7-hydroxy-4'-chloroflavone | 22609-52-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-hydroxy-4'-chloroflavone
• 英文别名: 2-(4-chlorophenyl)-7-hydroxy-4H-chromen-4-one；4'-Chloro-7-hydroxyflavone；2-(4-chloro-phenyl)-7-hydroxy-chromen-4-one；2-(4-Chlor-phenyl)-7-hydroxy-chromen-4-on；2-(4-Chlorophenyl)-7-hydroxychromen-4-one
• CAS: 22609-52-5
• 化学式: C₁₅H₉ClO₃
• 分子量: 272.688
• InChiKey: OFHGICWRYGZKGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4'-chloroflavone 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 2-(4-chlorophenyl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and evaluation of novel 7-aminoalkyl-substituted flavonoid derivatives with improved cholinesterase inhibitory activities

  摘要：

  A novel series of 7-aminoalkyl-substituted flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential cholinesterase inhibitors. The results showed that most of the synthesized compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities at the micromolar range. Compound 2-(naphthalen-1-yl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4-Hchromen-4-one (5q) showed the best inhibitory activity (IC50, 0.64 mu M for AChE and 0.42 mu M for BChE) which were better than our previously reported compounds and the commercially available cholinergic agent Rivastigmine. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5q with AChE and BChE. Furthermore, molecular modeling study showed that 5q targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, these compounds (5a-5r) did not affect PC12 and HepG2 cell viability at the concentration of 10 mu M. Consequently, these flavonoid derivatives should be further investigated as multipotent agents for the treatment of Alzheimer's disease. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.031
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 硫酸 、 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 7-hydroxy-4'-chloroflavone
  参考文献：
  名称：

  有效的一锅合成和4'取代类黄酮的抗癌活性。

  摘要：

  使用修饰的Baker-Venkataraman反应，由2-羟基苯乙酮合成了许多4'-取代的（R = H，Me，Cl，F）黄酮衍生物。首次合成化合物[3-（4-氟苯甲酰基）-5-羟基-4'-氟黄酮]，产率为12％。抗增殖试验表明，合成的黄酮在4'位具有F取代基，显示出比其他黄酮衍生物更高的活性，特别是针对HeLa和MCF-7的IC 50为9.5和2.7μM。

  DOI：

  10.1134/s1070363218050328

文献信息

• Synthesis of 3-Aroylcoumarin-Flavone Hybrids
  作者：Hulluru S.P. Rao、Venkata S. Tangeti

  DOI：10.2174/157017812800167501

  日期：2012.3.1

  A facile two step synthesis of 3-aroylcoumarin-flavone hybrids was achieved from 7-hydroxyflavone and α- oxoketene dithioacetals. In the first step 7-hydroxyflavone was regioselectively formylated under Duff reaction conditions. Resulting 8-formyl-7-hydroxy flavones were condensed with α-oxoketene dithioacetals in the presence of a catalytic amount of piperidine to furnish 3-aroylcoumarin-flavone hybrids.

  一种简单的两步合成方法成功合成了3-芳酰香豆素-黄酮杂化物，反应物为7-羟基黄酮和α-氧代酮二硫代乙酰材料。在第一步中，7-羟基黄酮在Duff反应条件下进行了区域选择性醛化。生成的8-醛-7-羟基黄酮与α-氧代酮二硫代乙酰材料在催化量哌啶的存在下进行缩合，得到3-芳酰香豆素-黄酮杂化物。
• 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。
• Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor
  作者：Mahdiyeh H. S. Javadi、Aida Iraji、Maliheh Safavi、Hamed Montazeri、Parastoo Tarighi、Samane Eftekhari、Latifeh Navidpour、Seyedeh Sara Mirfazli

  DOI：10.1007/s00044-021-02767-w

  日期：2021.9

  optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound

  近年来，专注于具有选择性活性的新型强效抗癌药物是癌症治疗的最大挑战之一。乳腺癌是最常见的癌症，也是女性癌症死亡的主要原因。硫酸酯酶在将硫酸化类固醇转化为非硫酸化类固醇激素方面发挥着重要作用，这会增加许多激素依赖性癌症（如乳腺癌）的生长和发展。在这方面，进行了基于结构的优化以设计新的黄酮磺酸盐药效团作为新的类固醇硫酸酯酶抑制剂。在目前的工作中，合成 4-oxo-2-phenyl-4 H的常规方法报道了-chromen-7-yl 甲磺酸酯衍生物。它们的细胞毒性通过 MTT 测定对乳腺癌细胞系 (MCF-7) 进行评估。在雌二醇是癌细胞存活的关键生长因子的情况下，与多西紫杉醇相比，评估了最具细胞毒性的化合物3c的凋亡诱导活性，IC 50值为 0.615 µM。双染色Annexin V-FITC/PI分析结果表明该化合物3c在MCF-7细胞中的细胞毒活性通过细胞凋亡发生。进行了分子对接研究以阐明最有希望的化合物（3c）的抑制模式)
• Synthesis of Flavonoid 7-<i>O</i>-β-D-glycosides by Phase Transfer Catalysis
  作者：Zheng Wu、Ling Jiang、He Chen、Qiu-an Wang

  DOI：10.3184/030823409x431346

  日期：2009.3

  Six flavonoid 7- O-β-D-glycosides 1a-3a and 1b–3b were synthesised from the flavones 7a and 7b by glycosidation and deacetylation with the corresponding α-acetylglycosyl bromides. 7a and 7b were prepared in high yield by an improved Baker-Venkataraman rearrangement using 2, 4-dihydroxyacetophenone as starting material and tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. The glycosidation procedure was modified by using anhydrous K₂CO₃ in a solvent mixture of DMF/acetone (3:2v/v) and TBAB as a phase transfer catalyst.

  以黄酮 7a 和 7b 为原料，通过糖苷化和相应的 α-乙酰糖基溴化物脱乙酰化合成了六种黄酮 7- O-β-D 糖苷 1a-3a 和 1b-3b。以 2，4-二羟基苯乙酮为起始原料，以四丁基溴化铵（TBAB）为相转移催化剂，通过改进的贝克-文卡塔拉曼重排法高产制备了 7a 和 7b。通过在 DMF/ 丙酮（3:2v/v）混合溶剂中使用无水 K2CO3 和 TBAB 作为相转移催化剂，对糖苷化过程进行了改进。
• Antihypertensive chromonoxypropanolamines
  申请人：Pennwalt Corporation

  公开号：US04495198A1

  公开（公告）日：1985-01-22

  Chromone derivatives such as 6 or 7-(3-amino-2-hydroxypropoxy)-2-phenylchromones, -3-phenylchromones or -2,3-diphenylchromones which are useful as antihypertensive agents.

  Chromone衍生物，如6或7-(3-氨基-2-羟基丙氧基)-2-苯基色酮、-3-苯基色酮或-2,3-二苯基色酮，可用作降压剂。