2-phenyl-benzo[b]thiophen-3-one | 53614-69-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenyl-benzo[b]thiophen-3-one
• 英文别名: 2-Phenyl-benzo[b]thiophen-3-on；2-Phenyl-2,3-dihydro-1-benzothiophen-3-one；2-phenyl-1-benzothiophen-3-one
• CAS: 53614-69-0
• 化学式: C₁₄H₁₀OS
• 分子量: 226.299
• InChiKey: VWIXUROTJVJZOL-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  387.9±42.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-benzo[b]thiophen-3-one 、 乙醇 、 盐酸氨基脲 、 sodium acetate 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  v. Auwers; Thies, Chemische Berichte, 1920, vol. 53, p. 2296

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(2-benzylsulfanyl-benzoyl)-morpholine 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-phenyl-benzo[b]thiophen-3-one
  参考文献：
  名称：

  Potent, Selective, and Orally Available Benzoisothiazolone Phosphomannose Isomerase Inhibitors as Probes for Congenital Disorder of Glycosylation Ia

  摘要：

  We report the discovery and validation of a series of benzoisothiazolones as potent inhibitors of phosphomannose isomerase (PM), an enzyme that converts mannose-6-phosphate (Man-6-P) into fructose-6-phosphate (Fru-6-P) and, more importantly, competes with phosphomannomutase 2 (PMM2) for Man-6-P, diverting this substrate from critical protein glycosylation events. In congenital disorder of glycosylation type Ia, PMM2 activity is compromised.; thus, PMI inhibition is a potential strategy for the development of therapeutics. High-throughput screening (HTS) and subsequent chemical optimization led to the identification of a novel class of benzoisothiazolones as potent PMI inhibitors having little or no PMM2 inhibition. Two complementary synthetic routes were developed, enabling the critical structural requirements for activity to be determined, and the compounds were subsequently profiled in biochemical and cellular assays to assess efficacy. The most promising compounds were also profiled for bioavailability parameters, including metabolic stability, plasma stability, and permeability. The pharmacokinetic profile of a representative of this series (compound 19; ML089) was also assessed, demonstrating the potential of this series for in vivo efficacy when dosed orally in disease models.

  DOI：

  10.1021/jm101401a