synthesized and evaluated as antiinflammatory and analgesic agents in the rat adjuvant induced arthritis assay and the mouse phenyl-p-benzoquinone writhing (PQW) assay. Several analogues were found to be more potent than phenylbutazone and indomethacin. Structure-activity relationships are discussed. One of the compounds, 4,5-bis(4-fluorophenyl)-2-[(1

  合成了一系列的4,5-二芳基-2-（取代硫代）-1H-咪唑，并在大鼠佐剂诱导的关节炎试验和小鼠苯基-对苯醌扭曲（PQW）试验中用作抗炎和镇痛药。发现几种类似物比苯基丁a和消炎痛更有效。讨论了构效关系。发现其中一种化合物4,5-双（4-氟苯基）-2-[（（1,1,2,2-四氟乙基）-磺酰基] -1H-咪唑（8d，tiflamizole）是在大鼠佐剂诱导的关节炎试验中具有消炎痛的作用，目前正在作为抗关节炎药进行临床试验。
• 2-Mercapto-4,5-diarylimidazole derivatives and the use thereof as cyclooxygenase inhibitors
  申请人：——

  公开号：US20040116695A1

  公开（公告）日：2004-06-17

  The invention relates to the 2-mercapto-4,5-diarylimidazole derivatives of formula (I), wherein R 1 , R 2 , R 3 and R 4 are defined as in the description. The inventive compounds have an immunomodulatory and cyclooxygenase-inhibiting activity and are therefore suitable for the treatment of diseases that are associated with a disturbed immune system.

  本发明涉及公式(I)的2-巯基-4,5-二芳基咪唑衍生物，其中R1、R2、R3和R4如描述中所定义。该发明化合物具有免疫调节和环氧合酶抑制活性，因此适用于治疗与免疫系统紊乱有关的疾病。
• 2-Mercapto-4,5-Diarylimidazole Derivatives and the use thereof as Cyclooxygenase Inhibitors
  申请人：Dannhardt Gerd

  公开号：US20070185169A1

  公开（公告）日：2007-08-09

  The invention relates to the 2-mercapto-4,5-diarylimidazole derivatives of formula (I), wherein R 1 , R 2 , R 3 and R 4 are defined as in the description. The inventive compounds have an immunomodulatory and cyclooxygenase-inhibiting activity and are therefore suitable for the treatment of disease that are associated with a disturbed immune system.

  本发明涉及公式（I）中的2-巯基-4,5-二芳基咪唑衍生物，其中R1、R2、R3和R4如说明书中所定义。这些创新化合物具有免疫调节和环氧合酶抑制活性，因此适用于治疗与免疫系统紊乱相关的疾病。
• SHARPE, T. R.;CHERKOFSKY, S. C.;HEWES, W. E.;SMITH, D. H.;GREGORY, W. A.;+, J. MED. CHEM., 1985, 28, N 9, 1188-1194
  作者：SHARPE, T. R.、CHERKOFSKY, S. C.、HEWES, W. E.、SMITH, D. H.、GREGORY, W. A.、+

  DOI：——

  日期：——