1-[1-dimethylaminomethylidene]-3-propylthiourea | 905300-33-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[1-dimethylaminomethylidene]-3-propylthiourea
• 英文别名: 1-(Dimethylaminomethylidene)-3-propylthiourea；1-(dimethylaminomethylidene)-3-propylthiourea
• CAS: 905300-33-6
• 化学式: C₇H₁₅N₃S
• 分子量: 173.282
• InChiKey: MHDZBMPFISZKNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[1-dimethylaminomethylidene]-3-propylthiourea 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.25h， 生成 {5-[3-(4-chlorophenyl)pyridin-4-yl]thiazol-2-yl}propylamine
  参考文献：
  名称：

  Discovery, Development, and SAR of Aminothiazoles as LIMK Inhibitors with Cellular Anti-Invasive Properties

  摘要：

  As part of a program to develop a small molecule inhibitor of LIMK, a series of aminothiazole inhibitors were discovered by high throughput screening. Scaffold hopping and subsequent SAR directed development led to a series of low nanomolar inhibitors of LIMK1 and LIMK2 that also inhibited the direct biomarker p-cofilin in cells and inhibited the invasion of MDA MB-231-luc cells in a matrigel inverse invasion assay.

  DOI：

  10.1021/acs.jmedchem.5b01242
• 作为产物：
  描述：

  正丙基硫脲 、 N,N-二甲基甲酰胺 在 N,N-二甲基乙酰胺 作用下， 以 乙醇 为溶剂， 生成 1-[1-dimethylaminomethylidene]-3-propylthiourea
  参考文献：
  名称：

  Utilization of a nitrogen–sulfur nonbonding interaction in the design of new 2-aminothiazol-5-yl-pyrimidines as p38α MAP kinase inhibitors

  摘要：

  The design, synthesis, and structure-activity relationships (SAR) of a series of 2-aminothiazol-5-yl-pyrimidines as novel p38α MAP kinase inhibitors are described. These efforts led to the identification of 41 as a potent p38α inhibitor that utilizes a unique nitrogen-sulfur intramolecular nonbonding interaction to stabilize the conformation required for binding to the p38α active site. X-ray crystallographic studies that confirm the proposed binding mode of this class of inhibitors in p38 α and provide evidence for the proposed intramolecular nitrogen-sulfur interaction are discussed.

  DOI：

  10.1016/j.bmcl.2010.07.102

文献信息

• A study on synthesis, antioxidant, anticancer activities and docking study of novel benzimidazoloyl thiazole derivatives
  作者：Chithra、Brindha、Mariappan、Simon, Turibius、Abbs Fen Reji

  DOI：10.56042/ijc.v62i6.2514

  日期：——
• Utilization of a nitrogen–sulfur nonbonding interaction in the design of new 2-aminothiazol-5-yl-pyrimidines as p38α MAP kinase inhibitors
  作者：Shuqun Lin、Stephen T. Wrobleski、John Hynes、Sidney Pitt、Rosemary Zhang、Yi Fan、Arthur M. Doweyko、Kevin F. Kish、John S. Sack、Mary F. Malley、Susan E. Kiefer、John A. Newitt、Murray McKinnon、James Trzaskos、Joel C. Barrish、John H. Dodd、Gary L. Schieven、Katerina Leftheris

  DOI：10.1016/j.bmcl.2010.07.102

  日期：2010.10

  The design, synthesis, and structure-activity relationships (SAR) of a series of 2-aminothiazol-5-yl-pyrimidines as novel p38α MAP kinase inhibitors are described. These efforts led to the identification of 41 as a potent p38α inhibitor that utilizes a unique nitrogen-sulfur intramolecular nonbonding interaction to stabilize the conformation required for binding to the p38α active site. X-ray crystallographic studies that confirm the proposed binding mode of this class of inhibitors in p38 α and provide evidence for the proposed intramolecular nitrogen-sulfur interaction are discussed.
• Discovery, Development, and SAR of Aminothiazoles as LIMK Inhibitors with Cellular Anti-Invasive Properties
  作者：Mark D. Charles、Joanna L. Brookfield、Tennyson C. Ekwuru、Martin Stockley、John Dunn、Michelle Riddick、Tim Hammonds、Elisabeth Trivier、Gavin Greenland、Ai Ching Wong、Anne Cheasty、Susan Boyd、Diane Crighton、Michael F. Olson

  DOI：10.1021/acs.jmedchem.5b01242

  日期：2015.10.22

  As part of a program to develop a small molecule inhibitor of LIMK, a series of aminothiazole inhibitors were discovered by high throughput screening. Scaffold hopping and subsequent SAR directed development led to a series of low nanomolar inhibitors of LIMK1 and LIMK2 that also inhibited the direct biomarker p-cofilin in cells and inhibited the invasion of MDA MB-231-luc cells in a matrigel inverse invasion assay.