(5-(氨基甲基)噻唑-2-基)氨基甲酸叔丁酯 | 878376-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (5-(氨基甲基)噻唑-2-基)氨基甲酸叔丁酯
• 中文别名: N-[5-(氨基甲基)-1,3-噻唑-2-基]氨基甲酸叔丁酯
• 英文名称: tert-butyl [5-(aminomethyl)-1,3-thiazol-2-yl]carbamate
• 英文别名: Tert-butyl N-[5-(aminomethyl)-1,3-thiazol-2-yl]carbamate
• CAS: 878376-13-7
• 化学式: C₉H₁₅N₃O₂S
• 分子量: 229.303
• InChiKey: BJBOIRJERIUSFM-UHFFFAOYSA-N

物化性质

• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-(氨基甲基)噻唑-2-基)氨基甲酸叔丁酯 、 间氟苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以100%的产率得到tert-butyl (5-{[(3-fluorobenzoyl)amino]methyl}-1,3-thiazol-2-yl)carbamate
  参考文献：
  名称：

  Discovery of Novel and Potent Thiazoloquinazolines as Selective Aurora A and B Kinase Inhibitors

  摘要：

  The synthesis of a novel series of quinazolines substituted at C4 by five-membered ring aminoheterocycles is reported. Their in vitro structure-activity relationships versus Aurora A and B serine-threonine kinases is discussed. Our results demonstrate that quinazolines with a substituted aminothiazole at C4 possess potent Aurora A and B inhibitory activity and excellent selectivity against a panel of various serine-threonine and tyrosine kinases, as exemplified by compound 46. We found also that the position and nature of the substituent on the thiazole play key roles in cellular potency. Compounds with an acetanilide substituent at C5' have the greatest cellular activity. The importance of the C5' position for substitution has been rationalized by ab initio molecular orbital calculations. Results show that the planar conformation with the sulfur of the thiazole next to the quinazoline N-3 is strongly favored over the other possible planar conformation. Compound 46 is a potent suppressor of the expression of phospho-histone H3 in tumor cells in vitro as well as in vivo, where 46, administered as its phosphate prodrug 54, suppresses the expression of phospho-histone H3 in subcutaneously implanted tumors in nude mice.

  DOI：

  10.1021/jm050786h
• 作为产物：
  描述：

  5-甲酰基噻唑-2-氨基甲酸叔丁酯 在 盐酸羟胺 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.5h， 生成 (5-(氨基甲基)噻唑-2-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Discovery of Novel and Potent Thiazoloquinazolines as Selective Aurora A and B Kinase Inhibitors

  摘要：

  The synthesis of a novel series of quinazolines substituted at C4 by five-membered ring aminoheterocycles is reported. Their in vitro structure-activity relationships versus Aurora A and B serine-threonine kinases is discussed. Our results demonstrate that quinazolines with a substituted aminothiazole at C4 possess potent Aurora A and B inhibitory activity and excellent selectivity against a panel of various serine-threonine and tyrosine kinases, as exemplified by compound 46. We found also that the position and nature of the substituent on the thiazole play key roles in cellular potency. Compounds with an acetanilide substituent at C5' have the greatest cellular activity. The importance of the C5' position for substitution has been rationalized by ab initio molecular orbital calculations. Results show that the planar conformation with the sulfur of the thiazole next to the quinazoline N-3 is strongly favored over the other possible planar conformation. Compound 46 is a potent suppressor of the expression of phospho-histone H3 in tumor cells in vitro as well as in vivo, where 46, administered as its phosphate prodrug 54, suppresses the expression of phospho-histone H3 in subcutaneously implanted tumors in nude mice.

  DOI：

  10.1021/jm050786h

文献信息

• [EN] QUATERNARY AMMONIUM CATION SUBSTITUTED COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS À SUBSTITUTION PAR CATIONS AMMONIUM QUATERNAIRES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：[en]F. HOFFMANN-LA ROCHE AG

  公开号：WO2023280733A1

  公开（公告）日：2023-01-12

  The invention provides novel heterocyclic compounds having the general formula (I), and pharmaceutically acceptable salts thereof, wherein R1to R6are as described herein. Further provided are pharmaceutical compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds as medicaments, in particular methods of using the compounds as antibiotics for the treatment or prevention of bacterial infections and resulting diseases.
• Discovery of Novel and Potent Thiazoloquinazolines as Selective Aurora A and B Kinase Inhibitors
  作者：Frédéric H. Jung、Georges Pasquet、Christine Lambert-van der Brempt、Jean-Jacques M. Lohmann、Nicolas Warin、Fabrice Renaud、Hervé Germain、Chris De Savi、Nicola Roberts、Trevor Johnson、Cyril Dousson、George B. Hill、Andrew A. Mortlock、Nicola Heron、Robert W. Wilkinson、Stephen R. Wedge、Simon P. Heaton、Rajesh Odedra、Nicholas J. Keen、Stephen Green、Elaine Brown、Katherine Thompson、Stephen Brightwell

  DOI：10.1021/jm050786h

  日期：2006.2.1

  The synthesis of a novel series of quinazolines substituted at C4 by five-membered ring aminoheterocycles is reported. Their in vitro structure-activity relationships versus Aurora A and B serine-threonine kinases is discussed. Our results demonstrate that quinazolines with a substituted aminothiazole at C4 possess potent Aurora A and B inhibitory activity and excellent selectivity against a panel of various serine-threonine and tyrosine kinases, as exemplified by compound 46. We found also that the position and nature of the substituent on the thiazole play key roles in cellular potency. Compounds with an acetanilide substituent at C5' have the greatest cellular activity. The importance of the C5' position for substitution has been rationalized by ab initio molecular orbital calculations. Results show that the planar conformation with the sulfur of the thiazole next to the quinazoline N-3 is strongly favored over the other possible planar conformation. Compound 46 is a potent suppressor of the expression of phospho-histone H3 in tumor cells in vitro as well as in vivo, where 46, administered as its phosphate prodrug 54, suppresses the expression of phospho-histone H3 in subcutaneously implanted tumors in nude mice.