3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic acid | 1360861-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic acid
• 英文别名: 3-[(3,5,6,7,8-Pentafluoro-1,4-dioxonaphthalen-2-yl)amino]propanoic acid；3-[(3,5,6,7,8-pentafluoro-1,4-dioxonaphthalen-2-yl)amino]propanoic acid
• CAS: 1360861-73-9
• 化学式: C₁₃H₆F₅NO₄
• 分子量: 335.187
• InChiKey: IYLZTGLONDPRJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以100%的产率得到3-(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)propanoyl chloride
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of polyfluorinated 1,4-naphthoquinones containing amino acid substituents

  摘要：

  New conjugates of polyfluorinated 1,4-naphthoquinone core with amino acid fragments were synthesized by the reactions of hexafluoro-1,4-naphthoquinone (1) with ethyl aminoacetate, glycine, 3-aminopropanoic, 4-aminobutanoic, and 6-aminohexanoic acids. In all the cases, the quinone 1-aminodefluorination on the 2-position occurred to give ethyl (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminoacetate (2), (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminolacetic (3), 3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic (4), 4-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]butanoic (5), and 6-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]hexanoic acid (6), respectively. A possibility to further modify a carboxylic function of omega-[5,6,7,8-tetrafluoro-1,4-naphthoquinon-2-yl]aminocarboxylic acids was demonstrated by transformation of acids 3 and 5 into the corresponding acyl chlorides 10 and 12 followed by their in situ conversion into N,N-diethylamides 13 and 14 or ethyl esters 15 and 16. Upon the analogous treatment of acid 4 the primary generated acyl chloride 11 underwent an intramolecular N-acylation to yield 2,5,6,7,8-pentafluoro-3-(2-oxopyrrolidin-1-yl)naphthalene-1,4-dione (17) which was smoothly diethylaminodefluorinated at the 3-position to afford 2-(2-oxopyrrolidin-1-yl)-3-diethylamino-5,6,7,8-tetrafluoronaphthalene-1,4-dione (18). The cytotoxicity evaluation of twelve new quinones in human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells as well as their mutagenic and antioxidant properties in a Salmonella tester strain was performed. All the compounds effectively suppressed the growth of three lines of tumor cells. These data together with the better cytotoxic effect against cancer cells compared to normal mammalian cells, the bacterial cells protection against spontaneous and H2O2-dependent mutagenesis, and lower general toxicity toward different cells, reveal quinones 2, 13, 15, 16, and 18 as best inhibitors of tumor cells growth among the tested substances. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.04.014
• 作为产物：
  描述：

  hexafluoro-1,4-naphthoquinone 、 β-丙氨酸 以 1,4-二氧六环 为溶剂， 反应 360.0h， 以80%的产率得到3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of polyfluorinated 1,4-naphthoquinones containing amino acid substituents

  摘要：

  New conjugates of polyfluorinated 1,4-naphthoquinone core with amino acid fragments were synthesized by the reactions of hexafluoro-1,4-naphthoquinone (1) with ethyl aminoacetate, glycine, 3-aminopropanoic, 4-aminobutanoic, and 6-aminohexanoic acids. In all the cases, the quinone 1-aminodefluorination on the 2-position occurred to give ethyl (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminoacetate (2), (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminolacetic (3), 3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic (4), 4-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]butanoic (5), and 6-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]hexanoic acid (6), respectively. A possibility to further modify a carboxylic function of omega-[5,6,7,8-tetrafluoro-1,4-naphthoquinon-2-yl]aminocarboxylic acids was demonstrated by transformation of acids 3 and 5 into the corresponding acyl chlorides 10 and 12 followed by their in situ conversion into N,N-diethylamides 13 and 14 or ethyl esters 15 and 16. Upon the analogous treatment of acid 4 the primary generated acyl chloride 11 underwent an intramolecular N-acylation to yield 2,5,6,7,8-pentafluoro-3-(2-oxopyrrolidin-1-yl)naphthalene-1,4-dione (17) which was smoothly diethylaminodefluorinated at the 3-position to afford 2-(2-oxopyrrolidin-1-yl)-3-diethylamino-5,6,7,8-tetrafluoronaphthalene-1,4-dione (18). The cytotoxicity evaluation of twelve new quinones in human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells as well as their mutagenic and antioxidant properties in a Salmonella tester strain was performed. All the compounds effectively suppressed the growth of three lines of tumor cells. These data together with the better cytotoxic effect against cancer cells compared to normal mammalian cells, the bacterial cells protection against spontaneous and H2O2-dependent mutagenesis, and lower general toxicity toward different cells, reveal quinones 2, 13, 15, 16, and 18 as best inhibitors of tumor cells growth among the tested substances. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.04.014

文献信息

• Synthesis and cytotoxicity evaluation of polyfluorinated 1,4-naphthoquinones containing amino acid substituents
  作者：N.M. Troshkova、L.I. Goryunov、V.D. Shteingarts、O.D. Zakharova、L.P. Ovchinnikova、G.A. Nevinsky

  DOI：10.1016/j.jfluchem.2014.04.014

  日期：2014.8

  New conjugates of polyfluorinated 1,4-naphthoquinone core with amino acid fragments were synthesized by the reactions of hexafluoro-1,4-naphthoquinone (1) with ethyl aminoacetate, glycine, 3-aminopropanoic, 4-aminobutanoic, and 6-aminohexanoic acids. In all the cases, the quinone 1-aminodefluorination on the 2-position occurred to give ethyl (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminoacetate (2), (3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)aminolacetic (3), 3-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]propanoic (4), 4-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]butanoic (5), and 6-[(3,5,6,7,8-pentafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino]hexanoic acid (6), respectively. A possibility to further modify a carboxylic function of omega-[5,6,7,8-tetrafluoro-1,4-naphthoquinon-2-yl]aminocarboxylic acids was demonstrated by transformation of acids 3 and 5 into the corresponding acyl chlorides 10 and 12 followed by their in situ conversion into N,N-diethylamides 13 and 14 or ethyl esters 15 and 16. Upon the analogous treatment of acid 4 the primary generated acyl chloride 11 underwent an intramolecular N-acylation to yield 2,5,6,7,8-pentafluoro-3-(2-oxopyrrolidin-1-yl)naphthalene-1,4-dione (17) which was smoothly diethylaminodefluorinated at the 3-position to afford 2-(2-oxopyrrolidin-1-yl)-3-diethylamino-5,6,7,8-tetrafluoronaphthalene-1,4-dione (18). The cytotoxicity evaluation of twelve new quinones in human myeloma, human mammary adenocarcinoma, human hepatocellular carcinoma HepG2 epithelial tumor cells, normal mouse fibroblasts and Chinese hamster Ag 17 cells as well as their mutagenic and antioxidant properties in a Salmonella tester strain was performed. All the compounds effectively suppressed the growth of three lines of tumor cells. These data together with the better cytotoxic effect against cancer cells compared to normal mammalian cells, the bacterial cells protection against spontaneous and H2O2-dependent mutagenesis, and lower general toxicity toward different cells, reveal quinones 2, 13, 15, 16, and 18 as best inhibitors of tumor cells growth among the tested substances. (C) 2014 Elsevier B.V. All rights reserved.