Methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-2-(methylsulfanylmethyl)-1,2-oxazolidine-5-carboxylate | 1436712-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-2-(methylsulfanylmethyl)-1,2-oxazolidine-5-carboxylate
• 英文别名: methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-2-(methylsulfanylmethyl)-1,2-oxazolidine-5-carboxylate
• CAS: 1436712-88-7
• 化学式: C₂₀H₂₂BrNO₄S
• 分子量: 452.369
• InChiKey: YBECDCAMGRHYCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-2-(methylsulfanylmethyl)-1,2-oxazolidine-5-carboxylate 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以1.9 g的产率得到Methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-1,2-oxazolidine-5-carboxylate
  参考文献：
  名称：

  Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity

  摘要：

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.

  DOI：

  10.1021/jm3011349
• 作为产物：
  描述：

  3-溴-4'-甲氧基苯甲酮 在 吡啶 、 盐酸羟胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 0.67h， 生成 Methyl 3-(3-bromophenyl)-3-(4-methoxyphenyl)-2-(methylsulfanylmethyl)-1,2-oxazolidine-5-carboxylate
  参考文献：
  名称：

  Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity

  摘要：

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.

  DOI：

  10.1021/jm3011349