(S)-7-(3-carboxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 957780-89-1

• 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: (S)-7-(3-carboxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-[(3S)-3-carboxy-3,4-dihydro-1H-isoquinolin-2-yl]-1-cyclopropyl-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 957780-89-1
• 化学式: C₂₃H₁₈FN₃O₇
• 分子量: 467.41
• InChiKey: BIEVGADNKODKFY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-7-(3-carboxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 在 sodium dithionite 、 potassium carbonate 作用下， 以53%的产率得到(S)-4-cyclopropyl-14-fluoro-1,6-dioxo-1,4,5,6,6a,7-hexahydro-12H-isoquinolino[2,3-a]pyrido[2,3-f]quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  Heterocycles [h]-Fused onto 4-oxoquinoline-3-carboxylic acid, III.1 Facile synthesis and antitumor activity of model heterocycles [a]-fused onto pyrido[2,3-f]quinoxaline-3-carboxylic acids

  摘要：

  Direct interaction between 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4oxo-1,4-dihydroquinoline-3-carboxylic acid and each of (S)-proline, (2S,4R)-4hydroxyproline and (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in hot aqueous ethanolic NaHCO3 yielded the corresponding optically pure N-(4-oxoquinolin-7-yl)-alpha-amino acids. The latter derivatives underwent reductive lactamization upon treatment with Na2S2O4 in aqueous ethanol to afford moderate yields of the respective pyrido[2,3-f]quinoxaline-3-carboxylic acid [fused]- to tetrahydropyrrolo[1,2-a]-, tetrahydrohydroxylpyrrolo [1,2-a] -and tetrahydroisoquinolino[2,3-a]heterocyclics 10-12, respectively. The antitumor activity against four human tumor cell lines showed that 10-12 displayed high levels of cytotoxicity as compared with Cisplatin. Interestingly, these compounds were more potent against breast carcinoma cell lines (MCF-7 and T-47D) than the lymphoid origin tumor cell lines (Jurkat and BHL-89). In particular, the (S)-proline derivative 10 exhibited preferential cytotoxicity to adherent cells (IC50 = 0.5 mu M), indicative of better potential in blocking the growth of solid tumors rather than the disseminated ones.

  DOI：

  10.1016/s0385-5414(07)81092-6
• 作为产物：
  描述：

  7-氯-1-环丙基-6-氟-8-硝基-4-氧代-1,4-二氢喹啉-3-羧酸 、 L-1,2,3,4-四氢异喹啉-3-羧酸盐酸盐 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以45%的产率得到(S)-7-(3-carboxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Heterocycles [h]-Fused onto 4-oxoquinoline-3-carboxylic acid, III.1 Facile synthesis and antitumor activity of model heterocycles [a]-fused onto pyrido[2,3-f]quinoxaline-3-carboxylic acids

  摘要：

  Direct interaction between 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4oxo-1,4-dihydroquinoline-3-carboxylic acid and each of (S)-proline, (2S,4R)-4hydroxyproline and (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in hot aqueous ethanolic NaHCO3 yielded the corresponding optically pure N-(4-oxoquinolin-7-yl)-alpha-amino acids. The latter derivatives underwent reductive lactamization upon treatment with Na2S2O4 in aqueous ethanol to afford moderate yields of the respective pyrido[2,3-f]quinoxaline-3-carboxylic acid [fused]- to tetrahydropyrrolo[1,2-a]-, tetrahydrohydroxylpyrrolo [1,2-a] -and tetrahydroisoquinolino[2,3-a]heterocyclics 10-12, respectively. The antitumor activity against four human tumor cell lines showed that 10-12 displayed high levels of cytotoxicity as compared with Cisplatin. Interestingly, these compounds were more potent against breast carcinoma cell lines (MCF-7 and T-47D) than the lymphoid origin tumor cell lines (Jurkat and BHL-89). In particular, the (S)-proline derivative 10 exhibited preferential cytotoxicity to adherent cells (IC50 = 0.5 mu M), indicative of better potential in blocking the growth of solid tumors rather than the disseminated ones.

  DOI：

  10.1016/s0385-5414(07)81092-6