1-(3-(1H-imidazol-1-yl)propyl)-3-methylthiourea | 259753-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-(1H-imidazol-1-yl)propyl)-3-methylthiourea
• 英文别名: 1-[3-(1H-imidazol-1-yl)propyl]-3-methylthiourea；1-(3-imidazol-1-ylpropyl)-3-methylthiourea
• CAS: 259753-98-5
• 化学式: C₈H₁₄N₄S
• mdl: MFCD01329882
• 分子量: 198.292
• InChiKey: IKGBJMGGNGHTRK-UHFFFAOYSA-N

物化性质

• 熔点：
  122-122.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  371.0±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(3-氨基丙基)咪唑 、 异硫氰酸甲酯 以 乙醇 为溶剂， 反应 8.0h， 以80%的产率得到1-(3-(1H-imidazol-1-yl)propyl)-3-methylthiourea
  参考文献：
  名称：

  NOVEL GENES RELATED TO GLUTAMINYL CYCLASE

  摘要：

  小说谷氨酰肽环转移酶样蛋白（QPCTLs），它们是谷氨酰环化酶（QC，EC 2.3.2.5）的同工酶，以及编码这些同工酶的分离核酸，所有这些对于发现新的治疗药物、测量环化酶活性以及确定化合物对这些谷氨酰环化酶同工酶的抑制活性都是有用的。

  公开号：

  US20080249083A1

文献信息

• Novel inhibitors of glutaminyl cyclase
  申请人：Schilling Stephan

  公开号：US20050215573A1

  公开（公告）日：2005-09-29

  The present invention relates to novel inhibitors of glutaminyl cyclase and combinations thereof for the treatment of neuronal disorders, especially Alzheimer's disease, Down Syndrome, Parkinson disease, Chorea Huntington, pathogenic psychotic conditions, schizophrenia, impaired food intake, sleep-wakefulness, impaired homeostatic regulation of energy metabolism, impaired autonomic function, impaired hormonal balance, impaired regulation, body fluids, hypertension, fever, sleep dysregulation, anorexia, anxiety related disorders including depression, seizures including epilepsy, drug withdrawal and alcoholism, neurodegenerative disorders including cognitive dysfunction and dementia.

  本发明涉及新型谷氨酰环化酶抑制剂及其组合物，用于治疗神经系统疾病，特别是阿尔茨海默病、唐氏综合征、帕金森病、亨廷顿舞蹈症、致病性精神病症、精神分裂症、食欲受损、睡眠-觉醒、体内能量代谢的失衡、自主神经功能受损、激素平衡受损、调节失调、体液平衡、高血压、发热、睡眠失调、厌食症、焦虑相关疾病包括抑郁症、癫痫发作包括癫痫、药物戒断和酗酒、神经退行性疾病包括认知功能障碍和痴呆症。
• The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship
  作者：Mirko Buchholz、Ulrich Heiser、Stephan Schilling、André J. Niestroj、Katrin Zunkel、Hans-Ulrich Demuth

  DOI：10.1021/jm050756e

  日期：2006.1.1

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.
• NOVEL INHIBITORS OF GLUTAMINYL CYCLASE
  申请人：Probiodrug AG

  公开号：EP1713780B1

  公开（公告）日：2012-01-18
• NEW USE OF GLUTAMINYL CYCLASE INHIBITORS
  申请人：Probiodrug AG

  公开号：EP2117540A1

  公开（公告）日：2009-11-18
• USE OF EFFECTORS OF GLUTAMINYL AND GLUTAMATE CYCLASES
  申请人：Hoffmann Torsten

  公开号：US20070191366A1

  公开（公告）日：2007-08-16

  The present invention provides novel physiological substrates of mammalian glutaminyl cyclase (QC, EC 2.3.2.5), new effectors of QC, methods for screening for such effectors, and the use of such effectors and pharmaceutical compositions comprising such effectors for the treatment of conditions that can be treated by modulation of QC-activity. Preferred compositions additionally comprise inhibitors of DP IV or DP IV-like enzymes for the treatment or alleviation of conditions that can be treated by modulation of QC- and DP IV-activity.