6-(dimethylamino)-9-(3'-amino-5'-chloro-3',5'-dideoxy-β-D-ribofuranosyl)purine | 80361-98-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 6-(dimethylamino)-9-(3'-amino-5'-chloro-3',5'-dideoxy-β-D-ribofuranosyl)purine
• CAS: 80361-98-4
• 化学式: C₁₂H₁₇ClN₆O₂
• 分子量: 312.759
• InChiKey: JMOGPPMFXMKROZ-GRIPGOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  102.32
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-(dimethylamino)-9-(3'-amino-5'-chloro-3',5'-dideoxy-β-D-ribofuranosyl)purine 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.13h， 生成 5'-chloro-5'-deoxypuromycin
  参考文献：
  名称：

  5'-Chloropuromycin. Inhibition of protein synthesis and antitrypanosomal activity

  摘要：

  A facile, two-step conversion of puromycin aminonucleoside (PAN) into 5'-deoxy-PAN (5) via 5'-chloro-5'-deoxy-PAN (1) was accomplished. Replacement of the 5'-OH group of PAN with H or Cl resulted in the elimination of kidney toxicity associated with the administration of PAN. The corresponding puromycin derivatives, 5'-chloro-5'-deoxypuromycin (4) and 5'-deoxypuromycin (6), derived from 1 and 5, respectively, were compared in a ribosomal peptidyltransferase assay. Both compounds were excellent substrates for the transpeptidation reaction, confirming our previous observations with 6 that the 5'-OH of puromycin is not essential for activity at the ribosomal level. Thus, 4 represents a new puromycin derivative that retains puromycin-like activity at the ribosomal site but is capable of releasing only a nonnephrotoxic aminonucleoside upon enzymatic release of the p-methoxyphenylalanyl side chain. The chloro derivative 4 exhibited significant antitrypanosomal activity in mice infected with Trypanosoma rhodesiense. The 5'-deoxy derivative 6 was inactive against trypanosomes.

  DOI：

  10.1021/jm00144a027
• 作为产物：
  描述：

  氨基核苷嘌呤霉素 在 氯化亚砜 、 磷酸三乙酯 作用下， 反应 14.0h， 以74%的产率得到6-(dimethylamino)-9-(3'-amino-5'-chloro-3',5'-dideoxy-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  5'-Chloropuromycin. Inhibition of protein synthesis and antitrypanosomal activity

  摘要：

  A facile, two-step conversion of puromycin aminonucleoside (PAN) into 5'-deoxy-PAN (5) via 5'-chloro-5'-deoxy-PAN (1) was accomplished. Replacement of the 5'-OH group of PAN with H or Cl resulted in the elimination of kidney toxicity associated with the administration of PAN. The corresponding puromycin derivatives, 5'-chloro-5'-deoxypuromycin (4) and 5'-deoxypuromycin (6), derived from 1 and 5, respectively, were compared in a ribosomal peptidyltransferase assay. Both compounds were excellent substrates for the transpeptidation reaction, confirming our previous observations with 6 that the 5'-OH of puromycin is not essential for activity at the ribosomal level. Thus, 4 represents a new puromycin derivative that retains puromycin-like activity at the ribosomal site but is capable of releasing only a nonnephrotoxic aminonucleoside upon enzymatic release of the p-methoxyphenylalanyl side chain. The chloro derivative 4 exhibited significant antitrypanosomal activity in mice infected with Trypanosoma rhodesiense. The 5'-deoxy derivative 6 was inactive against trypanosomes.

  DOI：

  10.1021/jm00144a027