5-(2,6-dideoxy-2-fluoro-α-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-(2,6-dideoxy-2-fluoro-α-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione
• 英文别名: 5-(2,6-dideoxy-2-fluoro-α-L-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione；5-[(2S,3R,4R,5S,6S)-3-fluoro-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione
• 化学式: C₂₃H₁₈FNO₇
• 分子量: 439.397
• InChiKey: WPZUNLCLZODAEV-DQBGMDLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-羟基-4H-萘并[2,3-f]喹啉-6,7,12-三酮 在 甲醇 、 sodium methylate 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.0h， 生成 5-(2,6-dideoxy-2-fluoro-α-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione
  参考文献：
  名称：

  Preparation of 5-(2,6-dideoxy-2-fluoro-α-l-talopyranosyloxy)-6-hydroxynaphtho[2,3-f]quinoline-7,12-dione (FT-Alz), a new-type, potentially antitumor substance with various biological activities

  摘要：

  The title compound (6), its structure being imaginatively created, has been prepared through coupling of alizarine blue (2), a classical dye, and 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (3). Compound 6 has considerably higher and different antitumor activity from that of doxorubicin or its analogue (10), and, further, has properties to reverse multidrug resistance (by P-glycoprotein), to inhibit topoisomerase II, and to induce apoptosis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00655-1

文献信息

• 5-GLYCOSYLOXY-6-HYDROXYNAPHTHO 2,3-f]QUINOLINE-7,12-DIONE HAVING ANTICANCER ACTIVITIES
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP1156056A1

  公开（公告）日：2001-11-21

  As novel compounds which exhibit reduced toxicities but enhanced anticancer activities in comparison with those of known carcinostatic anthracycline derivatives, there is provided a compound of general formula (I) wherein A is methyl group or CF3 group, and B is hydrogen atom, or an electron-withdrawing group chosen from halogeno group and others, provided that B stands for hydrogen atom when A is CF3 and that B stands for an electron-withdrawing group when A is methyl group, and R1 and R2 each are hydroxyl group, amino group or an acyloxy group or an aminoalkanoyloxy group, and others, or a pharmaceutically acceptable salt thereof. The compound of general formula (I) possesses activities inhibitory to proliferation of various human cancer cells and is of lower toxicity than that of adriamycin. Further, there is provided, as novel and water-soluble carcinostatic compounds, a compound of general formula (V) wherein A and B have the same meanings as defined above, and R5 is hydrogen atom or an ω-amino acid residue, and R6 and R7 have the same meanings as defined for R5, provided that R5, R6 and R7 do not represent hydrogen atom, simultaneously.

  作为新型化合物，与已知的致癌性蒽环类衍生物相比，其毒性降低，但抗癌活性增强，现提供通式（I）的化合物 其中 A 为甲基或 CF3 基团，B 为氢原子或从卤代基团及其他基团中选出的抽电子基团，但 A 为 时 B 代表氢原子，A 为甲基时 B 代表抽电子基团，R1 和 R2 分别为羟基、氨基或酰氧基或氨基烷酰氧基及其他基团，或其药学上可接受的盐。通式（I）化合物具有抑制各种人类癌细胞增殖的活性，其毒性低于阿霉素。 此外，还提供了通式（V）化合物，作为新型水溶性抗癌化合物 其中 A 和 B 的含义与上述定义相同，R5 为氢原子或ω-氨基酸残基，R6 和 R7 的含义与 R5 的定义相同，但 R5、R6 和 R7 同时不代表氢原子。