2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-methyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one | 581104-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-methyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(6-methyl-5-oxo-3-sulfanylidene-1,2,4-triazin-2-yl)oxan-2-yl]methyl acetate
• CAS: 581104-38-3
• 化学式: C₁₈H₂₃N₃O₁₀S
• 分子量: 473.461
• InChiKey: CZBDJXNEWVGDTL-RUCLQGLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-methyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 反应 0.67h， 以87%的产率得到3,2'-anhydro-2-(3,4,6-tri-O-acetyl-β-D-talosyl)-3-mercapto-1,2,4-triazin-5(2H)-one
  参考文献：
  名称：

  A novel simple pyrolytic approach towards anhydronucleosides

  摘要：

  An interesting novel gas phase thermal intramolecular substitution reaction was discovered which led to the conversion of the 2-beta-D-N-glucosyl. 2-beta-D-N-Plactosyl and 2-beta-D-N-ribosyl derivatives of 3-thioxo-2.3-dihydro-1.2.4-triazin-5(4H)-ones into their corresponding 3,2'-anhydro-beta-D-marmosyl, 3,2'-anhydro-beta-D-talosyl and 3,2'-anhydro-beta-D-arabinosyl derivatives. The structures of these new anhydroglycosyls were determined by NMR experiments and by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.050
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-methyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  Selective Synthesis and Reactions of 6-Substituted- 2-β-galactosyl-1,2,4-triazines of Potential Anticancer Activity

  摘要：

  Selective synthesis and reactions of different 6-substituted-2-beta-D-galactosyl-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones using the developed amino or aryl protecting group strategy were investigated. Primary human anticancer screening of twelve selected compounds (in vitro) resulted in an active compound against both MCF7 (Breast) and SF-268(CNS) cell lines.

  DOI：

  10.1081/ncn-120018621