3,5,7-triacetoxyflavone | 113163-70-5

• 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: 3,5,7-triacetoxyflavone
• 英文别名: 3,5,7-triacetoxy-2-phenyl-chromen-4-one；3,5,7-Triacetoxy-2-phenyl-chromen-4-on；Acetic acid 5,7-diacetoxy-4-oxo-2-phenyl-4H-chromen-3-yl ester；(3,5-diacetyloxy-4-oxo-2-phenylchromen-7-yl) acetate
• CAS: 113163-70-5
• 化学式: C₂₁H₁₆O₈
• 分子量: 396.353
• InChiKey: IIQZFVFIGAEZAD-UHFFFAOYSA-N

物化性质

• 沸点：
  561.7±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5,7-triacetoxyflavone 在 咪唑 、 苯硫酚 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以93 %的产率得到3,5-diacetoxy-7-hydroxyflavone
  参考文献：
  名称：

  신규 화합물 및 이를 포함하는 염증성 질환과 암에 대한 진단 및 치료에 사용되는 MRI 조영제

  摘要：

  本发明涉及一种含有黄酮类化合物（作为抗炎、抗氧化和抗肿瘤活性成分的天然产物之一）的新型化合物及其作为MRI造影剂的应用。本发明的新型化合物与传统的难溶性黄酮类化合物不同，基于其优异的溶解性，使其可以通过静脉注射给药。并且，该化合物在少量使用时即可预期具有抗氧化、抗炎和抗肿瘤效果，并且可以通过靶向炎症性疾病和癌症，在T1加权MRI中实现诊断与治疗的双重功能。

  公开号：

  KR20240040049A
• 作为产物：
  描述：

  sodium acetate 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸酐 作用下， 生成 3,5,7-triacetoxyflavone
  参考文献：
  名称：

  Jahns, Chemische Berichte, 1881, vol. 14, p. 2807

  摘要：

  DOI：

文献信息

• Enzyme-catalyzed alcoholysis of flavone acetates in organic solvent
  作者：Mariapina Natoli、Giovanni Nicolosi、Mario Piattelli

  DOI：10.1016/s0040-4039(00)88570-6

  日期：1990.1

  Pseudomonas sp. lipase suspended in tetrahydrofuran was used to deacylate flavone acetates. Regioselectivity of the reaction has been observed.

  假单胞菌属。悬浮在四氢呋喃中的脂肪酶用于使乙酸黄酮去酰化。已经观察到反应的区域选择性。
• 一种3,5-二乙酰氧基-7-羟基黄酮的制备方法
  申请人：武汉轻工大学

  公开号：CN111285831A

  公开（公告）日：2020-06-16

  本发明公开了一种3,5‑二乙酰氧基‑7‑羟基黄酮的制备方法，该制备方法包括：在溶剂的存在下，将3,5,7‑三乙酰氧基黄酮、吡啶盐酸盐和硅胶混合；然后，去除所述溶剂后，在第一温度下反应，得到所述3,5‑二乙酰氧基‑7‑羟基黄酮。本发明的制备方法利用硅胶和吡啶盐酸盐的协同配合作用，高选择性的对3,5,7‑三乙酰氧基黄酮的7位进行了脱乙酰化反应，没有用毒性较大的试剂，安全性高，操作简单。
• Dihydropyridine-, pyridine-, benzopyranone- and triazoloquinazoline derivatives, their preparation and their use as adenosine receptor antagonists
  申请人：The United States of America, Represented by the Secretary, Department of Health and Human Services

  公开号：EP2311806A2

  公开（公告）日：2011-04-20

  The present invention provides certain novel compounds, compositions, and a method of treating a mammal by blocking its adenosine receptors comprising administering at least one compound of the present invention. Examples of the present inventive compounds include certain flavonoids of formulae (I) and (II), wherein R1 to R4 are as defined in the description, and M is -CH (OH) -CH (R2) - or -C(OH)=C(R2)- and R1, R2 are as defined in the description; or dihydropyridines of formula (III), wherein R2 to R6 are as defined in the description; or pyridines of formula (IV), wherein R2 to R6 are as defined in the description, or triazoloquinazolines of formula (V), wherein R1 and R2 are as defined in the description; and their derivatives, or pharmaceutically acceptable salts thereof.

  本发明提供了某些新型化合物、组合物以及一种通过阻断哺乳动物的腺苷受体来治疗哺乳动物的方法，该方法包括施用至少一种本发明化合物。本发明化合物的实例包括某些式(I)和(II)的黄酮类化合物，其中R1至R4如说明中所定义，M为-CH(OH)-CH(R2)-或-C(OH)＝C(R2)-且R1、R2如说明中所定义；或式(III)的二氢吡啶类化合物，其中R2至R6如说明中所定义；或式（IV）的吡啶，其中 R2 至 R6 如说明书中定义；或式（V）的三唑并喹唑啉，其中 R1 和 R2 如说明书中定义；以及它们的衍生物或药学上可接受的盐。
• 신규 화합물 및 이를 포함하는 염증성 질환과 암에 대한 진단 및 치료에 사용되는 MRI 조영제
  申请人：주식회사 테라노큐어

  公开号：KR20240040049A

  公开（公告）日：2024-03-27

  본 발명은 항염증, 항산화, 항암 효과가 있는 천연물 중 하나인 플라보노이드를 작용기로 가진 신규 화합물 및 이를 포함하는 MRI 조영제에 관한 것이다. 본 발명의 신규 화합물은 기존의 불용성 플라보노이드와는 다른 뛰어난 용해도를 토대로 정맥 투여가 가능하며, 소량으로도 항산화, 항염 및 항암 효과를 기대할 수 있고, 염증성 질환과 암을 표적하여 진단과 치료가 동시에 가능한 T 1 MRI 조영제로 활용될 수 있다.

  本发明涉及一种含有黄酮类化合物（作为抗炎、抗氧化和抗肿瘤活性成分的天然产物之一）的新型化合物及其作为MRI造影剂的应用。本发明的新型化合物与传统的难溶性黄酮类化合物不同，基于其优异的溶解性，使其可以通过静脉注射给药。并且，该化合物在少量使用时即可预期具有抗氧化、抗炎和抗肿瘤效果，并且可以通过靶向炎症性疾病和癌症，在T1加权MRI中实现诊断与治疗的双重功能。
• Interactions of Flavonoids and Other Phytochemicals with Adenosine Receptors
  作者：Xiao-duo Ji、Neli Melman、Kenneth A. Jacobson

  DOI：10.1021/jm950661k

  日期：1996.1.1

  Flavone derivatives and other phytochemicals were found to bind to three subtypes of adenosine receptors in the micromolar range. Affinity was determined in radioligand binding assays at rat brain A(1) and A(2A) receptors using [H-3]-N-6-PIA ([H-3]-(R)-N-6-phenylisopropyladenosine) and [H-3]CGS21680 ([H-3]-2-[[4-(2-carboxyethyl)phenyl]ethyl respectively. Affinity was determined at cloned human and rat brain A(3) receptors using [I-125]-AB-MECA [N-6-(4-amino-3-iodobenzyl)adenosine-5'(N-methyluronamide)]. A structure-activity analysis indicated that the hydroxyl groups of naturally occurring flavones are not essential for affinity at adenosine receptors. Galangin, 14, displayed K-i values of 1 mu M at both rat A(1) and A(2A) receptors and 3 mu M at human A(3) receptors. Methylation but not acetylation of the hydroxyl groups of galangin enhanced A(3) affinity. Pentamethylmorin, 20, appeared to bind with 14-17-fold selectivity for human A(3) receptors vs rat A(1) and A(2A) receptors, with a K-i value of 2.65 mu M. Two flavone derivatives (14 and 15) showed 14-fold greater affinity at human vs rat A(3) receptors. Reduction of the 2,3-olefinic bond, as in (+/-)-dihydroquercetin, or glycosidation, as in robinin, greatly diminished affinity. An isoflavone, genistein, also bound only very weakly at 47 receptors. alpha-Naphthoflavone had greater receptor affinity (0.79 mu M at A(1) receptors) than the beta-isomer. Other natural products of plant origin, including oxogalanthine lactam, hematoxylin, and arborinine were found to bind to A(1) adenosine receptors with K-i values of 3-13 mu M. These findings indicate that the flavones, flavonols, flavanones, and other phytochemicals may provide leads for the development of novel adenosine antagonists. The unexpected finding of considerable affinity of flavones at both rat and human A(3) receptors may explain some of the previously observed biological effects of these compounds.