CAS: 798-61-8; 6,7-Dimethoxy-3-(4-Methoxyphenyl)-4H-Chromen-4-One

该化合物是一种合成的甲状腺素衍生物,其特点是其核心结构有3个甲基氧功能组,该化合物因其结构上与自然产生的甲状腺素相似而显示出潜在的生物活动,该物质因与雌激素受体和抗氧化性特性相互作用而闻名;其甲氧代谢替代物可增强代谢稳定性和亲脂性,使其成为药理学和生物化学研究研究的候选体. 三甲基氧基索福拉夫酮可作为合成更复杂的生物活性分子的宝贵中间体或分析应用中的参考标准.需要进一步调查,以充分阐明其机械路径和应用.

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物理性质

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CAS号75199-40-5 3-(4-hydroxyphe... | CAS号77-78-1 硫酸二甲酯 | CAS号290-87-9 1,3,5-三嗪 | CAS号5128-49-4 1-(2-hydroxy-4,... | CAS号68-12-2 N,N-二甲基甲酰胺 | CAS号17817-31-1 6,7,4'-三羟基异黄酮 | CAS号74-88-4 碘甲烷

合成工艺路线路线简述

  • 1903769-56-1 = 798-61-8
    反应条件:1.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    75199-40-5 = 798-61-8
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; 3 H,70 °C
    标题:Antimicrobial And Antioxidant Isoflavonoid Derivatives From The Roots Of Amphimas Pterocarpoides
    作者:Saah,Edwige P. Fodja; Et Al
    参考文献:Zeitschrift Fuer Naturforschung 日期:2013 卷标:68(8) 页码:931-938]

    40957-83-3 = 798-61-8
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 12 H,Rt
    标题:Biotransformation Of Isoflavones By The Larvae Of The Common Cutworm (Spodoptera Litura)
    作者:Takahashi,Koji; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2006 卷标:54(5) 页码:719-721]

    5392-10-9 = 798-61-8
    反应条件:1.1 Solvents: Diethyl Ether,Tetrahydrofuran; Rt; 2 H,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Cooled2.1 Reagents: Pyridinium Chlorochromate Solvents: Dichloromethane; 18 H,Rt3.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt4.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt5.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C5.2 Reagents: Sodium Bicarbonate Solvents: Water6.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    120-14-9 = 798-61-8
    反应条件:1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide; 0 °C; 8 H,Rt2.1 Solvents: Diethyl Ether,Tetrahydrofuran; Rt; 2 H,Rt2.2 Reagents: Ammonium Chloride Solvents: Water; Cooled3.1 Reagents: Pyridinium Chlorochromate Solvents: Dichloromethane; 18 H,Rt4.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt4.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt5.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt6.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C6.2 Reagents: Sodium Bicarbonate Solvents: Water7.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    93-15-2 = 798-61-8
    反应条件:1.1 Reagents: Potassium Hydroxide; 40 Min,100 °C1.2 Reagents: Pyridine,Ozone Solvents: Methanol,Chloroform; 1 - 2 H,15 °C2.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide; 0 °C; 8 H,Rt3.1 Solvents: Diethyl Ether,Tetrahydrofuran; Rt; 2 H,Rt3.2 Reagents: Ammonium Chloride Solvents: Water; Cooled4.1 Reagents: Pyridinium Chlorochromate Solvents: Dichloromethane; 18 H,Rt5.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt5.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt6.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt7.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C7.2 Reagents: Sodium Bicarbonate Solvents: Water8.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    104-01-8 + 2033-89-8 = 798-61-8
    反应条件:1.1 Catalysts: Boron Trifluoride Etherate; 10 Min,120 °C; 120 °C -> Rt1.2 10 Min,50 °C1.3 Reagents: Methanesulfonyl Chloride; 30 Min,80 °C
    标题:Synthesis Of Various Kinds Of Isoflavones,Isoflavanes,And Biphenyl-Ketones And Their 1,1-Diphenyl-2-Picrylhydrazyl Radical-Scavenging Activities
    作者:Goto,Hideyuki; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2009 卷标:57(4) 页码:346-360]

    = 798-61-8
    反应条件:1.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    = 798-61-8
    反应条件:1.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt2.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C2.2 Reagents: Sodium Bicarbonate Solvents: Water3.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    74746-10-4 + 123-11-5 = 798-61-8
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt2.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt3.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C3.2 Reagents: Sodium Bicarbonate Solvents: Water4.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    140-67-0 = 798-61-8
    反应条件:1.1 Reagents: Potassium Hydroxide; 40 Min,100 °C1.2 Reagents: Pyridine,Ozone Solvents: Methanol,Chloroform; 1 - 2 H,15 °C2.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt3.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt4.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C4.2 Reagents: Sodium Bicarbonate Solvents: Water5.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438]

    5293-52-7 = 798-61-8
    反应条件:1.1 Reagents: Pyridinium Chlorochromate Solvents: Dichloromethane; 18 H,Rt2.1 Reagents: Sodium Hydroxide Solvents: Ethanol; 20 °C; 6 H,Rt; Overnight,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Ph 3 - 4,Rt3.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Ethanol,Water; Rt; 3 H,30 °C; 24 H,Rt; 30 H,Rt4.1 Catalysts: Boron Trifluoride Etherate Solvents: Dichloromethane; 0 °C; 3 H,20 °C4.2 Reagents: Sodium Bicarbonate Solvents: Water5.1 Reagents: Picolinic Acid,Potassium Carbonate Catalysts: Cuprous Iodide Solvents: Dimethylformamide; 8 H,135 - 140 °C
    标题:Efficient Synthesis Of Glaziovianin A Isoflavone Series From Dill And Parsley Extracts And Their In Vitro/in Vivo Antimitotic Activity
    作者:Semenov,Victor V.; Et Al
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(5) 页码:1429-1438
📜1-(2-Bromo-4,5-Dimethoxyphenyl)Ethanone置于2-吡啶甲酸,Copper(L) Iodide,三氟化硼乙醚,双氧水,Potassium Carbonate,Sodium Hydroxide体系中,用 乙醇,二氯甲烷,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 74.0H,反应生成 4',6,7-三甲氧基异黄酮
参考文献:从莳萝和欧芹提取物中高效合成glaziovianin A异黄酮系列及其体外/体内抗有丝分裂活性
标题:从莳萝和欧芹提取物中高效合成glaziovianin A异黄酮系列及其体外/体内抗有丝分裂活性
摘要:开发了一种简明的六步方案,从莳萝和香菜种子中容易获得的植物代谢物开始合成异黄酮glaziovianin A(gva)及其烷氧基苯基衍生物9.反应顺序包括将关键的中间环氧化物7有效转化为相应的β-酮醛8,然后将它们的cu(i)介导的环化反应转化为目标序列9.使用一组七种人类癌细胞系和体内海胆胚胎测定法评估了gva及其衍生物的生物活性.两个筛选平台均证实了亲本gva(9Cg)及其烷氧基衍生物.结构与活性之间的关系研究表明,分别被三甲氧基和莳萝酚衍生的b环取代的化合物9Cd和9Cf的活性低于母体9Cg.在评估的人类癌细胞系中,A375黑色素瘤细胞系对被测分子最敏感.值得注意的是,目标化合物对浓度高达10μm的人外周血单核细胞没有细胞毒性.海胆测定的表型读数明确表明异黄酮9Cg,9Cd和9Cf具有直接的微管破坏作用.
DOI:10.1021/acs.Jnatprod.6B00173

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主要参考文献

参考标题:Synthesis Of Various Kinds Of Isoflavones, Isoflavanes, And Biphenyl-Ketones And Their 1,1-Diphenyl-2-Picrylhydrazyl Radical-Scavenging Activities
作者:Hideyuki Goto,Yoshiyasu Terao,Shuji Akai
摘要:Forty-Eight Kinds Of Isoflavones (8), Thirty-One Isoflavanes (9), And Forty-Seven Biphenyl-Ketones (10, 10′) Were Synthesized From Eleven Kinds Of Substituted Phenols (11) And Six Phenylacetic Acids (12). Among Them, Seventy-Five Compounds Are New. The Radical Scavenging Activities Of These Compounds Were Evaluated Using 1,1-Diphenyl-2-Picrylhydrazyl (Dpph) At Ph 6.0. We Found That Thirty-Nine Out Of Forty-Three Compounds Having A Catechol Moiety On Either The A- Or The B-Ring Exhibited A High Activity (Ed50=12-54 μm) Similar To That Of Catechin. In These Cases, The Remaining Part Of Their Structure Seemed To Have Little Effect On Their Activity. Many 6- Or 8-Hydroxyisoflavanes (9E-I) And Their Biphenyl-Ketone Derivatives (10E-H) Also Showed A High Activity (Ed50=<50 μm), While All Of Their Corresponding Isoflavones (8E-I) Were Not Active At All. The 7-Hydroxyisoflavanes Having Either An Additional Hydroxyl Group At The C5-Position (9D) Or A Methoxy Group At The C6-Position (9J) Presented A High Activity (Ed50=26-32 μm). This Study Suggests That Natural Isoflavones Have The Possibilities Of Exhibiting Antioxidant Activities Through The Hydroxylation At The C6-, C8-, Or C3′-Position Or The Formation Of The Isoflavanes (9) And/or The Biphenyl-Ketone Derivatives (10′) By Metabolism Or Biotransformation.

合成参考文献


参考文献:10.1107/s010827019200249x
摘要:Shoja M. 4',6,7-Trimethoxyisoflavone. Acta Crystallogr C Cryst Struct Commun. 1992 Nov 15;48(11):2033–5. doi: 10.1107/s010827019200249x.
参考文献:10.1186/s13765-022-00764-0
摘要:Choi J, Kim Y, Cho M. Therapeutic effects of TMF and catechol in pulmonary fibrosis: in vitro and in vivo analysis. Appl Biol Chem. 2023 Feb 01;66(1). doi: 10.1186/s13765-022-00764-0.
参考文献:10.1186/s13765-025-01007-8
摘要:Abeysiriwardhana HNI, Choi J, Anandappa JM, Malla A, Cho M. Design, synthesis, and biological evaluation of ACF-03: a novel anti-fibrotic and antioxidant agent targeting ROS-TGF-β1-HIF-1α axis. Appl Biol Chem. 2025 Jul 30;68(1). doi: 10.1186/s13765-025-01007-8.
参考文献:10.1186/s13765-025-01061-2
摘要:Yang SH, Kim JS, Kim DK, Yoon TH, Cho M, Cho SK. ACF-01 enhances the anticancer effect of doxorubicin by suppressing stemness and inducing apoptosis in triple-negative breast cancer stem-like cells. Appl Biol Chem. 2025 Nov 24;68(1). doi: 10.1186/s13765-025-01061-2.
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