4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide | 83379-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide
• 英文别名: 4-amino-7-[2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl]pyrrolo[2,3-d]pyrimidine-5-carboxamide；[(2R,3S,4S,5R)-2-(4-amino-5-carbamoylpyrrolo[2,3-d]pyrimidin-7-yl)-4-iodo-5-[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 83379-29-7
• 化学式: C₂₀H₂₄IN₅O₈
• 分子量: 589.344
• InChiKey: DJRGDRXRAUQHGJ-NBPRPYEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  180.11
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以49%的产率得到3'-脱氧桑吉瓦霉素
  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：

  2-乙酰氧基异丁酰氯 、 桑霉素 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以56%的产率得到4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide
  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