4,5-二对甲苯-1,3-二氢咪唑-2-硫酮 | 73181-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5-二对甲苯-1,3-二氢咪唑-2-硫酮
• 英文名称: 2,3-dihydro-4,5-bis-(4-methylphenyl)-1H-imidazole-2-thione
• 英文别名: 4,5-di-(p-tolyl)-Δ⁴-imidazoline-2-thione；4,5-di-p-tolyl-1,3-dihydro-imidazole-2-thione；4,5-di-p-tolyl-1,3-dihydro-imidazole-2-thione；4,5-Di-p-tolyl-Δ⁴-imidazolin-thion-(2)；4,5-bis(4-methylphenyl)-1,3-dihydroimidazole-2-thione
• CAS: 73181-95-0
• 化学式: C₁₇H₁₆N₂S
• mdl: MFCD06654917
• 分子量: 280.393
• InChiKey: RSZJNDGSQUBMTF-UHFFFAOYSA-N

物化性质

• 熔点：
  332 °C
• 沸点：
  433.8±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  4,5-二对甲苯-1,3-二氢咪唑-2-硫酮 在 吡啶 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 7H-2,3-di-(p-tolyl)imidazo<2,1-b><1,3>thiazin-5(6H)-one
  参考文献：
  名称：

  Mohan, Jag; Anjaneyulu, G. S. R.; Kiran, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, p. 570 - 572

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-二甲基苯甲酸 以63%的产率得到
  参考文献：
  名称：

  PURUSHOTHAMAN, E.;RAJASEKHARAN, PILLAI RAJAI V. N., INDIAN J. CHEM. B, 29,(1990) N, C. 18-21

  摘要：

  DOI：

文献信息

• Antiinflammatory imidazole derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04402960A1

  公开（公告）日：1983-09-06

  Imidazole derivatives of the formula ##STR1## wherein AR.sub.1 and AR.sub.2 each independently is phenyl, optionally substituted by halogen atoms, alkyl residues, alkoxy residues; or dialkylamino residues; pyridyl, furyl; or thienyl; R.sub.1 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy groups, alkoxy groups, or acyloxy groups; benzyl; tetrahydropyran-2-yl; or tetrahydrofuran-2-yl; n is 0, 1 or 2; and Z is phenyl optionally substituted by halogen atoms, alkyl groups, alkoxy groups, nitro groups, amino, acylamino groups or trifluoromethyl groups; pyridyl; N-oxypyridyl; pyrimidinyl; thiazolyl; or thienyl, and the physiologically acceptable salts thereof with acids, have valuable pharmacological activity, e.g., antiinflammatory activity.

  咪唑衍生物的化学式为##STR1##其中AR.sub.1和AR.sub.2各自独立地是苯基，可以选择地被卤原子，烷基残基，烷氧基残基; 或二烷基氨基残基; 吡啶基，呋喃基; 或噻吩基; R.sub.1是氢; 1-6个碳原子的烷基，可以选择地被羟基，烷氧基或酰氧基取代; 苄基; 四氢吡喃-2-基; 或四氢呋喃-2-基; n为0, 1或2; Z是苯基，可以选择地被卤原子，烷基，烷氧基，硝基，氨基，酰胺基或三氟甲基取代; 吡啶基; N-氧基吡啶基; 嘧啶基; 噻唑基; 或噻吩基，以及其与酸形成的生理上可接受的盐具有有价值的药理活性，例如抗炎活性。
• Design, Synthesis, and Structure-Activity Relationship Studies for a New Imidazole Series of J774 Macrophage Specific Acyl-CoA:Cholesterol Acyltransferase (ACAT) Inhibitors
  作者：Thomas P. Maduskuie、Richard G. Wilde、Jeffrey T. Billheimer、Debra A. Cromley、Sandra Germain、Peter J. Gillies、C. Anne Higley、Alex L. Johnson、Penio Pennev、Edward J. Shimshick、Ruth R. Wexler

  DOI：10.1021/jm00007a004

  日期：1995.3

  Acyl-CoA:cholesterol acyltransferase (ACAT) is the primary enzyme involved in intracellular cholesterol esterification. Arterial wall infiltration by macrophages and subsequent uncontrolled esterification of cholesterol leading to foam cell formation is believed to be an important process which leads to the development of fatty streaks. Inhibitors of the ACAT enzyme may retard this atherogenic process

  酰基辅酶A：胆固醇酰基转移酶（ACAT）是参与细胞内胆固醇酯化的主要酶。巨噬细胞的动脉壁浸润和随后的胆固醇不受控制的酯化导致泡沫细胞形成被认为是导致脂肪条纹发展的重要过程。ACAT酶的抑制剂可能会延迟该动脉粥样硬化过程。我们最近发现了一系列咪唑，它们在J774巨噬细胞细胞培养测定中是有效的体外ACAT抑制剂。本文将描述这一系列非常有效的化合物的设计，合成和结构-活性关系。
• 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。
• Antiinflammatory-4,5-diphenyl-2-substituted-thio-imidazoles and their
  申请人：Schering Aktiengesellschaft

  公开号：US04269847A1

  公开（公告）日：1981-05-26

  Imidazole derivatives of the formula ##STR1## wherein Ar.sub.1 and Ar.sub.2 are each phenyl; phenyl substituted by halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.2-6 dialkylamino; pyridyl; furyl; or thienyl; with the proviso that Ar.sub.1 and Ar.sub.2 are not both unsubstituted phenyl; R.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by hydroxy, C.sub.1-4 alkoxy or C.sub.1-6 alkanoyloxy; n is 0, 1 or 2; and Z is a C.sub.2-6 -alkyl or -alkenyl residue substituted by one or two of hydroxy, C.sub.1-4 alkoxy, C.sub.2-8 alkylenedioxy, C.sub.1-6 alkanoyloxy or benzoyloxy, or by one alkoxycarbonyl group; and the salts thereof with physiologically acceptable acids, possess valuable pharmacological properties.

  咪唑衍生物的化学式为##STR1##其中Ar.sub.1和Ar.sub.2均为苯基；苯基被卤素、C.sub.1-4烷基、C.sub.1-4烷氧基或C.sub.2-6二烷基氨基取代；吡啶基；呋喃基；或噻吩基；但Ar.sub.1和Ar.sub.2不能都是未取代的苯基；R.sub.1为氢、C.sub.1-4烷基或C.sub.1-4烷基被羟基、C.sub.1-4烷氧基或C.sub.1-6烷酰氧基取代；n为0、1或2；Z为C.sub.2-6-烷基或-烯基残基，被一个或两个羟基、C.sub.1-4烷氧基、C.sub.2-8烷二氧基、C.sub.1-6烷酰氧基或苯甲酰氧基取代，或者被一个烷氧羰基基团取代；以及其与生理上可接受的酸形成的盐具有有价值的药理学性质。