5'-deoxysangivamycin | 65562-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-deoxysangivamycin
• 英文别名: 4-Amino-7-(3,4-dihydroxy-5-methyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid amide；4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 65562-56-3
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: HXTSROMHHXTVDO-BFAGERDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  桑霉素 在 吡啶 、 三丁基膦 、 镍 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 21.5h， 生成 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

文献信息

• An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin
  作者：Xiangyou Dong、Jie Tang、Chen Hu、Jiang Bai、Haixin Ding、Qiang Xiao

  DOI：10.3390/molecules24040737

  日期：——

  In present paper, an expeditious total synthesis of naturally occurring 5′-deoxytoyocamycin and 5′-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously

  在本文中，完成了天然存在的 5'-脱氧丰霉素和 5'-脱氧桑吉霉素的快速全合成。由于在 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine 的 N-6 处引入了苯甲酰基，因此与 1,2,3-tri-O-乙酰基的 Vorbrüggen 糖基化-5-脱氧-β-D-呋喃核糖提供了完全区域选择性的 N-9 糖基化产物，X 射线衍射分析明确证实了这一点。所有涉及的中间体都通过各种光谱进行了很好的表征。
• 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)
  作者：Tokumi Maruyama、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm00355a006

  日期：1983.1

  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.