7-羟基-2-(4'-硝基苯基)色酮 | 131944-42-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 7-羟基-2-(4'-硝基苯基)色酮
• 中文别名: 4H-1-苯并吡喃-4-酮,7-羟基-2-(4-硝基苯基)-
• 英文名称: 7-hydroxy-4'-nitroflavone
• 英文别名: 7-Hydroxy-2-(4-nitrophenyl)chromen-4-one
• CAS: 131944-42-8
• 化学式: C₁₅H₉NO₅
• 分子量: 283.24
• InChiKey: OPUYQGBDVLHIPY-UHFFFAOYSA-N

物化性质

• 熔点：
  298-299 °C
• 沸点：
  530.8±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-羟基-2-(4'-硝基苯基)色酮 在 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 2-(4-aminophenyl)-7-(3-bromopropoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Multifunctional tacrine–flavonoid hybrids with cholinergic, β-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease

  摘要：

  A new series of tacrine flavonoid hybrids (13a u) had been designed, synthesized, and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). In vitro studies showed that most of the molecules exhibited a significant ability to inhibit ChE and self-induced amyloid-beta (A beta(1-42)) aggregation. Kinetic and molecular modeling studies also indicated compounds were mixed-type inhibitors, binding simultaneously to active, peripheral and mid-gorge sites of AChE. Particularly, compound 13k was found to be highly potent and showed a balanced inhibitory profile against ChE and self-induced A beta(1-42) aggregation. Moreover, it also showed excellent metal chelating property and low cell toxicity. These results suggested that 13k might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.024
• 作为产物：
  描述：

  丹皮酚 在 四氯化碳 、 吡啶盐酸盐 、 magnesium 、 lithium hexamethyldisilazane 作用下， 以 喹啉 为溶剂， 反应 29.0h， 生成 7-羟基-2-(4'-硝基苯基)色酮
  参考文献：
  名称：

  类黄酮类似物的合成及其蛋白酪氨酸激酶抑制活性。

  摘要：

  用过量的双（三甲基甲硅烷基）酰胺锂，然后用碳酸二烷基酯处理邻羟基苯乙酮2a-e，得到3-（2-羟基芳基）-3-氧代丙酸烷基酯3a-e。后者的物质通过其镁螯合物与苯甲酰氯的反应转化为一系列的3-（烷氧基羰基）-2-芳基黄酮，随后将其精加工成各种类黄酮。测试了这些化合物抑制p56lck体外蛋白酪氨酸激酶活性的能力，该酶被认为在淋巴细胞活化过程中在介导CD4受体的信号转导中起关键作用。所有的活性化合物在2-芳基环的4'-位具有氨基或羟基取代基。本研究中制备的活性最高的物质是化合物17c，其功效比天然产物槲皮素（1）高约1个数量级。化合物17c相对于ATP是p56lck的竞争性抑制剂，并且相对于蛋白质丝氨酸/苏氨酸激酶，对蛋白质酪氨酸的抑制具有高度选择性。

  DOI：

  10.1021/jm00106a047

文献信息

• Synthesis and biological evaluation of novel flavone/triazole/benzimidazole hybrids and flavone/isoxazole-annulated heterocycles as antiproliferative and antimycobacterial agents
  作者：Yerrabelly Jayaprakash Rao、Thummala Sowjanya、Gogula Thirupathi、Nandula Yadagiri Sreenivasa Murthy、Sudha Sravanti Kotapalli

  DOI：10.1007/s11030-018-9833-4

  日期：2018.11

  AbstractA series of new flavone/isoxazole fused heterocycles 5a–f and flavone/1,2,3-triazole/benzimidazole hybrid heterocycles compounds 7a–t were synthesized via an intramolecular cyclization and Cu(I)-catalyzed click 1,3-dipolar cycloaddition. The products were evaluated for their antiproliferative activity against human breast cancer cell line (MCF-7) using sulforhodamine B assay (SRB) and antimycobacterial

  摘要通过分子内环化和Cu（I）催化的点击1,3-偶极环加成反应合成了一系列新的黄酮/异恶唑稠合杂环5a-f和黄酮/ 1,2,3-三唑/苯并咪唑杂合杂环化合物7a-t。使用磺基罗丹明B测定（SRB）评估了产品对人乳腺癌细胞系（MCF-7）的抗增殖活性，并使用浊度测定法评估了产品的抗分枝杆菌活性。大多数测试化合物显示出抗增殖活性和抗分枝杆菌活性。化合物7l，7q和7r显示出中等的抗增殖活性，IC50值为 17.9、14.2、19.1（\ upmu \ hbox M} \）分别地，化合物5a和化合物5a在30 （\ upmu \ hbox M} \）浓度下显示出中等的抗分枝杆菌活性，抑制率为41.7％  。 图形概要
• Synthesis and Antiproliferative Activity of Some Dihydro-1H-furo[2,3-c]pyrazole-Flavone Hybrids
  作者：Venkata Swamy Tangeti、D. Vasundhara、K.V.V.V. Satyanarayana、Kaja Srinivas Pavan Kumar

  DOI：10.14233/ajchem.2017.20550

  日期：——

  A new series of dihydro-1H-furo[2,3-c]pyrazole-flavone hybrids were synthesized from one-pot four-component reaction of b-keto ester (1), hydrazine (2), 7-hydroxy 8-formyl flavones (3), pyridiniumylide (4) in presence of NEt3 as catalyst under ethanol reflux conditions and their antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, furo[2,3-c]pyrazole-flavone with C4-methoxy substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, (4S,5S)-ethyl 4-(7-hydroxy-5-methoxy-4-oxo-2-(2,4,6-trimethoxyphenyl)-4H-chromen-8-yl)-3-methyl-4,5-dihydro-1H-furo[2,3-c]pyrazole-5-carboxylate (8r) showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the dihydro-1H-furo[2,3-c]pyrazole-flavones are specifically target the cancer cell lines.

  一系列二氢-1H-呋喃[2,3-c]吡唑-黄酮杂合物通过一锅四组分反应合成，反应物包括β-酮酯（1）、肼（2）、7-羟基-8-醛黄酮（3）和吡啶亚胺（4），在三乙胺（NEt3）催化下于乙醇回流条件下进行。随后评估了这些化合物对人类癌细胞系的抗增殖活性，包括喉癌（Hep2）、肺腺癌（A549）和宫颈癌（HeLa）。在这些化合物中，C4-取代的甲氧基二氢-1H-呋喃[2,3-c]吡唑-黄酮被选为进一步结构-活性关系（SAR）研究的对象。在这些衍生物中，(4S,5S)-乙基4-(7-羟基-5-甲氧基-4-氧基-2-(2,4,6-三甲氧基苯基)-4H-香豆烯-8-基)-3-甲基-4,5-二氢-1H-呋喃[2,3-c]吡唑-5-羧酸酯（8r）对所有三种癌细胞系表现出最强的细胞毒活性。毒性研究表明，二氢-1H-呋喃[2,3-c]吡唑-黄酮特别靶向癌细胞系。
• A method for the facile synthesis of ring-A hydroxylated flavones
  作者：Mark Cushman、Dhanapalan Nagarathnam

  DOI：10.1016/s0040-4039(00)97100-4

  日期：1990.1

  A general method for the facile synthesis of ring-A hydroxylated flavones is described. Treatment of the hydroxylated acetophenones 6a–d with enough lithium bis(trimethyl)silyl amide to deprotonate all of the phenols as well as to generate the lithium enolate of the ketone, followed by addition of the acid chlorides 7a–d, gave the 1,3-diketones 8a–g, which were cyclized to the desired products 9a–g

  描述了容易合成环A-羟基黄酮的一般方法。用足够的双（三甲基）甲硅烷基氨基锂处理羟基苯乙酮6a-d，以使所有酚去质子化，并生成酮的烯醇锂，然后添加酰氯7a-d，得到1， 3-二酮8a-g，高产率地环化成所需的产物9a-g。
• Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor
  作者：Jiraporn Ungwitayatorn、Chanpen Wiwat、Weerasak Samee、Patcharawee Nunthanavanit、Narumol Phosrithong

  DOI：10.1016/j.molstruc.2011.06.035

  日期：2011.8

  Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3'-trifluoromethyl phenyl)-3-(3 ''-trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 mu M. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series. (C) 2011 Elsevier B.V. All rights reserved.
• A rational approach to the design of flavones as xanthine oxidase inhibitors
  作者：L Costantino、G Rastelli、A Albasini

  DOI：10.1016/0223-5234(96)85878-8

  日期：1996.1

  In the light of previous QSAR studies on flavones as inhibitors of xanthine oxidase, we synthesized and tested a new series of 7-hydroxyflavones carrying a wide and balanced variety of substituents (pi, sigma(p)) at the 4' position in order to explore the effect of substituents at this position on the xanthine oxidase inhibitory activity. The results of pK(a) determinations show that the electronic effects of the substituents are not transferred to the hydroxyl at C7, previously found to be fundamental for activity. An excellent correlation is found between molar refractivity of the substituents and the inhibitory activity. These results, applied to the more active 5,7-dihydroxyflavones, allowed the design and synthesis of a very active inhibitor, with an IC50 in the nanomolar range. On interpretative grounds, C4' substituents of flavones are involved in dispersion interactions with the enzyme. The calculation of quantum chemical polarizabilities and solvent accessible surface areas suggests the existence of pi-pi stacking interactions with an aromatic aminoacidic residue of the enzyme.