2’,4’-二羟查耳酮 | 1776-30-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 2’,4’-二羟查耳酮
• 中文别名: 2',4'-二羟查耳酮；2`,4`-二羟查耳酮
• 英文名称: 2',4'-dihydroxychalcone
• 英文别名: 2′,4′-dihydroxychalcone；2’,4’-dihydroxy chalcone；2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-phenyl-；1-(2,4-dihydroxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 1776-30-3
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: JUMSUVHHUVPSOY-UHFFFAOYSA-N

物化性质

• 熔点：
  170°C
• 沸点：
  453.5±38.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 稳定性/保质期：
  常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  放入密闭的储存容器中，并保持密封，存放在阴凉干燥处，远离氧化剂。

反应信息

• 作为反应物：
  描述：

  2’,4’-二羟查耳酮 在 sodium hydroxide 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以48%的产率得到7-羟基黄烷酮
  参考文献：
  名称：

  7-Hydroxyflavanone (I) and 7-Ethoxycarbonylmethoxyflavanone (II)

  摘要：

  The gamma-pyrone rings in both of the title molecules, 2,3-dihydro-7-hydroxy-2-phenyl-4H- 1-benzopyran-4-one, C15H12O3, (I), and ethyl (2,3-dihydro-2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyacetate, C19H18O5, (II), adopt a C(2)-sofa conformation. In (I), the phenyl ring is twisted 103.0 (1)degrees from the plane of the fused rings and the hydroxy group at C(7) forms an intermolecular hydrogen bond to O(4) of the adjacent molecule. In (II), the phenyl ring is twisted 121.5 (2)degrees from the plane of the fused rings and the acetyl group is oriented slightly out of the plane of the benzene ring.

  DOI：

  10.1107/s0108270195002940
• 作为产物：
  描述：

  1-[4-(benzyloxy)-2-hydroxyphenyl]-3-phenyl-2-propen-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.75h， 以52%的产率得到2’,4’-二羟查耳酮
  参考文献：
  名称：

  Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

  摘要：

  Eleven 4'-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 mu M. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the a, beta-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

  DOI：

  10.1016/j.bmc.2018.10.045

文献信息

• Arylalkyl Ketones, Benzophenones, Desoxybenzoins and Chalcones Inhibit TNF-α Induced Expression of ICAM-1: Structure-Activity Analysis
  作者：Sarvesh Kumar、Chandra Shekhar Reddy L、Yogesh Kumar、Amit Kumar、Brajendra K. Singh、Vineet Kumar、Shashwat Malhotra、Mukesh K. Pandey、Rajni Jain、Rajesh Thimmulappa、Sunil K. Sharma、Ashok K. Prasad、Shyam Biswal、Erik Van der Eycken、Anthony L. DePass、Sanjay V. Malhotra、Balaram Ghosh、Virinder S. Parmar

  DOI：10.1002/ardp.201100279

  日期：2012.5

  potent intercellular cell adhesion molecule‐1 (ICAM‐1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM‐1 inhibitory activity. The structure‐activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism

  白细胞和血管内皮细胞 (EC) 之间通过细胞粘附分子的相互作用在各种炎症和自身免疫性疾病的发病机制中起着重要作用。阻断这些相互作用的小分子已成为针对急性和慢性炎症疾病的潜在治疗剂。为了鉴定有效的细胞间细胞粘附分子-1 (ICAM-1) 抑制剂，已经合成了大量的芳烷基酮、二苯甲酮、脱氧安息香和查耳酮及其类似物（共 54 种），并筛选了它们的 ICAM-1 抑制剂活动。这些化合物的构效关系研究确定了三种有效的查耳酮衍生物，并证明了其 ICAM-1 抑制活性的可能机制。
• Biocatalytic green alternative to existing hazardous reaction media: synthesis of chalcone and flavone derivatives <i>via</i> the Claisen–Schmidt reaction at room temperature
  作者：Kashyap J. Tamuli、Ranjan K. Sahoo、Manobjyoti Bordoloi

  DOI：10.1039/d0nj03839c

  日期：——

  Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon–carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催
• Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
  作者：Joan Villena、Iván Montenegro、Bastian Said、Enrique Werner、Susana Flores、Alejandro Madrid

  DOI：10.1016/j.fct.2021.111969

  日期：2021.2

  This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0-94.0%) of eighteen oxyalkylated derivatives of 2',4'-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive

  这项工作报告了一种高效，环保的超声辅助方法的开发，该方法可以高产率地合成18种2'，4'-二羟基查耳酮的烷氧基化衍生物（70.0-94.0％）。对合成的化合物进行了针对HT-29（结肠直肠），MCF-7（乳腺癌）和PC-3（前列腺）人类肿瘤细胞系的体外生物学分析，这些细胞系是世界上诊断出的十种最具侵袭性的恶性肿瘤之一。细胞毒性评估表明，四种合成的化合物对MCF-7（IC 50 = 8.4–34.3μM）和PC-3（IC 50 = 9.3-29.4μM）表现出中等至非常高的毒性，与5-氟尿嘧啶（IC 5016.4–22.3μM）。相同的化合物仅对HT-29（IC 50 15.3-36.3μM）具有中等活性，接近柔红霉素（IC 50 15.1μM ）。接着，尽管化合物的选择性指数（SI）较弱，但化合物18对癌细胞显示出显着的选择性细胞毒性活性（5.8-10.57）。除此以外，大多数化合物显着降
• Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters
  作者：Jae-Ho Jeon、Deok-Mo Yang、Jong-Gab Jun

  DOI：10.5012/bkcs.2011.32.1.65

  日期：2011.1.20

  Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。
• Cyclization of 2′-hydroxychalcones to flavones using ammonium iodide as an iodine source: An eco-friendly approach
  作者：Pramod Kulkarni、Dasharath Kondhare、Ravi Varala、Pudukulathan Zubaidha

  DOI：10.2298/jsc120901119k

  日期：——

  Ammonium iodide in open air decomposes to ammonia and iodine. The in situ generated iodine has been used for cyclization of 2?-hydroxychalcones to corresponding flavones under solvent free conditions with good to excellent yields. This method would serve as an attractive alternative to the existing methods for synthesis of flavones and use of toxic molecular iodine is avoided.

  碘化铵在露天会分解成氨和碘。原位生成的碘 生成的碘被用于在无溶剂条件下将 2? 在无溶剂条件下环化成相应的黄酮类化合物，并获得良好甚至极好的产率。 产率。这种方法可以替代现有的 黄酮合成方法的一种有吸引力的替代方法，而且可以避免使用有毒的碘分子。 避免使用有毒的分子碘。