3-{[4-(2-hydroxyethyl)phenyl]amino}-1,4-dioxo-1,4-dihydronaphthalene-2-carboxylic acid | 1387566-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-{[4-(2-hydroxyethyl)phenyl]amino}-1,4-dioxo-1,4-dihydronaphthalene-2-carboxylic acid
• 英文别名: 3-[4-(2-hydroxyethyl)anilino]-1,4-dioxonaphthalene-2-carboxylic acid
• CAS: 1387566-84-8
• 化学式: C₁₉H₁₅NO₅
• 分子量: 337.332
• InChiKey: LMBCMMMWUONXKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  103.7
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,4-二羟基-2-萘甲酸 、 4-氨基苯乙醇 在 Novozym 51003 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以64%的产率得到3-{[4-(2-hydroxyethyl)phenyl]amino}-1,4-dioxo-1,4-dihydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity

  摘要：

  Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a co-solvent, dimethylformamide, under mild reaction conditions in a vessel open to air at pH 4.5 and pH 6.0.Anticancer screening showed that the aminonaphthoquinones exhibited potent cytostatic effects particularly against the UACC62 (melanoma) cancer cell line (GI(50) = 3.98-7.54 mu M). One compound exhibited potent cytostatic effects against both the TK10 (renal) and the UACC62 (melanoma) cancer cell line. The cytostatic effects of this compound (GI(50) = 8.38 mu M) against the TK10 cell line was almost as good as that of the anticancer agent, etoposide (GI(50) = 7.19 mu M). Two compounds exhibited potent cytostatic effects against both the UACC62 (melanoma) and the MCF7 (breast) cancer cell lines. The total growth inhibition (TGI) of most of the compounds was better than that of etoposide against the UACC62 cell line. Three compounds (TGI = 7.17-7.94 mu M) exhibited potent cytostatic effects against the UACC62 cell line which was 7 to 8-fold better than that of etoposide (TGI = 52.71 mu M).The results are encouraging for further study of the aminonaphthoquinones for potential application in anticancer therapy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.028

文献信息

• A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity
  作者：Kevin W. Wellington、Natasha I. Kolesnikova

  DOI：10.1016/j.bmc.2012.05.028

  日期：2012.7

  Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a co-solvent, dimethylformamide, under mild reaction conditions in a vessel open to air at pH 4.5 and pH 6.0.Anticancer screening showed that the aminonaphthoquinones exhibited potent cytostatic effects particularly against the UACC62 (melanoma) cancer cell line (GI(50) = 3.98-7.54 mu M). One compound exhibited potent cytostatic effects against both the TK10 (renal) and the UACC62 (melanoma) cancer cell line. The cytostatic effects of this compound (GI(50) = 8.38 mu M) against the TK10 cell line was almost as good as that of the anticancer agent, etoposide (GI(50) = 7.19 mu M). Two compounds exhibited potent cytostatic effects against both the UACC62 (melanoma) and the MCF7 (breast) cancer cell lines. The total growth inhibition (TGI) of most of the compounds was better than that of etoposide against the UACC62 cell line. Three compounds (TGI = 7.17-7.94 mu M) exhibited potent cytostatic effects against the UACC62 cell line which was 7 to 8-fold better than that of etoposide (TGI = 52.71 mu M).The results are encouraging for further study of the aminonaphthoquinones for potential application in anticancer therapy. (C) 2012 Elsevier Ltd. All rights reserved.