2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-(trans-β-(4-chlorophenyl)vinyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one | 581104-47-4

• 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-(trans-β-(4-chlorophenyl)vinyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one
• CAS: 581104-47-4
• 化学式: C₂₅H₂₆ClN₃O₁₀S
• 分子量: 596.015
• InChiKey: UYVPBOFNNZFSNT-BGFJQOMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  165.11
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-(trans-β-(4-chlorophenyl)vinyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 、 碘甲烷 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{6-[(E)-2-(4-chloro-phenyl)-vinyl]-5-methoxy-3-thioxo-3H-[1,2,4]triazin-2-yl}-tetrahydro-pyran-3-yl ester 、 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{6-[(E)-2-(4-chloro-phenyl)-vinyl]-4-methyl-5-oxo-3-thioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl}-tetrahydro-pyran-3-yl ester 、 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{6-[(E)-2-(4-chloro-phenyl)-vinyl]-3-methylsulfanyl-5-oxo-5H-[1,2,4]triazin-2-yl}-tetrahydro-pyran-3-yl ester
  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
• 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-(trans-β-(4-chlorophenyl)vinyl)-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