10-Dodecyl-8-[2-hydroxyethyl(methyl)amino]-3-methylpyrimido[4,5-b]quinoline-2,4-dione | 302897-06-9

• 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-[2-hydroxyethyl(methyl)amino]-3-methylpyrimido[4,5-b]quinoline-2,4-dione
• 英文别名: 10-dodecyl-8-[2-hydroxyethyl(methyl)amino]-3-methylpyrimido[4,5-b]quinoline-2,4-dione
• CAS: 302897-06-9
• 化学式: C₂₇H₄₀N₄O₃
• 分子量: 468.64
• InChiKey: WXRHXNJYOULQHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 、 10-Dodecyl-8-[2-hydroxyethyl(methyl)amino]-3-methylpyrimido[4,5-b]quinoline-2,4-dione 在 4 Angstroem MS 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以22%的产率得到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-α-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 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 10-Dodecyl-8-[2-hydroxyethyl(methyl)amino]-3-methylpyrimido[4,5-b]quinoline-2,4-dione
  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

文献信息

• Synthesis and antitumor activities of novel 5-deazaflavin-sialic acid conjugate molecules
  作者：Yoshihiro Ikeuchi、Motoko Sumiya、Tetsuji Kawamoto、Naoshige Akimoto、Yuji Mikata、Maki Kishigami、Shigenobu Yano、Takuma Sasaki、Fumio Yoneda

  DOI：10.1016/s0968-0896(00)00124-3

  日期：2000.8

  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.