(E)-2'-hydroxy-2-nitrochalcone | 73386-22-8

• 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: (E)-2'-hydroxy-2-nitrochalcone
• 英文别名: 2'-hydroxy-2-nitrochalcone；2'-hydroxy-2-nitro-trans-chalcone；2'-Hydroxy-2-nitro-trans-chalkon；1-(2-Hydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one；(E)-1-(2-hydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one
• CAS: 73386-22-8
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: FMSBHAKDHXMYSB-MDZDMXLPSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  476.6±45.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2'-hydroxy-2-nitrochalcone 在 双氧水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以84%的产率得到2-nitrocinnamic acid
  参考文献：
  名称：

  Solvent-Dependent Regioselective Oxidation oftrans-Chalcones using Aqueous Hydrogen Peroxide

  摘要：

  A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-beta-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields.

  DOI：

  10.5935/0103-5053.20130063
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 邻硝基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以76%的产率得到(E)-2'-hydroxy-2-nitrochalcone
  参考文献：
  名称：

  CBr4催化活化α,β-不饱和酮

  摘要：

  我们在这里表明，弱相互作用，如卤素键 (XB) 可用于激活 α,β-不饱和酮的羰基。四溴化碳 (CBr 4 ) 已被用作在无金属和无添加剂条件下从相应的 2'-羟基和 2'-氨基查耳酮选择性合成黄烷酮和氮杂黄烷酮的唯一试剂。DFT 计算支持 XB 在这些反应中查耳酮的氧和 CBr 4之间的催化作用。

  DOI：

  10.1039/d2ob01223e

文献信息

• Differences in antioxidant potential of chalcones in human serum: In vitro study
  作者：Tamara Janković、Nemanja Turković、Jelena Kotur-Stevuljević、Zorica Vujić、Branka Ivković

  DOI：10.1016/j.cbi.2020.109084

  日期：2020.6

  values. Samples with Ch11 and Ch13 showed significant negative correlation between TAS and TOS (p < 0.05 for both), but in Ch14 sample the negative correlation existed between TAS and PAB (p < 0.05). CONCLUSION Lower value of OS (i.e. better antioxidative potency) was noticed in samples with Ch11-Ch15. Electron-donor effects of substituent groups as a structural part of these chalcones could explain

  引言氧化剂和抗氧化剂之间的不平衡以氧化剂为先导，可能导致损害，被称为氧化应激。酶性或非酶性抗氧化剂（AO）均可减少促氧化剂如DNA，蛋白质和脂质损伤的多种作用。Chalcones（1,3-diaryl-2-propen-1-ones）是在植物中广泛生物合成的开链类黄酮。这项研究的目的是在体外模型中（天然条件下）测试15个查耳酮（Chs）的抗氧化能力，以及外源性氧化应激。材料与方法用0.25 mmol / L叔丁基氢过氧化氢（TBH）在健康个体的血清样品中诱导氧化应激，然后我们监测了各种浓度的查耳酮对氧化应激参数的影响：总抗氧化状态（TAS），总氧化状态（TOS），巯基总浓度（SHG）和氧化前-抗氧化平衡（PAB），以及计算出的氧化前评分，抗氧化评分和氧化评分（OS）。采用非参数重复测量方差分析（Friedman's test），以天然状态和TBH影响比较具有15种不同查耳酮的样品的抗氧化能
• One-pot synthesis of 2-(2-hydroxyaryl)quinolines: reductive coupling reactions of 2′-hydroxy-2-nitrochalcones
  作者：Ana I.R.N.A Barros、Artur M.S Silva

  DOI：10.1016/s0040-4039(03)01374-1

  日期：2003.7

  A one-pot synthesis of novel 2-(2-hydroxyaryl)quinolines have been developed from the intramolecular reductive coupling reactions of 2′-hydroxy-2-nitrochalcones, induced by stannous chloride in acidic medium (HCl/AcOH). In some cases these transformations can be performed with ammonium formate/Pd–C in methanol.

  通过在酸性介质（HCl / AcOH）中由氯化亚锡诱导的2'-羟基-2-硝基查耳酮的分子内还原偶联反应，已经开发出了一锅合成新型2-（2-羟基芳基）喹啉的方法。在某些情况下，可以用甲酸铵/钯-碳在甲醇中进行这些转化。
• Identification of bicyclic compounds that act as dual inhibitors of Bcl-2 and Mcl-1
  作者：Abhay Uthale、Aarti Anantram、Prasad Sulkshane、Mariam Degani、Tanuja Teni

  DOI：10.1007/s11030-022-10494-6

  日期：——

  Elevated expression of anti-apoptotic proteins, such as Bcl-2 and Mcl-1 contributes to poor prognosis and resistance to current treatment modalities in multiple cancers. Here, we report the design, synthesis and characterization of benzimidazole chalcone and flavonoid scaffold-derived bicyclic compounds targeting both Bcl-2 and Mcl-1 by optimizing the structural differences in the binding sites of both these proteins. Initial docking screen of Bcl-2 and Mcl-1 with pro-apoptotic protein Bim revealed possible hits with optimal binding energies. All the optimized bicyclic compounds were screened for their in vitro cytotoxic activity against two oral cancer cell lines (AW8507 and AW13516) which express high levels of Bcl-2 and Mcl-1. Compound 4d from the benzimidazole chalcone series and compound 6d from the flavonoid series exhibited significant cytotoxic activity (IC50 7.12 μM and 17.18 μM, respectively) against AW13516 cell line. Time Resolved-Fluorescence Resonance Energy Transfer (TR-FRET) analysis further demonstrated that compound 4d and compound 6d could effectively inhibit the Bcl-2 and Mcl-1 proteins by displacing their BH3 binding partners. Both compounds exhibited potent activation of canonical pathway of apoptosis evident from appearance of cleaved Caspase-3 and PARP. Further, treatment of oral cancer cells with the inhibitors induced dissociation of the BH3 only protein Bim from Mcl-1 and Bak from Bcl-2 but failed to release Bax from Bcl-xL thereby confirming the nature of compounds as BH3-mimetics selectively targeting Bcl-2 and Mcl-1. Our study thus identifies bicyclic compounds as promising candidates for anti-apoptotic Bcl-2/Mcl-1 dual inhibitors with a potential for further development.

  抗凋亡蛋白（如Bcl-2和Mcl-1）的表达升高会导致多种癌症预后不良，并导致对现有治疗方式的耐药性。在此，我们报告了苯并咪唑查尔酮和黄酮类化合物骨架衍生物双环化合物的设计、合成和表征，这些化合物通过优化Bcl-2和Mcl-1结合位点的结构差异，同时靶向这两种蛋白。通过将Bcl-2和Mcl-1与促凋亡蛋白Bim进行初步对接筛选，我们发现了具有最佳结合能的可能的靶向化合物。对所有优化后的双环化合物进行了体外细胞毒性活性筛选，以检测其对两种表达高水平Bcl-2和Mcl-1的口腔癌细胞系（AW8507和AW13516）的细胞毒性活性。苯并咪唑查尔酮系列中的化合物4d和黄酮类化合物系列中的化合物6d对AW13516细胞系表现出显著的细胞毒性活性（IC50分别为7.12 μM和17.18 μM）。时间分辨荧光共振能量转移（TR-FRET）分析进一步表明，化合物4d和化合物6d可通过置换其BH3结合伴侣来有效抑制Bcl-2和Mcl-1蛋白。从裂解的Caspase-3
• Reichel; Hempel, Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 184,193
  作者：Reichel、Hempel

  DOI：——

  日期：——
• Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships
  作者：Mauricio Cabrera、Macarena Simoens、Gabriela Falchi、M. Laura Lavaggi、Oscar E. Piro、Eduardo E. Castellano、Anabel Vidal、Amaia Azqueta、Antonio Monge、Adela López de Ceráin、Gabriel Sagrera、Gustavo Seoane、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2007.03.031

  日期：2007.5

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.