pentamethyl morin | 7555-80-8

• 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: pentamethyl morin
• 英文别名: 2-(2,4-dimethoxyphenyl)-3,5,7-trimethoxy-4H-chromen-4-one；3,5,7,2',4'-pentamethoxyflavone；2-(2,4-dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one；2-(2,4-Dimethoxy-phenyl)-3,5,7-trimethoxy-chromen-4-on；3,5,7,2',4'-Pentamethoxy-flavon；2-(2,4-Dimethoxyphenyl)-3,5,7-trimethoxychromen-4-one
• CAS: 7555-80-8
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: KPJGABLCRGWDRB-UHFFFAOYSA-N

物化性质

• 熔点：
  154-157 °C
• 沸点：
  578.9±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  pentamethyl morin 在 氢氧化钾 、 三氯化铝 、 potassium peroxomonosulphate 、 potassium carbonate 作用下， 以 吡啶 、 乙醚 、 丙酮 为溶剂， 反应 23.0h， 生成 5-hydroxy-3,7,8,2',4'-pentamethoxyflavone
  参考文献：
  名称：

  Pathak, V. P.; Khanna, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 9, p. 891 - 892

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-hydroxy-2,4,4',6'-tetramethoxychalkone 在 sodium hydroxide 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.5h， 生成 pentamethyl morin
  参考文献：
  名称：

  Pathak, V. P.; Khanna, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 9, p. 891 - 892

  摘要：

  DOI：

文献信息

• Synthesis and Biological Activities of Flavonoid Derivatives as A₃ Adenosine Receptor Antagonists
  作者：Yishai Karton、Ji-long Jiang、Xiao-duo Ji、Neli Melman、Mark E. Olah、Gary L. Stiles、Kenneth A. Jacobson

  DOI：10.1021/jm950923i

  日期：1996.1.1

  vs rat A1 or A2A receptors. The 2-styryl-6-propoxy derivative, 20, of the furanochromone visnagin was 30-fold selective for human A3 receptors vs either rat A1 or A2A receptors. Several of the more potent derivatives effectively antagonized the effects of an agonist in a functional A3 receptor assay, i.e. inhibition of adenylyl cyclase in CHO cells expressing cloned rat A3 receptors. In conclusion,

  广泛的植物化学物质筛选表明，某些黄酮和黄酮醇衍生物对 A3 腺苷受体具有相对较高的亲和力，Ki 值 > 或 = 1 microM (Ji et al. J. Med. Chem. 1996, 39, 781-788 ）。我们进一步修饰了黄酮结构，以实现对克隆人脑 A3 受体的一定程度的选择性，这是在与 [125I]AB-MECA[N6-(4-amino-3-iodobenzyl)adenosine-5'-( N-甲基脲）]。使用 [3H]-N6-PIA ([3H]-(R)-N6-苯基异丙基腺苷) 和 [3H]CGS21680 [[3H]-2-[[4] 在大鼠脑 A1 和 A2a 受体的放射性配体结合测定中确定亲和力分别为-(2-羧乙基)苯基]乙基氨基]-5'-(N-乙基氨基甲酰+++)腺苷]。黄酮醇高良姜素的三乙醚和三丙醚衍生物 4 对人 A3 受体的 Ki 值为 0.3 - 0.4 microM。
• 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。
• Herzig; Hofmann, Chemische Berichte, 1909, vol. 42, p. 157
  作者：Herzig、Hofmann

  DOI：——

  日期：——
• Structural elucidation of polymethoxyflavones from shift reagent proton NMR measurements
  作者：P. Joseph-Nathan、D. Abramo-Bruno、Ma.A. Torres

  DOI：10.1016/0031-9422(81)85114-x

  日期：1981.1
• Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2
  作者：Kapil Juvale、Katja Stefan、Michael Wiese

  DOI：10.1016/j.ejmech.2013.06.035

  日期：2013.9

  Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR. We synthesized a series of flavones, 7,8-benzoflavones and 5,6-benzoflavones with varying substituents at positions 3, 3' and 4' of the (benzo)flavone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3',4'-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations. (C) 2013 Elsevier Masson SAS. All rights reserved.