10-dodecyl-8-fluoro-3-methyl-5-deazaflavin | 302897-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-dodecyl-8-fluoro-3-methyl-5-deazaflavin
• CAS: 302897-05-8
• 化学式: C₂₄H₃₂FN₃O₂
• 分子量: 413.535
• InChiKey: POLDLXWMZFJKOE-UHFFFAOYSA-N

物化性质

• 沸点：
  513.5±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  56.89
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-dodecyl-8-fluoro-3-methyl-5-deazaflavin 在 4 Angstroem MS 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 10-dodecyl-3-methyl-8-[N-methyl-N-[2-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate)ethyl]amino]-5-deazaflavin
  参考文献：
  名称：

  Synthesis and antitumor activities of novel 5-deazaflavin-sialic acid conjugate molecules

  摘要：

  6-Nitro-5-deazaflavin derivatives bearing O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha- and beta-D-galacto-non-2-ulopyranosylonate)alkyl group (sialosylalkyl group) at N(3) or N(10) and 8-amino-5-deazaflavin substituted with the sialosylalkyl group at the amino group were synthesized and their physicochemical properties as well as antitumor effects on KB and L1210 cells have been investigated. The configurations of the glycosides were determined by H-1 NMR and rate of hydrolysis of the glycosidic bond. It has been found that these conjugate molecules show significant antitumor activities. Combination of an 8-amino-5-deazaflavin with the sialosylalkyl group have been found to give rise to significant increase in antitumor activities of the compound. Antitumor effects of 6-nitro-5-deazaflavin-sialic acid conjugate molecules were similar or rather weak in comparison with those of the 6-nitro-5-deazaflavin derivatives without sialosylalkyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00124-3
• 作为产物：
  描述：

  2,4-二氟苯甲醛 、 6-(Dodecylamino)-3-methyluracil 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到10-dodecyl-8-fluoro-3-methyl-5-deazaflavin
  参考文献：
  名称：

  Synthesis and antitumor activities of novel 5-deazaflavin-sialic acid conjugate molecules

  摘要：

  6-Nitro-5-deazaflavin derivatives bearing O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha- and beta-D-galacto-non-2-ulopyranosylonate)alkyl group (sialosylalkyl group) at N(3) or N(10) and 8-amino-5-deazaflavin substituted with the sialosylalkyl group at the amino group were synthesized and their physicochemical properties as well as antitumor effects on KB and L1210 cells have been investigated. The configurations of the glycosides were determined by H-1 NMR and rate of hydrolysis of the glycosidic bond. It has been found that these conjugate molecules show significant antitumor activities. Combination of an 8-amino-5-deazaflavin with the sialosylalkyl group have been found to give rise to significant increase in antitumor activities of the compound. Antitumor effects of 6-nitro-5-deazaflavin-sialic acid conjugate molecules were similar or rather weak in comparison with those of the 6-nitro-5-deazaflavin derivatives without sialosylalkyl group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00124-3