4-n-butylphenylthiourea | 65069-56-9

• 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: 4-n-butylphenylthiourea
• 英文别名: N-(4-butylphenyl)thiourea；(4-butylphenyl)thiourea
• CAS: 65069-56-9
• 化学式: C₁₁H₁₆N₂S
• 分子量: 208.327
• InChiKey: RZJUXUZQNIADNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-n-butylphenylthiourea 、 3-(2-溴乙酰基)吡啶氢溴酸盐 在 HMCM-41 作用下， 以 甲醇 为溶剂， 以65%的产率得到N-(4-n-butylphenyl)-4-(3-pyridyl)thiazol-2-amine hydrobromide
  参考文献：
  名称：

  Novel synthetic approach to N-aryl-4-(3-pyridyl)thiazol-2-amine and analogues using HMCM-41 as catalyst, and their biological evaluation as human platelet aggregation inhibitors

  摘要：

  A novel synthetic approach to N-aryl-4-(3-pyridyl)thiazol-2-amine and analogues using HMCM-41, a mesoporous aluminosilicate catalyst and their in vitro ADP-induced platelet aggregation inhibitory activity on human blood platelets is described. Among the test compounds N-(2'flourophenyl)-4-(3-pyridyl)thiazol-2-amine (9e) was found to be the most potent, IC50 = 4.84 x 10(-7) M. (c) 2007 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2007.01.016
• 作为产物：
  描述：

  4-丁基苯铵氯化物 、 ammonium thiocyanate 以60%的产率得到4-n-butylphenylthiourea
  参考文献：
  名称：

  Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

  摘要：

  制备芳基硫脲的改进方法包括将苯甲酰异硫氰酸酯与苯胺在丙酮中反应，然后用5%氢氧化钠水溶液对生成的N-芳基-N'-苯甲酰硫脲进行去苯甲酰化。双环烷基硫脲和N-(芳烷基)硫脲（例如9H-9-芴基硫脲）可直接由相应的异硫氰酸酯与氨反应制备。

  DOI：

  10.1055/s-1988-27605

文献信息

• Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas
  作者：C. R. Rasmussen、F. J. Villani, Jr.、L. E. Weaner、B. E. Reynolds、A. R. Hood、L. R. Hecker、S. O. Nortey、A. Hanslin、M. J. Costanzo、E. T. Powell、A. J. Molinari

  DOI：10.1055/s-1988-27605

  日期：——

  An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N′-benzoylthioureas with 5% aqueous sodium hydroxide. Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g., 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.

  制备芳基硫脲的改进方法包括将苯甲酰异硫氰酸酯与苯胺在丙酮中反应，然后用5%氢氧化钠水溶液对生成的N-芳基-N'-苯甲酰硫脲进行去苯甲酰化。双环烷基硫脲和N-(芳烷基)硫脲（例如9H-9-芴基硫脲）可直接由相应的异硫氰酸酯与氨反应制备。
• A Versatile Synthesis of Novel<i>N</i>,<i>N</i>,<i>N</i>″-Trisubstituted Guanidines
  作者：C. R. Rasmussen、F. J. Villani, Jr.、B. E. Reynolds、J. N. Plampin、A. R. Hood、L. R. Hecker、S. O. Nortey、A. Hanslin、M. J. Costanzo、R. M. Howse, Jr.、A. J. Molinari

  DOI：10.1055/s-1988-27606

  日期：——

  N,N,N″-Trisubstituted guanidines (most of them N″-aryl-N-azacycloalkanecarboximidamides) are prepared in generally good yields by S-methylation of monosubstituted thioureas with methyl iodide in methanol or acetone and reaction of the resultant methyl carbamimidothioate hydroiodides with secondary amines in boiling tert-butyl alcohol or acetonitrile.

  N,N,N″-三取代胍（大部分是N″-芳基-N-氮杂环烷羧基亚胺）通常以良好的产率通过以下步骤制备：将单取代硫脲与甲基碘在甲醇或丙酮中进行S-甲基化反应，然后将所得的甲基氨基甲亚胺硫醇氢碘酸盐与二级胺在沸腾的叔丁醇或丙酮腈中反应。
• N-Phenyl-4-phenyl-1-piperazine carboxamidines and related compounds as antiarrhythmic agents
  申请人：LABORATOIRES SYNTEX S.A.

  公开号：EP0204265A1

  公开（公告）日：1986-12-10

  Compounds having the formula and the tautomers thereof wherein R, R1, R2, R3, R4 and R5 have the definitions given herein, are useful as antiarrhythmic agents.

  具有以下式子的化合物 及其同系物，其中 R、R1、R2、R3、R4 和 R5 具有本文给出的定义，可用作抗心律失常药物。
• New antiarrhythmic agents. Piperazine guanidine derivatives
  作者：Jean-Claude Pascal、Henri Pinhas、Francette Laure、Danièle Dumez、Alain Poizot

  DOI：10.1016/0223-5234(90)90169-4

  日期：1990.2
• 2-N-Arylthiazole inhibitors of Mycobacterium tuberculosis
  作者：Michael P. Clark、Tiansheng Wang、Emanuele Perola、David D. Deininger、Harmon J. Zuccola、Steven M. Jones、Hong Gao、Brian C. VanderVen、David G. Russell、Carolyn M. Shoen、Michael H. Cynamon、John A. Thomson、Christopher P. Locher

  DOI：10.1016/j.bmcl.2017.07.067

  日期：2017.9

  To develop agents for the treatment of infections caused by Mycobacterium tuberculosis, a novel phenotypic screen was undertaken that identified a series of 2-N-aryl thiazole-based inhibitors of intracellular Mycobacterium tuberculosis. Analogs were optimized to improve potency against an attenuated BSL2 H37Ra laboratory strain cultivated in human macrophage cells in vitro. The insertion of a carboxylic acid functionality resulted in compounds that retained potency and greatly improved microsomal stability. However, the strong potency trends we observed in the attenuated H37Ra strain were inconsistent with the potency observed for virulent strains in vitro and in vivo. (C) 2017 Elsevier Ltd. All rights reserved.