5,7,3',4'-O-tetramethylrutin | 58528-03-3

• 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: 5,7,3',4'-O-tetramethylrutin
• 英文别名: 3-[[6-O-(6-Deoxy-I+/--L-mannopyranosyl)-I(2)-D-glucopyranosyl]oxy]-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one；2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• CAS: 58528-03-3
• 化学式: C₃₁H₃₈O₁₆
• 分子量: 666.633
• InChiKey: MEJNXDYVXPUWEN-MVXJRKCZSA-N

物化性质

• 沸点：
  908.9±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  225.43
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  5,7,3',4'-O-tetramethylrutin 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-羟基-3,4,5,7-四甲氧基黄酮
  参考文献：
  名称：

  含有1,3,4-恶二唑部分的新型2-苯基-4H-色酮衍生物的合成、端粒酶抑制和抗癌活性

  摘要：

  摘要 根据先前的研究，制备了 66 种含有酰胺和 1,3,4-恶二唑部分的 2-苯基-4H-色酮衍生物作为潜在的端粒酶抑制剂。结果显示大多数标题化合物对端粒酶表现出显着的抑制活性。其中，一些化合物表现出最有效的端粒酶抑制活性（IC 50 < 1 µM），明显优于星形孢菌素（IC 50 = 6.41 µM）。此外，总结了清晰的构效关系，表明甲氧基的取代以及苯环上取代基的位置、类型和数量对端粒酶活性有显着影响。其中，化合物A33对端粒酶有显着的抑制作用。流式细胞仪分析表明，化合物A33可以将MGC-803细胞周期阻滞在G2/M期，并以浓度依赖性方式诱导细胞凋亡。同时，Western blotting 显示该化合物可以降低作为端粒酶片段的dyskerin 的表达。

  DOI：

  10.1080/14756366.2020.1864630
• 作为产物：
  描述：

  硫酸二甲酯 、 芦丁 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 49.0h， 生成 5,7,3',4'-O-tetramethylrutin
  参考文献：
  名称：

  新型2-苯基-4H-色烯衍生物：体外和体内的合成和抗炎活性评价

  摘要：

  摘要 设计、合成和优化具有更好抗炎活性的黄酮衍生物具有重要意义。本研究旨在设计合成一系列具有抗炎作用的新型2-苯基-4H-chromen-4-one化合物；其中，化合物8被认为是最好的化合物。然后，在体内研究了化合物8对TLR4/MAPK信号通路的影响，结果表明化合物8可以下调NO、IL-6和TNF-α的表达，并通过抑制LPS诱导的炎症反应来抑制LPS诱导的炎症反应。 TLR4/MAPK 通路。此外，化合物8通过 LPS 诱导的体内炎症疾病小鼠模型减轻炎症. 结果表明，化合物8通过调节 TLR4/MAPK 途径具有抗炎症的潜力，可以进一步评估药物开发。

  DOI：

  10.1080/14756366.2022.2124983

文献信息

• 黄酮类芳香化酶抑制剂及其制备方法与应用
  申请人：天津科技大学

  公开号：CN108276374B

  公开（公告）日：2020-01-31

  本发明涉及一系列黄酮类芳香化酶抑制剂，通过氰甲基化反应和烷基化反应，改变了黄酮类化合物母环上的某些取代基团，合成出一系列黄酮类化合物及其衍生物。其结构通式可用权利要求书中通式表示。结构通式中，R1选自‑OH或H中的任意一种，R2选自‑H或‑OCH3或‑OH中的任意一种,R3选自‑H、‑OH或‑OCH2CN或‑OCH3中的任意一种；R4选自‑H或‑OH或‑OCH2Ph或‑2‑（2‑甲氧基‑2氧代乙基）苄氧基中的任意一种，R5选自‑H或‑OCH2Ph或‑OCH3中的任意一种，R6选自‑H或‑OH或‑OCH3中的任意一种。这些黄酮类化合物对芳香化酶有较好的抑制作用，经过活性测试，本抑制剂抑制芳香化酶的活性最高为IC50=0.251µmol/L。
• Synthesis and Anti-hypertensive Effects of the Twin Drug of Nicotinic Acid and Quercetin Tetramethyl Ether
  作者：Zhonglei Wang、Liyan Yang、Shuai Cui、Yingxi Liang、Xiaohua Zhang

  DOI：10.3390/molecules19044791

  日期：——

  A novel twin drug consisting of nicotinic acid (VB3) and quercetin tetramethyl ether (QTME) has been synthesized as an antihypertensive in a total yield of 79.2% through methylation, hydrolysis, acylation and esterification starting from rutin. The structures of synthesized compounds were elucidated by 1H-NMR, 13C-NMR and elemental analysis. The anti-hypertensive effects of an oral daily dose (15 mg/kg) of the synthesized compounds in spontaneously hypertensive (SHR) rats and normotensive Wistar Kyoto (WKY) rats were analysed. The data demonstrate that the twin drug VB3-QTME both reduces the elevated blood pressure and prolongs the action time in SHR rats without effect on WKY rats. However, definitive evidence of a precise mechanism of action by which VB3-QTME might decrease blood pressure remains elusive. Based on the results, the therapeutic potential of this twin drug is discussed.

  从芦丁开始，通过甲基化、水解、酰化和酯化，合成了一种由烟酸（VB3）和槲皮素四甲基醚（QTME）组成的新型孪生药物，总收率为 79.2%。通过 1H-NMR、13C-NMR 和元素分析阐明了合成化合物的结构。分析了自发性高血压（SHR）大鼠和血压正常的 Wistar Kyoto（WKY）大鼠每日口服（15 mg/kg）合成化合物的抗高血压作用。数据表明，孪生药物 VB3-QTME 既能降低 SHR 大鼠升高的血压，又能延长其作用时间，但对 WKY 大鼠没有影响。然而，VB3-QTME 降低血压的确切作用机制仍未确定。基于这些结果，我们讨论了这种孪生药物的治疗潜力。
• Nitrogen-containing derivatives of O-tetramethylquercetin: Synthesis and biological profiles in prostate cancer cell models
  作者：Pravien Rajaram、Ziran Jiang、Guanglin Chen、Alyssa Rivera、Alison Phasakda、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.bioorg.2019.03.047

  日期：2019.6

  Forty-eight nitrogen-containing quercetin derivatives were synthesized from readily available rutin or quercetin for the in vitro evaluation of their biological profiles. The WST-1 cell proliferation assay data indicate that thirty-nine out of the forty-eight derivatives possess significantly improved antiproliferative potency as compared with quercetin and fisetin, as well as the parent 3,3',4',7-O-tetramethylquercetin toward both androgen-sensitive (LNCaP) and androgen-insensitive (PC-3 and DU145) human prostate cancer cell lines. 5-O-Aminoalkyl-3,3',4',7-O-tetramethylquercetins were established as a better scaffold for further development as anti-prostate cancer agents. Among them, 5-O-(N,N-dibutylamino)propyl-3,3',4',7-O-tetramethylquercetin (44) was identified as the optimal derivative with IC(50 )values of 0.55-2.82 mu M, being over 35-182 times more potent than quercetin. The flow cytometry-based assays further demonstrate that 44 effectively activates PC-3 cell apoptosis.
• Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety
  作者：Yu Han、Yan Ding、Dandan Xie、Deyu Hu、Pei Li、Xiangyang Li、Wei Xue、Linhong Jin、Baoan Song

  DOI：10.1016/j.ejmech.2015.01.017

  日期：2015.3

  Rutin (compound 5) and some compounds (compounds 1-4 and 6) were isolated from Artemisia princeps Pamp (A. prirtceps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy (H-1 NMR), carbon nuclear magnetic resonance spectroscopy (C-13 NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 mu g/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 mu g/mL, which was better than that of Ningnanmycin (432.22 mu g/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis of methylated quercetin derivatives and their reversal activities on P-gp- and BCRP-mediated multidrug resistance tumour cells
  作者：Jian Yuan、Iris L.K. Wong、Tao Jiang、Si Wen Wang、Tao Liu、Bin Jin Wen、Larry M.C. Chow、Biao Wan Sheng

  DOI：10.1016/j.ejmech.2012.05.026

  日期：2012.8

  Three methylated quercetins and a series of O-3 substituted 5,7,3',4'-tetra-O-methylated quercetin derivatives have been synthesized and evaluated on the modulating activity of P-gp, BCRP and MRP1 in cancer cell lines. Compound 17 (with a 2-((4-methoxybenzoyl)oxy)ethyl at O-3) is the most potent P-gp modulator. Three derivatives, compound 9 (3,7,3',4'-tetra-O-methylated quercetin), compound 14 (with a 2-((3-oxo-3-(3,4,5trimethoxyphenyl)prop-1-en-1-yl)oxy)ethyl at O-3) and compound 17, consistently exhibited promising BCRP-modulating activity. Interestingly, compound 17 was found to be equipotent against both P-gp and BCRP Importantly, these synthetic quercetin derivatives did not exhibit any inherent cytotoxicity to cancer cell lines or normal mouse fibroblast cell lines. These quercetin derivatives can be employed as safe and effective modulators of P-gp- or BCRP-mediated drug resistance in cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.