1-(2-羟基苯基)-3-(2-硝基苯基)丙烷-1,3-二酮 | 84634-63-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-(2-羟基苯基)-3-(2-硝基苯基)丙烷-1,3-二酮
• 英文名称: 1-(2-hydroxy-phenyl)-3-(2-nitro-phenyl)-propane-1,3-dione
• 英文别名: 1-(2-Hydroxy-phenyl)-3-(2-nitro-phenyl)-propan-1,3-dion；1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(2-nitrophenyl)-；1-(2-hydroxyphenyl)-3-(2-nitrophenyl)propane-1,3-dione
• CAS: 84634-63-9
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: ZWIBBTPQRAMQCW-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C
• 沸点：
  501.9±35.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-羟基苯基)-3-(2-硝基苯基)丙烷-1,3-二酮 在 tetraphosphorus decasulfide 、 硫酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Hasan, Aurangzeb; Mughal; Sadiq, Asian Journal of Chemistry, 2012, vol. 24, # 10, p. 4361 - 4364

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-(2-nitrobenzoyloxy)acetophenone 在 氢氧化钾 作用下， 以 吡啶 为溶剂， 生成 1-(2-羟基苯基)-3-(2-硝基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0

文献信息

• Cyclic amidines. Part XXIII. Dibenzo[b,h][1]benzopyrano[2,3,4-de][1,6]naphthyridines and their molecular orientation in carcinogenesis
  作者：D. G. Bloomfield、M. W. Partridge、H. J. Vipond

  DOI：10.1039/j39700002647

  日期：——

  derivatives, are described. An explanation is given of the differences in carcinogenic activity of the 2-, 7-, and 12-methyl derivatives, consistent with specific molecular orientations for carcinogenesis similar to those deduced for tricycloquinazoline and its derivatives.

  取代的二苯并[ b，h ] [1,6]萘啶和取代的[1]苯并吡喃并[3,2 - c ]喹啉-7-环的环化，以及N-羧基邻氨基苯甲酸酐与取代的1,3-的缩合描述了二苯基丙烷-1,3-二酮，然后进行还原环化，明确导致二苯并[ b，h ] [1]苯并吡喃并[2,3,4- de ] [1,6]萘啶和五个异构甲基衍生物。给出了2-，7-和12-甲基衍生物的致癌活性差异的解释，这与致癌作用的特定分子方向一致，类似于对三环喹唑啉及其衍生物的推导。
• Synthesis and Anti-cancer Activities of Apigenin Derivatives
  作者：Xing Zheng、Liuying Yu、Jing Yang、Xu Yao、Wenna Yan、Shaowei Bo、Ya Liu、Yun Wei、Zhiyi Wu、Guan Wang

  DOI：10.2174/1573406410666140307152557

  日期：2014.3.7

  A novel series of apigenin derivatives with phloroglucinol or resorcinol as raw materials were synthesized according to Baker-Venaktaraman reaction and their in vitro inhibitory activities on colorectal adenocarcinoma (HT-29) and leucocythemia (HL-60) cell lines were evaluated by the standard methyl thiazole tetrazolium (MTT) method. The results of biological test showed that some of apigenin derivatives possessed stronger anti-cancer activities than apigenin. Compound 6 showed the strongest activity against colorectal adenocarcinoma (HT-29) and leucocythemia (HL-60) cell lines with IC50 valure of 2.03±0.22 µM, 2.25±0.42 µM, it was better than 5-FU (12.92±0.61 µM, 9.56±0.16 µM), which shows a potential compound for colorectal adenocarcinoma and leucocythemia.

  根据贝克-维纳克塔拉曼反应合成了一系列新型芹菜素衍生物，并以氯代葡萄糖苷醇或间苯二酚为原料，采用标准甲基噻唑四氮唑（MTT）法评价了它们对结直肠腺癌（HT-29）和白血病（HL-60）细胞株的体外抑制活性。生物测试结果表明，一些芹菜素衍生物比芹菜素具有更强的抗癌活性。化合物 6 对结直肠腺癌（HT-29）和白血病（HL-60）细胞株的活性最强，其 IC50 值分别为 2.03±0.22 µM、2.25±0.42 µM，优于 5-FU（12.92±0.61 µM、9.56±0.16 µM），这表明该化合物具有治疗结直肠腺癌和白血病的潜力。
• Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
  作者：Mariel Marde、Juan Zinczuk、María I. Colombo、Cristina Wasowski、Haydee Viola、Claudia Wolfman、Jorge H. Medina、Edmundo A. Rúveda、Alejandro C. Paladini

  DOI：10.1016/s0960-894x(97)00343-0

  日期：1997.8

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.
• Doyle et al., Scientific Proceedings of the Royal Dublin Society, 1948, vol. 24, p. 291,299
  作者：Doyle et al.

  DOI：——

  日期：——
• Srivastava; Satsangi; Kishore, Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 12, p. 1512 - 1514
  作者：Srivastava、Satsangi、Kishore

  DOI：——

  日期：——