(5Z)-5-(3-nitrobenzylidene)imidazolidine-2,4-dione | 136949-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5Z)-5-(3-nitrobenzylidene)imidazolidine-2,4-dione
• 英文别名: (5Z)-5-[(3-nitrophenyl)methylidene]imidazolidine-2,4-dione
• CAS: 136949-31-0
• 化学式: C₁₀H₇N₃O₄
• 分子量: 233.183
• InChiKey: UXLLZDWZJYMJKG-YVMONPNESA-N

物化性质

• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z)-5-(3-nitrobenzylidene)imidazolidine-2,4-dione 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.33h， 以45%的产率得到5-(3-nitrobenzylidene)-3-(4-methylphenylsulfonyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction

  摘要：

  Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)-diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly, beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199 62%) for (M14) Melanoma cells was observed at the tested concentration (10 mu M) ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.

  DOI：

  10.1016/j.ejmech.2010.02.038
• 作为产物：
  描述：

  2-Amino-5-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one 在 sodium hydroxide 作用下， 反应 0.05h， 以83%的产率得到(5Z)-5-(3-nitrobenzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Mukerjee, Arya K.; Joseph, Kiran; Homami, Seyed-Saied, Heterocycles, 1991, vol. 32, # 7, p. 1317 - 1325

  摘要：

  DOI：

文献信息

• Anticonvulsant Activity of Phenylmethylenehydantoins:  A Structure−Activity Relationship Study
  作者：Jeyanthi Chinnappa Thenmozhiyal、Peter Tsun-Hon Wong、Wai-Keung Chui

  DOI：10.1021/jm030450c

  日期：2004.3.1

  Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and the selection of substituents was guided by Craig's plot. Phenylmethylenehydantoins substituted with alkyl (2, 3, 5, 6, 12, 14), halogeno (35, 38, 41), trifluoromethyl (11), and alkoxyl (23) groups at the phenyl ring were found to exhibit good anticonvulsant activity with EDMES(2.5) ranging from 28 to 90 mg/kg. Substitution of polar groups such as -NO2, -CN, and -OH was found to be less active or inactive on PMHs. Replacement of the phenyl ring with heteroaromatic rings reduced or caused the loss of anticonvulsant activity. The study identified two PMHs, 14 (EDMES(2.5) = 28 +/- 2 mg/kg) and 12 (EDMES(2.5) = 39 4 mg/kg), to be the most active candidates of the series, which are comparable to phenytoin (55, EDMES(2.5) = 30 +/- 2 mg/kg) in their protection against seizure. Multivariate analysis performed on the whole series of 54 PMHs further supported the finding that the alkylated phenylmethylenehydantoins are the best acting compounds. The SAR model derived on the basis of 12 of the most active phenylmethylenehydantoins demonstrated good predicting ability (root-mean-square error of prediction (RMSEP) = 0.134; RMSEE = 0.057) and identified LUMO energy and the log P as critical parameters for their anticonvulsant activity.
• Mukerjee, Arya K.; Joseph, Kiran; Homami, Seyed-Saied, Heterocycles, 1991, vol. 32, # 7, p. 1317 - 1325
  作者：Mukerjee, Arya K.、Joseph, Kiran、Homami, Seyed-Saied、Tikdari, Ahmad M.

  DOI：——

  日期：——
• Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction
  作者：Ibrahim M. El-Deeb、Said M. Bayoumi、Magda A. El-Sherbeny、Alaa A.-M. Abdel-Aziz

  DOI：10.1016/j.ejmech.2010.02.038

  日期：2010.6

  Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)-diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly, beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199 62%) for (M14) Melanoma cells was observed at the tested concentration (10 mu M) ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.