(5S)-5-(aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one | 1093752-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5S)-5-(aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one
• CAS: 1093752-59-0
• 化学式: C₉H₁₀ClN₃O₂
• 分子量: 227.65
• InChiKey: POXHRRPXLATGBL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-(aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-[((5S)-2-oxo-3-{5-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1,3-oxazolidin-5-yl)methyl]benzamide
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27 mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.049
• 作为产物：
  描述：

  (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one 在 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5S)-5-(aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27 mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.049

文献信息

• CETP INHIBITORS DERIVED FROM BENZOXAZOLE ARYLAMIDES
  申请人：Hunt Julianne A.

  公开号：US20100184719A1

  公开（公告）日：2010-07-22

  Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

  具有公式I结构的化合物，包括化合物的药学上可接受的盐，是有效的CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。 在公式I中，A-B是芳香酰胺基团。
• CETP inhibitors derived from benzoxazole arylamides
  申请人：Merck Sharpe & Dohme Corp.

  公开号：US08293721B2

  公开（公告）日：2012-10-23

  Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

  具有I式结构的化合物，包括该化合物的药物可接受的盐，是有效的CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。在公式I中，A-B是芳基酰胺基团。
• WO2008/156718
  申请人：——

  公开号：——

  公开（公告）日：——
• US8293721B2
  申请人：——

  公开号：US8293721B2

  公开（公告）日：2012-10-23
• [EN] CETP INHIBITORS DERIVED FROM BENZOXAZOLE ARYLAMIDES<br/>[FR] INHIBITEURS DE CETP DÉRIVÉS DE BENZOXAZOLE ARYLAMIDES
  申请人：MERCK & CO INC

  公开号：WO2008156718A1

  公开（公告）日：2008-12-24

  [EN] Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.
  [FR] L'invention concerne des composés présentant une structure de formule I, ainsi que des sels acceptables sur le plan pharmaceutique desdits composés, qui sont de puissants inhibiteurs de CETP, qui sont utiles pour augmenter le HDL cholestérol, réduire le LDL cholestérol, et qui permettent de traiter ou de prévenir l'athérosclérose. Dans la formule I, A-B est un fragment arylamide.