Thymidinphosphordiamidat 3e | 56945-94-9

• 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: Thymidinphosphordiamidat 3e
• 英文别名: O^5'-diaminophosphoryl-thymidine；Thymidine 5'-phosphordiamidate；1-[(2R,4S,5R)-5-(diaminophosphoryloxymethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 56945-94-9
• 化学式: C₁₀H₁₇N₄O₆P
• 分子量: 320.242
• InChiKey: GGXNNWRBOBCCJD-XLPZGREQSA-N

物化性质

• 密度：
  1.545±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Thymidinphosphordiamidat 3e 在 盐酸 作用下， 反应 16.0h， 生成 胸苷酸
  参考文献：
  名称：

  Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture

  摘要：

  Thymidine 5'-phosphate (TMP) derivatives with masked phosphate groups were synthesized in tritiated form from [methyl-3H]thymidine. They were of interest as models for 5' nucleotide derivatives that might be able to permeate mammalian cells and then liberate intracellular antimetabolite 5' nucleotides by loss of the masking groups. Mouse L fibroblasts were grown in vitro in the presence of 1 mM 5'-amino-5'-deoxythymidine, which was found to suppress greater than 99% of cellular thymidine kinase activity while inhibiting the rate of cell division by only 30%. The TMP derivatives were less effective than thymidine in labeling the deoxyribonucleic acid (DNA) of the L cells. The labeling was inhibited 95-99% by 5'-amino-5'-deoxythymidine, indicating that it represented incorporation into DNA of [3H]thymidine formed from degradation of the test compounds. No evidence was obtained that the compounds acted as sources of intracellular TMP by cell permeation followed by loss of phosphate blocking groups. Similar studies yielded no evidence that the bis(m-nitrophenyl) ester of TMP produced intracellular TMP by that route in the LM(TK-) strain of L cells that are genetically deficient in thymidine kinase.

  DOI：

  10.1021/jm00378a036
• 作为产物：
  描述：

  beta-胸苷 在 磷酸三甲酯 、 ammonium hydroxide 、 三氯氧磷 作用下， 以52%的产率得到Thymidinphosphordiamidat 3e
  参考文献：
  名称：

  Preparation of 5-Fluoro- and 5-Alkyl-2′-deoxyuridine 5′-Phosphates free of 3′-Phosphates via Phosphorodiamidates

  摘要：

  DOI：

  10.1055/s-1982-29689

文献信息

• Preparation of 5-Fluoro- and 5-Alkyl-2′-deoxyuridine 5′-Phosphates free of 3′-Phosphates via Phosphorodiamidates
  作者：J. Ludwig、J. Tomasz

  DOI：10.1055/s-1982-29689

  日期：——
• Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture
  作者：Ram R. Chawla、Jerome J. Freed、Alexander Hampton

  DOI：10.1021/jm00378a036

  日期：1984.12

  Thymidine 5'-phosphate (TMP) derivatives with masked phosphate groups were synthesized in tritiated form from [methyl-3H]thymidine. They were of interest as models for 5' nucleotide derivatives that might be able to permeate mammalian cells and then liberate intracellular antimetabolite 5' nucleotides by loss of the masking groups. Mouse L fibroblasts were grown in vitro in the presence of 1 mM 5'-amino-5'-deoxythymidine, which was found to suppress greater than 99% of cellular thymidine kinase activity while inhibiting the rate of cell division by only 30%. The TMP derivatives were less effective than thymidine in labeling the deoxyribonucleic acid (DNA) of the L cells. The labeling was inhibited 95-99% by 5'-amino-5'-deoxythymidine, indicating that it represented incorporation into DNA of [3H]thymidine formed from degradation of the test compounds. No evidence was obtained that the compounds acted as sources of intracellular TMP by cell permeation followed by loss of phosphate blocking groups. Similar studies yielded no evidence that the bis(m-nitrophenyl) ester of TMP produced intracellular TMP by that route in the LM(TK-) strain of L cells that are genetically deficient in thymidine kinase.