1-naphthyl-(methoxy-L-phenylglycinyl)phosphochloridate | 874362-17-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-naphthyl-(methoxy-L-phenylglycinyl)phosphochloridate
• 英文别名: (2S)-methyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate；methyl (2S)-2-[[chloro(naphthalen-1-yloxy)phosphoryl]amino]-2-phenylacetate
• CAS: 874362-17-1
• 化学式: C₁₉H₁₇ClNO₄P
• 分子量: 389.775
• InChiKey: NTSXYWJFAFZRRX-MDYZWHIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-naphthyl-(methoxy-L-phenylglycinyl)phosphochloridate 、 溴夫定 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以6.8%的产率得到(E)-5-(2-bromovinyl)-2'-deoxyuridine-5'-[1-naphthyl-(methoxy-L-phenylglycinyl)]phosphate
  参考文献：
  名称：

  Novel Potential Anticancer Naphthyl Phosphoramidates of BVdU:  Separation of Diastereoisomers and Assignment of the Absolute Configuration of the Phosphorus Center

  摘要：

  We have previously reported our SAR optimization of the anticancer agent thymectacin. Tuning of the parent ProTide structure initially involved the amino acid and, subsequently, the aromatic masking group on the phosphate moiety. Herein, derivatives bearing the combined modifications are reported and biological evaluation is described. Moreover, separation of the diastereoisomeric final product mixture shows a different cytostatic activity for the two diastereoisomers. Through computational and NMR studies, the absolute stereochemistry of the phosphorus center of the two diastereoisomers has been suggested.

  DOI：

  10.1021/jm0509896
• 作为产物：
  描述：

  1-萘基二氯磷酸酯 、 甲基2-(苯基氨基)乙酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-naphthyl-(methoxy-L-phenylglycinyl)phosphochloridate
  参考文献：
  名称：

  Novel Potential Anticancer Naphthyl Phosphoramidates of BVdU:  Separation of Diastereoisomers and Assignment of the Absolute Configuration of the Phosphorus Center

  摘要：

  We have previously reported our SAR optimization of the anticancer agent thymectacin. Tuning of the parent ProTide structure initially involved the amino acid and, subsequently, the aromatic masking group on the phosphate moiety. Herein, derivatives bearing the combined modifications are reported and biological evaluation is described. Moreover, separation of the diastereoisomeric final product mixture shows a different cytostatic activity for the two diastereoisomers. Through computational and NMR studies, the absolute stereochemistry of the phosphorus center of the two diastereoisomers has been suggested.

  DOI：

  10.1021/jm0509896

文献信息

• Phosphoramidate Derivatives of Guanosine Nucleoside Compunds for Treatment of Viral Infections
  申请人：Chamberlain Stanley

  公开号：US20120052046A1

  公开（公告）日：2012-03-01

  Phosphoramidate compounds derived from guanine bases having enhanced therapeutic potency are provided, and these compounds in particular have enhanced potency with respect to treatment of viral infections, such as hepatitis C virus. Pharmaceutical compositions, methods of preparing the compounds, and methods of using the compounds and compositions to treat viral infections are also provided.

  本发明提供了从鸟嘌呤碱基衍生的磷酰胺化合物，具有增强的治疗效力，特别是对于治疗病毒感染，如丙型肝炎病毒，具有增强的效力。本发明还提供了制备该化合物的制药组合物、制备该化合物的方法以及使用该化合物和组合物治疗病毒感染的方法。
• PHOSPHORAMIDATE DERIVATIVES OF GUANOSINE NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS
  申请人：University College Cardiff Consultants, Ltd.

  公开号：EP2385951A2

  公开（公告）日：2011-11-16
• US8759318B2
  申请人：——

  公开号：US8759318B2

  公开（公告）日：2014-06-24
• [EN] PHOSPHORAMIDATE DERIVATIVES OF GUANOSINE NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS<br/>[FR] DÉRIVÉS DE PHOSPHORAMIDATE DE COMPOSÉS GUANOSINE NUCLÉOSIDE POUR LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：UNIV CARDIFF

  公开号：WO2010081082A2

  公开（公告）日：2010-07-15

  Phosphoramidate compounds derived from guanine bases having enhanced therapeutic potency are provided, and these compounds in particular have enhanced potency with respect to treatment of viral infections, such as hepatitis C virus. Pharmaceutical compositions, methods of preparing the compounds, and methods of using the compounds and compositions to treat viral infections are also provided.
• Novel Potential Anticancer Naphthyl Phosphoramidates of BVdU:  Separation of Diastereoisomers and Assignment of the Absolute Configuration of the Phosphorus Center
  作者：Costantino Congiatu、Andrea Brancale、Malcolm D. Mason、Wen G. Jiang、Christopher McGuigan

  DOI：10.1021/jm0509896

  日期：2006.1.1

  We have previously reported our SAR optimization of the anticancer agent thymectacin. Tuning of the parent ProTide structure initially involved the amino acid and, subsequently, the aromatic masking group on the phosphate moiety. Herein, derivatives bearing the combined modifications are reported and biological evaluation is described. Moreover, separation of the diastereoisomeric final product mixture shows a different cytostatic activity for the two diastereoisomers. Through computational and NMR studies, the absolute stereochemistry of the phosphorus center of the two diastereoisomers has been suggested.