1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione | 109899-85-6

• 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
• 英文名称: 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione
• 英文别名: 1-(2-Hydroxy-phenyl)-3-(3-nitro-phenyl)-propan-1,3-dion；1,3-Propanedione, 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-
• CAS: 109899-85-6
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: WDADIVYQICQOPD-UHFFFAOYSA-N

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-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione 在 tin 、 乙醇 、 氢溴酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 meta-aminoflavone
  参考文献：
  名称：

  Virkar, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1942, vol. 11/3 A, p. 136,138

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-(3-nitrobenzoyloxy)acetophenone 在 氢氧化钾 作用下， 生成 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)propane-1,3-dione
  参考文献：
  名称：

  取代的黄酮，4-硫代黄酮和4-亚氨基黄酮的合成和抗菌活性。

  摘要：

  黄酮，4-硫代黄酮和4-亚氨基黄酮的合成是通过取代相应化合物的A，B和AB环中的可变卤素，甲基，甲氧基和硝基进行的，我们在此也报告了它们的抗菌活性。发现大多数合成的化合物对大肠杆菌，枯草芽孢杆菌，弗氏志贺氏菌，金黄色沙门氏菌，伤寒沙门氏菌和铜绿假单胞菌具有活性。发现4-硫代黄酮和4-亚氨基黄酮的活性高于其相应的黄酮类似物的活性。在环B的4'-位具有取代基（如F，OMe和NO2）的被研究化合物显示出增强的活性，所研究化合物中负电基团的存在与抗菌活性直接相关。

  DOI：

  10.1016/j.bmc.2006.03.031

文献信息

• Pharmacophore and docking-based hierarchical virtual screening for the designing of aldose reductase inhibitors: synthesis and biological evaluation
  作者：Bhawna Vyas、Manjinder Singh、Maninder Kaur、Om Silakari、Malkeet Singh Bahia、Baldev Singh

  DOI：10.1007/s00044-016-1510-5

  日期：2016.4

  A set of 54 studied flavonoid inhibitors of aldose reductase (ALR2) enzyme has been utilized for pharmacophore modeling and 3D-QSAR analysis using “PHASE” program of Schrödinger software. The generated pharmacophore model (AADRR.1109) was challenged to screen “PHASE” database to identify new ALR2 inhibitors. The retrieved hits were employed for docking analysis and pharmacokinetic parameter calculation

  使用Schrödinger软件的“ PHASE”程序，已对54种已研究的醛糖还原酶（ALR2）类黄酮类抑制剂进行了药效团建模和3D-QSAR分析。挑战生成的药效团模型（AADRR.1109）以筛选“ PHASE”数据库，以鉴定新的ALR2抑制剂。将检索到的命中物用于对接分析和药代动力学参数计算以获得口服活性分子。为了预测最终检索到的命中的活动，开发了3D-QSAR模型，并根据各种统计参数选择了最佳模型（R 2列0.719；Q 2检验 0.647和SD 0.663）。总共合成了五个筛选的分子，这些分子显示出更好的预测活性，并评估了其在体外对ALR2的抑制活性。所有测试的分子均显示低于40 µM的ALR2抑制活性（IC 50）。另外，还确定了合成分子的自由基清除潜能，其在控制糖尿病并发症的进展中起着有用的作用。所有分子均显示出良好的抗氧化潜能，因此，将来可以探索设计的分子以改善糖尿病并发症的发生。
• Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones
  作者：Ehsan Ullah Mughal、Muhammad Ayaz、Zakir Hussain、Aurangzeb Hasan、Amina Sadiq、Muhammad Riaz、Abdul Malik、Samreen Hussain、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.03.031

  日期：2006.7.15

  Synthesis of flavones, 4-thioflavones and 4-iminoflavones was carried out with the substitution of variable halogens, methyl, methoxy and nitro groups in the A, B and AB rings of the respective compounds and we also report here their antibacterial activity. Most of the synthesized compounds were found to be active against Escherichia coli, Bacillus subtilis, Shigella flexnari, Salmonella aureus, Salmonella

  黄酮，4-硫代黄酮和4-亚氨基黄酮的合成是通过取代相应化合物的A，B和AB环中的可变卤素，甲基，甲氧基和硝基进行的，我们在此也报告了它们的抗菌活性。发现大多数合成的化合物对大肠杆菌，枯草芽孢杆菌，弗氏志贺氏菌，金黄色沙门氏菌，伤寒沙门氏菌和铜绿假单胞菌具有活性。发现4-硫代黄酮和4-亚氨基黄酮的活性高于其相应的黄酮类似物的活性。在环B的4'-位具有取代基（如F，OMe和NO2）的被研究化合物显示出增强的活性，所研究化合物中负电基团的存在与抗菌活性直接相关。
• Bowden, Keith; Chehel-Amiran, Mohsen, Journal of the Chemical Society. Perkin transactions II, 1986, p. 2039 - 2044
  作者：Bowden, Keith、Chehel-Amiran, Mohsen

  DOI：——

  日期：——
• Synthesis and Biochemical Evaluation of a Series of Aminoflavones as Potential Inhibitors of Protein-Tyrosine Kinases p56lck, EGFr, and p60v-src
  作者：Mark Cushman、Helen Zhu、Robert L. Geahlen、Alan J. Kraker

  DOI：10.1021/jm00046a020

  日期：1994.9

  A series of nitroflavones, 8a-p, and their corresponding aminoflavone hydrochloride salts, 10a-p, was synthesized. The preparation of nitroflavones 8b-i,o,p began with commercially available o-hydroxyacetophenones 2b-f which were converted to o-hydroxynitroacetophenones 3a-h via a variety of nitration methods, followed by condensation with nitrobenzoyl chlorides and cyclization under acidic condition. The nitroflavones 8aj-n were prepared by nitration of the corresponding flavones 7a-e. These new compounds were evaluated for their abilities to inhibit the in. vitro protein-tyrosine kinase activities of p56(1ck), EGFr, and p60(v-src), and all of the active compounds were amino-substituted flavones. None of the nitroflavones inhibited the enzymes. The most active substance in this series against p56(lck) was compound 10j, which had an IC50 of is mu M. When tested versus EGFr, compounds 10a,m displayed IC50's of 8.7 and 7.8 mu M, respectively. Against p60(v-src), 10a,m showed IC50 values of 28.8 and 38.4 mu M, respectively.
• Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1007/s00706-006-0550-9

  日期：2006.12

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.