5'-deoxy-5'-(phenylthio)sangivamycin | 83379-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-deoxy-5'-(phenylthio)sangivamycin
• CAS: 83379-32-2
• 化学式: C₁₈H₁₉N₅O₄S
• 分子量: 401.446
• InChiKey: AIAFVINARDRRSL-XWXWGSFUSA-N

物化性质

• 沸点：
  784.2±70.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  149.51
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5'-(phenylthio)sangivamycin 在 镍 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以41%的产率得到5'-deoxysangivamycin
  参考文献：
  名称：

  Pyrrolopyrimidine nucleosides. 18, Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (2'-deoxysangivamycin)

  摘要：

  A multistep synthesis, using the nucleoside antibiotic toyocamycin as the starting material, has furnished 6,2'-S-cyclosangivamycin (6). Desulfurization of 6,2'-S-cyclosangivamycin (6) with Raney nickel has provided 2'-deoxysangivamycin (7). Treatment of sangivamycin (1c) with sodium iodide and alpha-acetoxyisobutyryl chloride has furnished 4-amino-7-[2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1, 3-dioxolan-2-yl)-beta-D-xylofuranosyl]-pyrrolo[2,3-d] pyrimidine-5-carboxamide (8a). Dehalogenation of 8a with 10% palladium on charcoal was followed by a removal of the blocking groups with ammonium hydroxide to give 3'-deoxysangivamycin (9) in 49% overall yield. The reaction of sangivamycin (1c) with diphenyl disulfide and tributylphosphine gave 5'-(phenylthio)-5'-deoxysangivamycin (10). Treatment of 10 with Raney Nickel afforded 5'-deoxysangivamycin (11). Antitumor evaluation showed that 3'-deoxysangivamycin had significant activity against the murine leukemia L1210 both in vivo and in vitro, although it was less potent on a molar basis than the parent compound sangivamycin. The 2'- and 5'-deoxysangivamycins did not show significant antitumor activity.

  DOI：

  10.1021/jm00355a006
• 作为产物：
  描述：

  桑霉素 、 二苯二硫醚 在 吡啶 、 三丁基膦 作用下， 反应 20.0h， 以68%的产率得到5'-deoxy-5'-(phenylthio)sangivamycin
  参考文献：
  名称：

  Pyrrolopyrimidine nucleosides. 18, Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (2'-deoxysangivamycin)

  摘要：

  A multistep synthesis, using the nucleoside antibiotic toyocamycin as the starting material, has furnished 6,2'-S-cyclosangivamycin (6). Desulfurization of 6,2'-S-cyclosangivamycin (6) with Raney nickel has provided 2'-deoxysangivamycin (7). Treatment of sangivamycin (1c) with sodium iodide and alpha-acetoxyisobutyryl chloride has furnished 4-amino-7-[2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1, 3-dioxolan-2-yl)-beta-D-xylofuranosyl]-pyrrolo[2,3-d] pyrimidine-5-carboxamide (8a). Dehalogenation of 8a with 10% palladium on charcoal was followed by a removal of the blocking groups with ammonium hydroxide to give 3'-deoxysangivamycin (9) in 49% overall yield. The reaction of sangivamycin (1c) with diphenyl disulfide and tributylphosphine gave 5'-(phenylthio)-5'-deoxysangivamycin (10). Treatment of 10 with Raney Nickel afforded 5'-deoxysangivamycin (11). Antitumor evaluation showed that 3'-deoxysangivamycin had significant activity against the murine leukemia L1210 both in vivo and in vitro, although it was less potent on a molar basis than the parent compound sangivamycin. The 2'- and 5'-deoxysangivamycins did not show significant antitumor activity.

  DOI：

  10.1021/jm00355a006