4-{[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}benzaldehyde | 1095989-51-7

• 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: 4-{[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}benzaldehyde
• 英文别名: 4-{[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl} benzaldehyde；4-[[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl]benzaldehyde
• CAS: 1095989-51-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ARDVQXUARAKENO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基环己胺 、 4-{[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}benzaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-3-(4-((cyclohexyl(methyl)amino)methyl)benzyl)-5-methyloxazolidin-2-one
  参考文献：
  名称：

  3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization

  摘要：

  The discovery, synthesis and SAR of a novel series of 3-benzyl-1,3-oxazolidin-2-ones as positive allosteric modulators (PAMs) of mGluR2 is described. Expedient hit-to-lead work on a single HTS hit led to the identification of a ligand-efficient and structurally attractive series of mGluR2 PAMs. Human microsomal clearance and suboptimal physicochemical properties of the initial lead were improved to give potent, metabolically stable and orally available mGluR2 PAMs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.032
• 作为产物：
  描述：

  (5R)-3-[4-(1,3-dioxolan-2-yl)benzyl]-5-methyl-1,3-oxazolidin-2-one 在 硫酸 碳酸氢钠 、 silica gel 、 ethyl acetate heptane 作用下， 以 丙酮 、 乙酸乙酯 为溶剂， 反应 1.5h， 以provided 230 mg of the title compound as a colorless oil的产率得到4-{[(5R)-5-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}benzaldehyde
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS

  摘要：

  本文披露了化合物及其药学上可接受的盐，其中化合物具有规范中定义的I式结构。还披露了相应的药物组合物、治疗方法、合成方法和中间体。

  公开号：

  US20090137577A1

文献信息

• [EN] N-BENZYL OXAZOLIDINONES AND RELATED HETEROCYCLEIC COMPOUNDS AS POTENTIATORS OF GLUTAMATE RECEPTORS<br/>[FR] N-BENZYL OXAZOLIDINONES ET COMPOSÉS HÉTÉROCYCLIQUES APPARENTÉS COMME POTENTIALISATEURS DE RÉCEPTEURS DU GLUTAMATE
  申请人：PFIZER

  公开号：WO2009004430A1

  公开（公告）日：2009-01-08

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed. The compounds are active as potentiators of glutamate receptors, in particular mGluR2.

  本发明揭示了化合物及其在规范中定义的Formula（I）结构的药学上可接受的盐，相应的药物组合物、治疗方法、合成方法和中间体也被揭示。这些化合物作为谷氨酸受体的增强剂活性，特别是mGluR2。
• 3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization
  作者：Allen J. Duplantier、Ivan Efremov、John Candler、Angela C. Doran、Alan H. Ganong、Jessica A. Haas、Ashley N. Hanks、Kenneth G. Kraus、John T. Lazzaro、Jiemin Lu、Noha Maklad、Sheryl A. McCarthy、Theresa J. O’Sullivan、Bruce N. Rogers、Judith A. Siuciak、Douglas K. Spracklin、Lei Zhang

  DOI：10.1016/j.bmcl.2009.03.032

  日期：2009.5

  The discovery, synthesis and SAR of a novel series of 3-benzyl-1,3-oxazolidin-2-ones as positive allosteric modulators (PAMs) of mGluR2 is described. Expedient hit-to-lead work on a single HTS hit led to the identification of a ligand-efficient and structurally attractive series of mGluR2 PAMs. Human microsomal clearance and suboptimal physicochemical properties of the initial lead were improved to give potent, metabolically stable and orally available mGluR2 PAMs. (C) 2009 Elsevier Ltd. All rights reserved.
• HETEROCYCLIC COMPOUNDS
  申请人：Duplantier Allen J.

  公开号：US20090137577A1

  公开（公告）日：2009-05-28

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本文披露了化合物及其药学上可接受的盐，其中化合物具有规范中定义的I式结构。还披露了相应的药物组合物、治疗方法、合成方法和中间体。