(2S)-isopropyl 2-(((2-chloro-4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate | 1334513-04-0

• 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: (2S)-isopropyl 2-(((2-chloro-4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate
• 英文别名: (2S)-isopropyl 2-(((S)-(2-chloro-4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate；(S)-2-[(S)-(2-chloro-4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester；propan-2-yl (2S)-2-[[(2-chloro-4-nitrophenoxy)-phenoxyphosphoryl]amino]propanoate
• CAS: 1334513-04-0
• 化学式: C₁₈H₂₀ClN₂O₇P
• 分子量: 442.793
• InChiKey: WUCRTWFQWCNWDL-YBKRRLQSSA-N

物化性质

• 熔点：
  70-72 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  530.4±60.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-isopropyl 2-(((2-chloro-4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate 、 2',3'-异丙叉腺苷 在 叔丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.55h， 生成 isopropyl ((S)-(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
  参考文献：
  名称：

  Synthesis of Diastereomerically Pure Nucleotide Phosphoramidates

  摘要：

  Prodrugs of therapeutic nucleoside monophosphates masked as phosphoramidate derivatives have become an increasingly important class of antiviral drugs in pharmaceutical research for delivering nucleotides in vitro and in vivo. Conventionally, phosphoramidate derivatives are prepared as a mixture of two diastereomers. We report a class of stable phosphoramidating reagents containing an amino acid ester and two phenolic groups, one unsubstituted and the other with electron-withdrawing substituents. The reagents can be isolated as single diastereomers and reacted with the 5'-hydroxyl group of nucleosides through selective nucleophilic displacement of the substituted phenol to prepare single diastereomer phosphoramidate products. This method has been used to prepare the HCV clinical candidate PSI-7977 in high yield and high diastereomeric purity.

  DOI：

  10.1021/jo201492m
• 作为产物：
  描述：

  二氯磷酸苯酯 在 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.5h， 生成 (2S)-isopropyl 2-(((2-chloro-4-nitrophenoxy)(phenoxy)phosphoryl)amino)propanoate
  参考文献：
  名称：

  [EN] NUCLEOTIDE AND NUCLEOSIDE COMPOSITIONS AND USES RELATED THERETO
  [FR] COMPOSITIONS À BASE DE NUCLÉOTIDE ET DE NUCLÉOSIDE ET UTILISATIONS CORRESPONDANTES

  摘要：

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，在这些组合物中，核苷酸或核苷的碱基至少含有一个硫醇、硫酮或硫醚。

  公开号：

  WO2015038596A1

文献信息

• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOTIDES ET NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2017155923A1

  公开（公告）日：2017-09-14

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，在这些组合物中，核苷酸或核苷的碱基至少含有一个硫醇、硫酮或硫醚。
• [EN] ALKYNE CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOTIDES ET NUCLÉOSIDES CONTENANT UN ALCYNE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2017189978A1

  公开（公告）日：2017-11-02

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，其中核苷酸或核苷的碱基至少含有一个硫醇、硫酮或硫醚。
• [EN] PHOSPHORAMIDATES FOR THE TREATMENT OF HEPATITIS B VIRUS<br/>[FR] PHOSPHORAMIDATES POUR LE TRAITEMENT DU VIRUS DE L'HÉPATITE B
  申请人：UNIV EMORY

  公开号：WO2017223421A1

  公开（公告）日：2017-12-28

  Disclosed are compounds and compositions to the treatment of infectious diseases and methods of treating such diseases. The compounds and compositions include derivatives of clevudine. The compounds and compositions include derivatives of clevudine in combination with another antiviral agent. The compounds and compositions include derivatives of clevudine in combination with a phosphoramidate of lamivudine, adefovir, tenofovir, telbivudine, entecavir, or combinations thereof.

  揭示了用于治疗传染病的化合物和组合物，以及治疗此类疾病的方法。这些化合物和组合物包括克鲁地宁��衍生物。这些化合物和组合物包括克鲁地宁的衍生物与另一种抗病毒药物的组合。这些化合物和组合物包括克鲁地宁的衍生物与拉米夫定的磷酰胺、阿德福韦、替诺福韦、替比韦定、恩替卡韦或它们的组合物的组合。
• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTICS COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES RENFERMANT DES NUCLÉOTIDES ET DES NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2016145142A1

  公开（公告）日：2016-09-15

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这份披露涉及到核苷酸和核苷类治疗组合物，用于治疗传染病、病毒感染和癌症，其中核苷酸或核苷的碱基至少含有一个硫醇、硫醌或硫醚。
• [EN] NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES RENFERMANT DES NUCLÉOTIDES ET DES NUCLÉOSIDES ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2017106710A1

  公开（公告）日：2017-06-22

  This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

  这项披露涉及核苷酸和核苷治疗组合物及其在治疗传染病、病毒感染和癌症中的用途，其中核苷酸或核苷的碱基至少含有一个硫醇、硫醌或硫醚。