phenyl benzylalanyl phosphorochloridate

• 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: phenyl benzylalanyl phosphorochloridate
• 英文别名: Benzyl 2-[[chloro(phenoxy)phosphoryl]amino]propanoate；benzyl 2-[[chloro(phenoxy)phosphoryl]amino]propanoate
• 化学式: C₁₆H₁₇ClNO₄P
• 分子量: 353.742
• InChiKey: AOZOBLLGZPZKKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  、 phenyl benzylalanyl phosphorochloridate 在 phenyl benzylalanyl phosphorochloridate 作用下， 以85的产率得到
  参考文献：
  名称：

  [EN] CHEMICAL COMPOUNDS
  [FR] COMPOSES CHIMIQUES

  摘要：

  本文描述了核苷酸的磷酰胺衍生物及其在癌症治疗中的应用。例如，脱氧尿嘧啶，阿糖胞苷，吉西他滨和胞苷的碱基部分可以在5位位置上被替代。磷酰胺基团附着在P原子上，其中有一个芳基-O基团和一个α-氨基酸基团。α-氨基酸基团可以对应于或派生自天然存在或非天然存在的氨基酸。

  公开号：

  WO2005012327A2
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)alanine benzyl ester 在 TEA 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 phenyl benzylalanyl phosphorochloridate
  参考文献：
  名称：

  6-Hydrazinopurine 2′-methyl ribonucleosides and their 5′-monophosphate prodrugs as potent hepatitis C virus inhibitors

  摘要：

  A series of 6-hydrazinopurine 2 '-methyl ribonucleosides was synthesized and tested for its inhibitory activity against the hepatitis C virus (HCV). The lack of antiviral activity of these nucleosides was associated with a poor affinity for adenosine kinase, which prompted us to synthesize several of their 5 '-monophosphate prodrugs. Some of these prodrugs exhibited more than 1000-fold improvement in anti-HCV activity when compared to their parent nucleosides (EC50 of 24 mu M vs 92 mu M for the parent). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.029
• 作为试剂：
  描述：

  、 phenyl benzylalanyl phosphorochloridate 在 phenyl benzylalanyl phosphorochloridate 作用下， 以85的产率得到
  参考文献：
  名称：

  J. Med. Chem. 2014, 57, 1531-1542

  摘要：

  DOI：

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：UNIV CARDIFF

  公开号：WO2005012327A2

  公开（公告）日：2005-02-10

  Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The α-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.

  本文描述了核苷酸的磷酰胺衍生物及其在癌症治疗中的应用。例如，脱氧尿嘧啶，阿糖胞苷，吉西他滨和胞苷的碱基部分可以在5位位置上被替代。磷酰胺基团附着在P原子上，其中有一个芳基-O基团和一个α-氨基酸基团。α-氨基酸基团可以对应于或派生自天然存在或非天然存在的氨基酸。
• Phosphoramidate derivatives of 2′,3′-didehydro-2′,3′-dideoxyadenosine [d4A] have markedly improved anti-HIV potency and selectivity
  作者：Christopher McGuigan、Orson M. Wedgwood、Erik De Clercq、Jan Balzarini

  DOI：10.1016/0960-894x(96)00433-7

  日期：1996.10

  New 5'-phosphate derivatives of the nucleoside analogue d4A were prepared as potential membrane-soluble prodrugs of the free nucleotide. The anti-viral potency and selectivity of the derivatives is markedly increased by comparison to the parent nucleoside analogue. The new analogues show particular promise for further pre-clinical development. Copyright (C) 1996 Elsevier Science Ltd
• PROCESS FOR THE PREPARATION OF GEMCITABINE-[PHENYL(BENZOXY-L-ALANINYL)] PHOSPHATE
  申请人：NuCana Biomed Limited

  公开号：US20170166602A1

  公开（公告）日：2017-06-15

  The present invention provides a process for the preparation of gemcitabine-[phenyl(benzoxy-L-alaninyl)] phosphate of Formula I in high yield and purity.
• US9834577B2
  申请人：——

  公开号：US9834577B2

  公开（公告）日：2017-12-05
• 6-Hydrazinopurine 2′-methyl ribonucleosides and their 5′-monophosphate prodrugs as potent hepatitis C virus inhibitors
  作者：Esmir Gunic、Suetying Chow、Frank Rong、Kanda Ramasamy、Anneke Raney、David Yunzhi Li、Jingfan Huang、Robert K. Hamatake、Zhi Hong、Jean-Luc Girardet

  DOI：10.1016/j.bmcl.2007.02.029

  日期：2007.5

  A series of 6-hydrazinopurine 2 '-methyl ribonucleosides was synthesized and tested for its inhibitory activity against the hepatitis C virus (HCV). The lack of antiviral activity of these nucleosides was associated with a poor affinity for adenosine kinase, which prompted us to synthesize several of their 5 '-monophosphate prodrugs. Some of these prodrugs exhibited more than 1000-fold improvement in anti-HCV activity when compared to their parent nucleosides (EC50 of 24 mu M vs 92 mu M for the parent). (C) 2007 Elsevier Ltd. All rights reserved.