5-hydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one | 134955-46-7

• 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-hydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one
• 英文别名: 7,4'-bis(methoxymethyloxy)-5-hydroxyflavone；7,4'-bis-O-methoxymethylapigenin；7,4'-dimethoxymethylapigenin；4',7-Di-O-methoxymethyl-apigenin；5-hydroxy-7-(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]chromen-4-one
• CAS: 134955-46-7
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: OZHSNSQCAVMKSS-UHFFFAOYSA-N

物化性质

• 沸点：
  567.9±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one 在 四丁基氢氧化铵 、 N,N-二乙基苯胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 7,4'-bis-O-methoxymethyl-8-prenylapigenin
  参考文献：
  名称：

  Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study

  摘要：

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

  DOI：

  10.1021/jm040770b
• 作为产物：
  描述：

  2′,4,4′-trimethoxymethoxy-6′-hydroxychalcone 在 sodium acetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 5-hydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Fukai, Toshio; Nomura, Taro, Heterocycles, 1991, vol. 32, # 3, p. 499 - 510

  摘要：

  DOI：

文献信息

• 新的α-葡萄糖苷酶抑制剂
  申请人：中国人民解放军军事医学科学院毒物药物研究所

  公开号：CN106187970A

  公开（公告）日：2016-12-07

  本发明提供式I所示的具有选择性α-葡萄糖苷酶抑制作用的新的芹菜素类衍生物，或其药学上可接受的盐类：其中，R1和R2各自独立地为H或-(CH2)nCOOR3；R3为H，或C1-C5的直链或支链烷基；n为1-10的整数；R1和R2相同或不同，但是R1和R2不能同时为H。
• Discovery of xanthine oxidase inhibitors and/or α-glucosidase inhibitors by carboxyalkyl derivatization based on the flavonoid of apigenin
  作者：Zhuo-Ran Su、Shi-Yong Fan、Wei-Guo Shi、Bo-Hua Zhong

  DOI：10.1016/j.bmcl.2015.05.016

  日期：2015.7

  Three series of apigenin derivatives have been prepared by coupling the carboxyl alkyl group to 4'-, 5- or 7-hydroxyl groups of apigenin respectively. Preliminary biological evaluation in vitro revealed that xanthine oxidase inhibitory activity was improved by modifications at 4'-position and decreased by similar modifications at 5-, 7-positions while alpha-glucosidase inhibitory activity was maintained by modifications at 5-, 7-positions but lost by modifications at 4'-position. Administration (ip) of 7e markedly lowered serum uric acid levels in potassium oxonate induced hyperuricemic mouse model and administration (p.o.) of 11d or 11e effectively suppressed the elevation of serum glucose in the oral sucrose tolerance test in mice, while apigenin were not significantly effective in both tests. (C) 2015 Elsevier Ltd. All rights reserved.
• Potent, Selective, Allosteric Inhibition of Human Plasmin by Sulfated Non-Saccharide Glycosaminoglycan Mimetics
  作者：Daniel K. Afosah、Rami A. Al-Horani、Nehru Viji Sankaranarayanan、Umesh R. Desai

  DOI：10.1021/acs.jmedchem.6b01474

  日期：2017.1.26

  Although plasmin inhibitors could be used in multiple disorders, their use has been restricted to preventing blood loss in hemostatic dysregulation because of poor efficacy and adverse effects of current agents. We reasoned that a new class of direct inhibitors that offer better efficacy, selectivity, and safety could be discovered by exploiting allosterism in plasmin, a protease homologous to other allosteric serine proteases. We report on the synthesis, biological activity, and mechanism of action of a group of small molecules, called non-saccharide glycosaminoglycan mimetics (NSGMs), as direct allosteric plasmin inhibitors. Our results show that distinct NSGMs selectively inhibit human fall-length plasmin. The molecule inhibited clot lysis, alluding to its promise as an allosteric regulator of plasmin. We show that direct allosteric inhibition of plasmin could led to new antifibrinolytic agent(s) that may exhibit better efficacy, potency, selectivity, and safety in comparison to current therapy.
• Inhibition of Herpes Simplex Virus-1 Entry into Human Cells by Nonsaccharide Glycosaminoglycan Mimetics
  作者：Rahaman Navaz Gangji、Nehru Viji Sankaranarayanan、James Elste、Rami A. Al-Horani、Daniel K. Afosah、Rachel Joshi、Vaibhav Tiwari、Umesh R. Desai

  DOI：10.1021/acsmedchemlett.7b00364

  日期：2018.8.9

  Although heparan sulfate (HS) has been implicated in facilitating entry of enveloped viruses including herpes simplex virus (HSV), small molecules that effectively compete with this abundant, cell surface macromolecule remain unknown. We reasoned that entry of HSV-1 involving its glycoprotein D (gD) binding to HS could be competitively targeted through small, synthetic, nonsaccharide glycosaminoglycan mimetics (NSGMs). Screening a library of NSGMs identified a small, distinct group that bound gD with affinities of 8-120 nM. Studies on HSV-1 entry into HeLa, HFF-1, and VK2/E6E7 cells identified inhibitors with potencies in the range of 0.4-1.0 mu M. These synthetic NSGMs are likely to offer promising chemical biology probes and/or antiviral drug discovery opportunities.
• Designing Synthetic, Sulfated Glycosaminoglycan Mimetics That Are Orally Bioavailable and Exhibiting <i>In Vivo</i> Anticancer Activity
  作者：Shravan Morla、Ongolu Ravikumar、Connor O’Hara、Rio Boothello、Alberto Vera、Elsamani I. Abdelfadiel、Rawan Fayyad、Daniel K. Afosah、Chetna Sharon、Leopoldo Fernandez、Syed Ammer Shah、Bhaumik B. Patel、Umesh R. Desai

  DOI：10.1021/acs.jmedchem.2c01511

  日期：2023.1.26