tert-butyl 4-(4-(benzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate | 220697-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(4-(benzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate
• 英文别名: tert-butyl 4-[4-(1,3-benzothiazol-2-yl)phenyl]piperazine-1-carboxylate
• CAS: 220697-60-9
• 化学式: C₂₂H₂₅N₃O₂S
• 分子量: 395.525
• InChiKey: AABPNIOPVYPZMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-(benzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate 在 甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-(4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)phenyl)benzo[d]thiazole
  参考文献：
  名称：

  Discovery and Preliminary Structure–Activity Relationship of Arylpiperazines as Novel, Brain-Penetrant Antiprion Compounds

  摘要：

  Creutzfeldt-Jakob disease and kuru in humans, BSE in cattle, and scrapie in sheep are fatal neurodegenerative disorders. Such illnesses are caused by the conversion and accumulation of a misfolded pathogenic isoform (termed PrPSc) of a normally benign, host cellular protein, denoted PrPC. We employed high-throughput screening enzyme-linked immunosorbent assays to evaluate compounds for their ability to reduce the level of PrPSc in Rocky Mountain Laboratory prion-infected mouse neuroblastoma cells (ScN2a-cl3). Arylpiperazines were among the active compounds identified, but the initial hits suffered from low potency and poor drug-likeness. The best of those hits, such as 1, 7, 13, and 19, displayed moderate antiprion activity with EC50 values in the micromolar range. Key analogues were designed and synthesized on the basis of the structure-activity relationship, with analogues 41, 44, 46, and 47 found to have submicromolar potency. Analogues 41 and 44 were able to penetrate the blood-brain barrier and achieved excellent drug concentrations in the brains of mice after oral dosing. These compounds represent good starting points for further lead optimization in our pursuit of potential drug candidates for the treatment of prion diseases.

  DOI：

  10.1021/ml300472n
• 作为产物：
  描述：

  2-氨基苯硫醇 、 1-BOC-4-(4-甲酰苯基)哌嗪 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.45h， 以67%的产率得到tert-butyl 4-(4-(benzo[d]thiazol-2-yl)phenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Bhattacharyya, Bhaswati; Dhara, Kaliprasanna, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1749 - 1759

  摘要：

  DOI：