4-(2-nitrobenzylideneamino)naphthalene-1,2-dione | 1386994-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-nitrobenzylideneamino)naphthalene-1,2-dione
• 英文别名: 4-[(2-Nitrophenyl)methylideneamino]naphthalene-1,2-dione；4-[(2-nitrophenyl)methylideneamino]naphthalene-1,2-dione
• CAS: 1386994-22-4
• 化学式: C₁₇H₁₀N₂O₄
• 分子量: 306.277
• InChiKey: LNUURTYYRPBCAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-nitrobenzylideneamino)naphthalene-1,2-dione 、 氨基硫脲单盐酸盐 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, cytotoxic evaluation, docking and in silico pharmacokinetic prediction of 4-arylideneamino/cycloalkylidineamino 1, 2-naphthoquinone thiosemicarbazones

  摘要：

  In an attempt to develop potent anticancer agents, a series of 4-arylideneamino/cycloalkylidineamino-1, 2-naphthoquinone thiosemicarbazones were synthesized and characterized using FT-IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. The compounds were screened for antiproliferative activity against three human cancer cell lines (Hep-G2, MG-63 and MCF-7) using the MTT assay. Significant anticancer activity was observed for several members of the series. The compounds 4-(3, 4, 5-trimethoxybenzylidene amino) 1, 2-naphthoquinone-2-thiosemicarbazone (TS10) and 4-(4-hydroxy-3-methoxy benzylideneamino) 1, 2-naphthoquinone-2-thiosemicarbazone (TS13) were active cytotoxic agents in all three cancer cell lines, with IC50 values in the range of 3.5-6.4 mu M. Further evaluation of some of these potent cytotoxic compounds demonstrated their good safety profile in a normal cell line (MCF-12A). Docking experiments showed a good correlation between the predicted glide scores and the IC50 values of these compounds. In silico ADME studies revealed that these compounds can be used for second generation development.

  DOI：

  10.3109/14756366.2012.721783
• 作为产物：
  描述：

  orange II 在 盐酸 、 iron(III) chloride 、 sodium azide 、 sodium dithionite 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 4-(2-nitrobenzylideneamino)naphthalene-1,2-dione
  参考文献：
  名称：

  Synthesis, characterization, in vitro anticancer activity, and docking of Schiff bases of 4-amino-1,2-naphthoquinone

  摘要：

  A series of Schiff bases of 4-amino-1,2-naphthoquinone were synthesized, purified, characterized, and evaluated for cytotoxicity against a panel of human cancer cell lines (Hep-G(2), MG-63, and MCF-7). The cells were dosed with these Schiff bases at varying concentrations, and cell viability was measured by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Significant anticancer activities were observed in vitro for some members of the series and compounds 4-(3,4,5-trimethoxybenzylideneamino)naphthalene-1,2-dione (S10) as well as 4-(4-hydroxy-3-methoxybenzylideneamino)naphthalene-1,2-dione (S13) are active cytotoxic agents against different cancer cell lines with IC50 values in the range of 5.91-9.98 mu M. The structures of synthesized compounds were established by spectroscopic (FT-IR, H-1 NMR, C-13 NMR) and elemental analysis. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of Topoisomerase-II (TP-II) by using Schrodinger molecular modeling software package. Docking experiments showed a good correlation between their predicted glide scores and the observed IC50 values of synthesized compounds. Structure-activity relationships indicated that presence of electron donating groups on phenyl ring of Schiff bases enhances the activity but Schiff base with electron withdrawing substituents on phenyl ring shows diminished activity.

  DOI：

  10.1007/s00044-012-0150-7

文献信息

• Synthesis, characterization, in vitro anticancer activity, and docking of Schiff bases of 4-amino-1,2-naphthoquinone
  作者：S. Shukla、R. S. Srivastava、S. K. Shrivastava、A. Sodhi、Pankaj Kumar

  DOI：10.1007/s00044-012-0150-7

  日期：2013.4

  A series of Schiff bases of 4-amino-1,2-naphthoquinone were synthesized, purified, characterized, and evaluated for cytotoxicity against a panel of human cancer cell lines (Hep-G(2), MG-63, and MCF-7). The cells were dosed with these Schiff bases at varying concentrations, and cell viability was measured by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Significant anticancer activities were observed in vitro for some members of the series and compounds 4-(3,4,5-trimethoxybenzylideneamino)naphthalene-1,2-dione (S10) as well as 4-(4-hydroxy-3-methoxybenzylideneamino)naphthalene-1,2-dione (S13) are active cytotoxic agents against different cancer cell lines with IC50 values in the range of 5.91-9.98 mu M. The structures of synthesized compounds were established by spectroscopic (FT-IR, H-1 NMR, C-13 NMR) and elemental analysis. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of Topoisomerase-II (TP-II) by using Schrodinger molecular modeling software package. Docking experiments showed a good correlation between their predicted glide scores and the observed IC50 values of synthesized compounds. Structure-activity relationships indicated that presence of electron donating groups on phenyl ring of Schiff bases enhances the activity but Schiff base with electron withdrawing substituents on phenyl ring shows diminished activity.
• Synthesis, cytotoxic evaluation, docking and <i>in silico</i> pharmacokinetic prediction of 4-arylideneamino/cycloalkylidineamino 1, 2-naphthoquinone thiosemicarbazones
  作者：Shubhanjali Shukla、Radhey Shyam Srivastava、Sushant Kumar Shrivastava、Ajit Sodhi、Pankaj Kumar

  DOI：10.3109/14756366.2012.721783

  日期：2013.12.1

  In an attempt to develop potent anticancer agents, a series of 4-arylideneamino/cycloalkylidineamino-1, 2-naphthoquinone thiosemicarbazones were synthesized and characterized using FT-IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. The compounds were screened for antiproliferative activity against three human cancer cell lines (Hep-G2, MG-63 and MCF-7) using the MTT assay. Significant anticancer activity was observed for several members of the series. The compounds 4-(3, 4, 5-trimethoxybenzylidene amino) 1, 2-naphthoquinone-2-thiosemicarbazone (TS10) and 4-(4-hydroxy-3-methoxy benzylideneamino) 1, 2-naphthoquinone-2-thiosemicarbazone (TS13) were active cytotoxic agents in all three cancer cell lines, with IC50 values in the range of 3.5-6.4 mu M. Further evaluation of some of these potent cytotoxic compounds demonstrated their good safety profile in a normal cell line (MCF-12A). Docking experiments showed a good correlation between the predicted glide scores and the IC50 values of these compounds. In silico ADME studies revealed that these compounds can be used for second generation development.