3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine | 1446526-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine
• CAS: 1446526-79-9
• 化学式: C₃₃H₃₅N₃O₆
• 分子量: 569.657
• InChiKey: ZNWXLNJDFJGHPF-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  111.65
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以69%的产率得到3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]thymidine
  参考文献：
  名称：

  3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition

  摘要：

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.047
• 作为产物：
  描述：

  3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 、 溴乙酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以92%的产率得到3'-deoxy-3'-N-[(ethoxycarbonyl)methylamino]-5'-O-tritylthymidine
  参考文献：
  名称：

  3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition

  摘要：

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.047