1-<2-Hydroxy-phenyl>-3--propen-(2)-on-(1) | 36715-65-8

• 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: 1-<2-Hydroxy-phenyl>-3--propen-(2)-on-(1)
• 英文别名: 1-(2-hydroxyphenyl)-3-(9-anthracyl)propenone；1-(2-hydroxyphenyl)-3-anthracen-9-ylprop-2-en-1-one；3-Anthracen-9-yl-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 36715-65-8
• 化学式: C₂₃H₁₆O₂
• 分子量: 324.379
• InChiKey: IQBCAXKWFWUTKA-UHFFFAOYSA-N

物化性质

• 熔点：
  130.8 °C(Solv: methanol (67-56-1))
• 沸点：
  569.1±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<2-Hydroxy-phenyl>-3--propen-(2)-on-(1) 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(anthracen-9-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 2-aryl-4H-chromen-4-one Derivatives Against Chikungunya Virus

  摘要：

  合成并评价了一系列十九种2-芳基-4H-色烯-4-酮衍生物2a-2s对Vero细胞培养中基孔肯雅病毒（LR2006_OPY1）的抗病毒活性，通过CPE减少试验。发现三种化合物2a、2b和2g在浓度（IC50）分别为0.44 M、0.45 M和2.02 M时具有活性。在色烯酮的2位具有杂环环的化合物2a和2b被发现是ChikV的强效抑制剂。通过Vero细胞培养进行了细胞毒性研究，化合物2a和2b显示出SI为100。进行了分子对接模拟以理解可能的作用机制。

  DOI：

  10.2174/1570180813666160711163349
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 9-蒽甲醛 在 barium hydroxide octahydrate 作用下， 以 乙醇 为溶剂， 以78%的产率得到1-<2-Hydroxy-phenyl>-3--propen-(2)-on-(1)
  参考文献：
  名称：

  2'-羟基查尔酮可逆环化为黄烷酮的不对称离子对催化：平衡反应的不对称催化

  摘要：

  简单的 2'-羟基查尔酮 (1) 到黄烷酮 (2) 的不对称催化环化是查尔酮异构酶反应的模型，已被实现为手性季铵盐（例如，9-蒽基甲基辛可宁鎓）的催化不对称离子配对过程氯化物；9-Am-CN-Cl) 和 NaH 作为小分子助催化剂。在甲苯/CHCl3 溶液中，该过程达到了高达 S = 14.4 (er = 93.5:6.5) 的固有对映选择性。可逆反应分两步进行：快速初始反应接近 KR/S = 4.5 的准平衡，然后是接近 Krac = 9 的第二个缓慢外消旋阶段。提出了可逆性。氘从共溶剂 CDCl3 转移到产物 2 以及由 2 和 1 形成的迈克尔共轭物的分离证明了黄烷酮烯醇化物离子对的中介作用。动力学模型显示出与实验观察到的物种浓度和对映体过量 2 的独特的时间依赖性演化非常一致。该反应是查尔酮异构酶酶促反应的化学模型。此外，它是研究接近平衡的可逆不对称催化剂的特征行为的理想模型。该反

  DOI：

  10.1002/ejoc.201200838

文献信息

• Synthesis and characterization of some substituted chromones as an anti-infective and antioxidant agents
  作者：Milind Rode、R. C. Gupta、B. K. Karale、S. S. Rindhe

  DOI：10.1002/jhet.5570450607

  日期：2008.11

  A series of substituted chromones were synthesized and characterized by spectral data. Some of the synthesized compounds were tested for in-vitro antibacterial, antifungal and antioxidant activity. Two compounds have shown very good antioxidant activity and some of the chromone derivatives have exhibited moderate antibacterial and antifungal activity.

  合成了一系列取代的色酮，并通过光谱数据对其进行了表征。测试了一些合成的化合物的体外抗菌，抗真菌和抗氧化活性。两种化合物显示出非常好的抗氧化活性，某些色酮衍生物显示出中等的抗菌和抗真菌活性。
• A new pyrazoline-based probe of quenched fluorescent reversible recognition for Cu 2+ and its application in cells
  作者：Ying-Peng Zhang、Yu-Ying Dong、Yun-Shang Yang、Hui-Chen Guo、Bi-xia Cao、Shi-Qi Sun

  DOI：10.1016/j.saa.2017.01.042

  日期：2017.4

  recognition properties of this compound was investigated by UV–vis absorption and fluorescence spectrophotometry. The results showed that the probe D forms a 1:1 complex with Cu2 + and displayed a linear fluorescence response to Cu2 + with a detection limit of 1.94 × 10− 7 M. In addition, the probe have a good biocompatibility in living cells.

  设计并合成了一种新型的基于吡唑啉的探针D，该探针可以用作高灵敏度，选择性和可逆识别荧光的探针，用于检测Cu 2 +。通过紫外可见吸收和荧光分光光度法研究了该化合物的识别特性。结果表明，该探针d形成1：1的复合物与铜2 +和显示一个线性荧光响应的Cu 2 +与1.94×10的检测极限- 7  M.另外，探针在活良好的生物相容性细胞。
• Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling
  作者：Bubul Das、Nikita Chakraborty、Hirendra Nath Dhara、Pratip Bhattacharyya、Bhisma K. Patel

  DOI：10.1021/acs.joc.3c02479

  日期：2024.1.19

  A mild and concise method for the synthesis of chromenopyrrole from 2′-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on the C═C bond of 2′-hydroxychalcone and 1,3-dipolarophile, generated in situ by the reaction of ethyl isocyanoacetate and AgOAc. This is then followed by an intramolecular C–O bond formation with the −OH group and C5–H of the in situ generated

  设计了一种温和、简洁的从 2'-羟基查尔酮合成色吡咯的方法。该反应通过 2'-羟基查耳酮和 1,3-亲偶极试剂的 C=C 键上的初始 [3 + 2] 环加成进行，该键是由异氰基乙酸乙酯和 AgOAc 反应原位生成的。然后与原位生成的吡咯的 -OH 基团和 C5-H 形成分子内 C-O 键，形成色并吡咯。
• Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
  作者：Vishnu Nayak Badavath、S. Ciftci-Yabanoglu、Soumendranath Bhakat、Ajay Kumar Timiri、Barij N. Sinha、G. Ucar、Mahmoud E.S. Soliman、Venkatesan Jayaprakash

  DOI：10.1016/j.bioorg.2014.11.008

  日期：2015.2

  A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with K-i value for MAO-B of 0.16 +/- 0.01 mu M comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 +/- 0.01 mu M). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO. (C) 2014 Elsevier Inc. All rights reserved.
• Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation
  作者：Nibha Mishra、D. Sasmal

  DOI：10.1016/j.bmcl.2011.02.030

  日期：2011.4

  In an effort to develop selective MAO (monoamine oxidase) B inhibitors, structure based virtual screening was initiated on an in-house library. Top 10 HITS were synthesized and evaluated for MAO (A and B) inhibitory activity, both against human and rat enzymes. All the compounds were found selective, reversible and active in nM range (100 times more potent than selegeline) towards MAO-B. Outstanding co-relation between predicted and experimental K(i) values were observed. (C) 2011 Elsevier Ltd. All rights reserved.