2-Benzylmercapto-4,5-diphenyl-imidazol | 50596-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Benzylmercapto-4,5-diphenyl-imidazol
• 英文别名: 2-(benzylsulfanyl)-4,5-diphenyl-1H-imidazole；2-benzylsulfanyl-4,5-diphenyl-1H-imidazole
• CAS: 50596-61-7
• 化学式: C₂₂H₁₈N₂S
• 分子量: 342.464
• InChiKey: ROTUJQFQEFHPJK-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185 °C(Solv: ethanol (64-17-5))
• 沸点：
  545.4±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzylmercapto-4,5-diphenyl-imidazol 在 potassium tert-butylate 、 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-((difluoro(phenyl)methyl)sulfonyl)-1-methyl-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy

  摘要：

  Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors (2 and 3) with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor 28a, with EC50 values of 0.88 and 0.81 mu M against IAV strain WSN and MeV strain Edmonston, respectively. It was also found that compound 28a delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish 28a as a promising lead for antiviral therapy through a host-directed mechanism.

  DOI：

  10.1021/ml400166b
• 作为产物：
  描述：

  溴甲苯 、 4,5-二苯基-2-咪唑硫醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-Benzylmercapto-4,5-diphenyl-imidazol
  参考文献：
  名称：

  Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy

  摘要：

  Targeting host cell factors required for virus replication provides an alternative to targeting pathogen components and represents a promising approach to develop broad-spectrum antiviral therapeutics. High-throughput screening (HTS) identified two classes of inhibitors (2 and 3) with broad-spectrum antiviral activity against ortho- and paramyxoviruses including influenza A virus (IAV), measles virus (MeV), respiratory syncytial virus (RSV), and human parainfluenza virus type 3 (HPIV3). Hit-to-lead optimization delivered inhibitor 28a, with EC50 values of 0.88 and 0.81 mu M against IAV strain WSN and MeV strain Edmonston, respectively. It was also found that compound 28a delivers good stability in human liver S9 fractions with a half-life of 165 min. These data establish 28a as a promising lead for antiviral therapy through a host-directed mechanism.

  DOI：

  10.1021/ml400166b

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。
• Regioselectivity of the reactions of 4,5-diphenylimidazole-2-thione with 1-chloro-2,3-epoxy-propane and 1-bromo-propene, efficient precursors for imidazo[2,1-<i>b</i>]thiazine and thiazole. Effect of microwave and solid support
  作者：Mohamed. R. Aouad、Nadje T. Rezki、El Sayed H. El Ahsry

  DOI：10.1002/jhet.5570450511

  日期：2008.9

  A regioselective allylation of 1 with allyl bromide in presence of triethylamine gave the S-allyl 8, while in presence of potassium carbonate led to the S,N-bis(allylated) derivative 9. The intramolecular ring closure of 8 in presence of sulfuric acid afforded the imidazothiazole 16. Protection of the sulfur in 1 and subsequent reaction with allyl bromide gave the N-allylated derivative and with 2 gave

  在没有溶剂的微波（MW）照射下，固体支持物可以选择性地合成2,3-环氧-丙基-硫代咪唑4，并禁止其环化，从而使咪唑并[2,1- b ]噻嗪3发生反应。 4,5-二苯基咪唑-2-硫酮（1）与1-氯-2,3-环氧丙烷（2）。后者的形成需要成为其唯一产品的基本条件；碱性催化剂的变化改变了常规和微波（MW）条件下两种产物的比例。在三乙胺的存在下，用烯丙基溴对1进行区域选择性烯丙基化，得到S-烯丙基8，而在碳酸钾的存在下导致S，N-双（烯丙基化）衍生物9。在硫酸存在下的分子内8的闭环得到咪唑并噻唑16。在1中保护硫，然后与烯丙基溴反应，得到N-烯丙基化衍生物，与2反应得到N-3-氯-丙-1-基衍生物，这为形成3和4的优选路线提供了线索。理论上已经通过使用AM1方法研究了1与2的烷基化过程中遇到的反应性。
• Mathew; Purushothaman, Journal of the Indian Chemical Society, 1991, vol. 68, # 12, p. 670 - 672
  作者：Mathew、Purushothaman

  DOI：——

  日期：——
• POVSTYANOJ M. V.; PRIJMENKO B. A.; KOCHERGIN P. M., XIM.-FARMATSEVT. ZH., 1978, 12, HO 5, 59-62
  作者：POVSTYANOJ M. V.、 PRIJMENKO B. A.、 KOCHERGIN P. M.

  DOI：——

  日期：——
• EP0519996A1
  申请人：——

  公开号：EP0519996A1

  公开（公告）日：1992-12-30