t-Boc-Aib-FudR | 287731-67-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: t-Boc-Aib-FudR
• 英文别名: [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 287731-67-3
• 化学式: C₁₈H₂₆FN₃O₈
• 分子量: 431.418
• InChiKey: ZXRVJRXAGKZPQW-QJPTWQEYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  t-Boc-Aib-FudR 在 TEA 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-2-methylpropanoate
  参考文献：
  名称：

  Activation of antibacterial prodrugs by peptide deformylase

  摘要：

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00167-0
• 作为产物：
  描述：

  N-叔丁氧羰基-2-甲基丙氨酸 、 5-氟-2'-脱氧脲核苷 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 生成 t-Boc-Aib-FudR
  参考文献：
  名称：

  Activation of antibacterial prodrugs by peptide deformylase

  摘要：

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00167-0

文献信息

• A 5-fluorodeoxyuridine prodrug as targeted therapy for prostate cancer
  作者：Annastasiah Mhaka、Sam R Denmeade、Wei Yao、John T Isaacs、Saeed R Khan

  DOI：10.1016/s0960-894x(02)00433-x

  日期：2002.9

  A method for targeted delivery of the cytotoxic agent 5-fluorodeoxyuridine (FudR) (1) to sites of metastatic prostate cancer is described. The prodrug was synthesized by coupling the active drug (FudR) to the PSA-peptide via a self-cleaving diamino acid linker to produce HSSKLQ-Leu-Aib-FudR. This prodrug serves as a substrate for prostate specific antigen (PSA). This approach permitted efficient conversion of the inactive prodrug back to the active cytotoxic state by the enzymatic activity of PSA which is highly expressed by prostate cells. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Activation of antibacterial prodrugs by peptide deformylase
  作者：Yaoming Wei、Dehua Pei

  DOI：10.1016/s0960-894x(00)00167-0

  日期：2000.5

  5'-Dipeptidyl derivatives of 5-fluorodeoxyuridine (FdU) (1a-d) were synthesized. These compounds are biologically inactive but can be activated by peptide deformylase, which removes the N-terminal formyl group of the dipeptide, to release the active drug FdU via an intramolecular cyclization reaction. Because the deformylase is ubiquitous among bacteria but absent in mammalian cells, 1a-d provide a novel class of potential antibacterial agents. (C) 2000 Elsevier Science Ltd. All rights reserved.