CAS: 85157-21-7; 2-(7-Amino-2-Oxo-2H-Chromen-4-yl)Acetic Acid

该化合物是一种含有碳酸功能组的coumarin衍生物,为进一步的化学修改提供了多种反应功能.其结构特征,包括氨基和碳基组,使其成为有机合成中的宝贵中间体,特别是用于建造热循环化合物或荧光探测器.化合物的铬-2-1-1核心有助于潜在的光物理特性,在传感器或生物成像等应用中有用.乙酸会增强极地溶剂的溶性,便于其在水相反应中使用.该化合物因其平衡的再活动性和功能组的兼容性,非常适合医学化学和材料科学的研究.

结构式图片

物理性质

MSDS等安全信息

上下游产品

CAS号85157-20-6 ethyl 7-N-(carb... | CAS号343310-64-5 2-(7-((乙氧基羰基)氨基... | CAS号7159-96-8 N-(3-羟苯基)氨基甲酸乙酯 | CAS号591-27-5 间氨基苯酚 | CAS号105-50-0 丙酮二羧酸二乙酯 | CAS号1830-54-2 1,3-丙酮二羧酸二甲酯 | CAS号542-05-2 1,3-丙酮二羧酸 | CAS号77-92-9 柠檬酸 | CAS号378247-75-7 [7-(9H-芴-9-基甲氧基...

合成工艺路线路线简述

  • 343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 24 H,Reflux; 0 °C1.2 Reagents: Sulfuric Acid Solvents: Water; Ph 2,0 °C1.3 Reagents: Water; Cooled; Rt
    标题:A Versatile Access To New Halogenated 7-Azidocoumarins For Photoaffinity Labeling: Synthesis And Photophysical Properties
    作者:Paunescu,Emilia; Louise,Ludivine; Jean,Ludovic; Romieu,Anthony; Renard,Pierre-Yves
    参考文献:Dyes And Pigments 日期:2011 卷标:91(3) 页码:427-434]

    85157-20-6 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 16 H,Reflux; Reflux -> Rt1.2 Reagents: Sulfuric Acid Solvents: Water; Ph 2,Rt
    标题:A Multifunctional Bioconjugate Module For Versatile Photoaffinity Labeling And Click Chemistry Of Rna
    作者:Kellner,Stefanie; Seidu-Larry,Salifu; Burhenne,Juergen; Motorin,Yuri; Helm,Mark
    参考文献:Nucleic Acids Research 日期:2011 卷标:39(16) 页码:7348-7360]

    105-50-0 = 85157-21-7
    反应条件:1.1 Reagents: Ethyl Chloroformate Solvents: Ethyl Acetate; 30 Min,Reflux; 1 H,Reflux1.2 Reagents: Sulfuric Acid Solvents: Water; Rt; Overnight,Rt1.3 Solvents: Water; Cooled1.4 Reagents: Sodium Hydroxide Solvents: Water; 2 H,Reflux; Reflux -> 0 °C1.5 Reagents: Sulfuric Acid; Ph 2
    标题:Genetically Encoded Fluorescent Unnatural Amino Acids And Fret Probes For Detecting Deubiquitinase Activities
    作者:Li,Manjia; Wang,Feifei; Yan,Long; Lu,Minghao; Zhang,Yuqing; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2022 卷标:58(73) 页码:10186-10189]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Overnight,Reflux; Cooled1.2 Reagents: Sulfuric Acid Solvents: Water; Ph 2,Cooled
    标题:Marine Natural Products As Inhibitors Of Cystathionine Beta-Synthase Activity
    作者:Thorson,Megan K.; Van Wagoner,Ryan M.; Harper,Mary Kay; Ireland,Chris M.; Majtan,Tomas; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2015 卷标:25(5) 页码:1064-1066]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide; 12 H,Reflux
    标题:Molecularly Engineered Quantum Dots For Visualization Of Hydrogen Sulfide
    作者:Yan,Yehan; Yu,Huan; Zhang,Yajiao; Zhang,Kui; Zhu,Houjuan; Et Al
    参考文献:Acs Applied Materials & Interfaces 日期:2015 卷标:7(6) 页码:3547-3553]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Ph 14,100 °C
    标题:Hydrophilic Photolabeling Of Glycopeptides From The Murine Liver-Intestine (Li) Cadherin Recognition Domain
    作者:Heiner,Sebastian; Detert,Heiner; Kuhn,Axel; Kunz,Horst
    参考文献:Bioorganic & Medicinal Chemistry 日期:2006 卷标:14(18) 页码:6149-6164]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water1.2 Reagents: Sulfuric Acid
    标题:Expedient Solid-Phase Synthesis Of Fluorogenic Protease Substrates Using The 7-Amino-4-Carbamoylmethylcoumarin (Acc) Fluorophore
    作者:Maly,Dustin J.; Leonetti,Francesco; Backes,Bradley J.; Dauber,Deborah S.; Harris,Jennifer L.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(3) 页码:910-915]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 3 H,Reflux1.2 Reagents: Sulfuric Acid; Ph 2,0 °C
    标题:O-Fluorination Of Aromatic Azides Yields Improved Azido-Based Fluorescent Probes For Hydrogen Sulfide: Synthesis,Spectra,And Bioimaging
    作者:Wei,Chao; Wang,Runyu; Wei,Lv; Cheng,Longhuai; Li,Zhifei; Et Al
    参考文献:Chemistry - An Asian Journal 日期:2014 卷标:9(12) 页码:3586-3592]

    7159-96-8 + 77-92-9 = 85157-21-7
    反应条件:1.1 Reagents: Sulfuric Acid1.2 Reagents: Acetic Acid,Sulfuric Acid1.3 Reagents: Ammonium Hydroxide Solvents: Water
    标题:Bifunctional Coumarin Derivatives In Solution And Solid Phase Synthesis Of Fluorogenic Enzyme Substrates
    作者:Charitos,Christos; Kokotos,George; Tzougraki,Chryssa
    参考文献:Journal Of Heterocyclic Chemistry 日期:2001 卷标:38(1) 页码:153-158]

    343310-64-5 = 85157-21-7 [标题:Reaction Conditions
    标题:Chromogenic Anticounterfeit And Security Papers: An Easy And Effective Approach
    作者:Guirado-Moreno,Jose Carlos; Guembe-Garcia,Marta; Garcia,Jose M.; Aguado,Roberto; Valente,Artur J. M.; Et Al
    参考文献:Acs Applied Materials & Interfaces 日期:2021 卷标:13(50) 页码:60454-60461]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide; Reflux
    标题:Use Of A Small Molecule As An Initiator For Interchain Staudinger Reaction: A New Atp Sensing Platform Using Product Fluorescence
    作者:Yu,Huan; Zheng,Jing; Yang,Sheng; Asiri,Abdullah M.; Alamry,Khalid A.; Et Al
    参考文献:Talanta 日期:2018 卷标:178 页码:282-286]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; Overnight,Rt -> Reflux1.2 Reagents: Water1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Ubiquitin 7-Amino-4-Carbamoylmethylcoumarin As An Improved Fluorogenic Substrate For Deubiquitinating Enzymes
    作者:Li,Yi-Tong; Huang,Yi-Chao; Xu,Yang; Pan,Man; Li,Yi-Ming
    参考文献:Tetrahedron 日期:2016 卷标:72(27-28) 页码:4085-4090]

    343310-64-5 = 85157-21-7
    反应条件:1.1 Reagents: Sodium Hydroxide; Reflux1.2 Reagents: Sulfuric Acid; Ph 2
    标题:Dual-Reactable Fluorescent Probes For Highly Selective And Sensitive Detection Of Biological H2S
    作者:Wei,Chao; Wang,Runyu; Zhang,Changyu; Xu,Guoce; Li,Yanyan; Et Al
    参考文献:Chemistry - An Asian Journal 日期:2016 卷标:11(9) 页码:1376-1381
3-氨基苯酚置于硫酸,Sodium Hydroxide体系中,用 水,乙酸乙酯 作为反应溶剂,化学反应 13.0H,反应生成 7-氨基-4-羧甲基香豆素
参考文献:泛素7-氨基-4-氨基甲酰基甲基香豆素作为改良的去泛素化酶的荧光底物
标题:泛素7-氨基-4-氨基甲酰基甲基香豆素作为改良的去泛素化酶的荧光底物
摘要:开发了一种新的荧光底物ub-Acc(泛素c末端7-氨基-4-氨基甲酰基甲基-香豆素)用于dub(去泛素化酶)活性测定.与经典dub底物ub-Amc(泛素c末端7-氨基-4-甲基香豆素)相比,该底物的合成效率更高.使用uch-L3,Otud2和usp30的dub分析表明,Ub-Acc的灵敏度比ub-Amc高近2倍.
DOI:10.1016/j.Tet.2016.05.041

海关参考信息

专利信息


专利号:US-7629437-B2
优先权日:2000-06-02
标题 :Fluorogenic materials and uses thereof
发明人：HARRIS JENNIFER L; BACKES BRADLEY J; ELLMAN JONATHAN A; CRAIK CHARLES S
权利人:UNIV CALIFORNIA
摘要:A method is presented for the preparation and use of fluorogenic peptide substrates that allows for the configuration of general substrate libraries to rapidly identify the primary and extended specificity of enzymes, such as proteases. The substrates contain a fluorogenic-leaving group, such as 7-amino-4-carbamoylmethyl-coumarin (ACC). Substrates incorporating the ACC leaving group show comparable kinetic profiles as those with the traditionally used 7-amino-4-methyl-coumarin (AMC) leaving group. The bifunctional nature of ACC allows for the efficient production of single substrates and substrate libraries using solid-phase synthesis techniques.

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主要参考文献

参考标题:Bifunctional Coumarin Derivatives In Solution And Solid Phase Synthesis Of Fluorogenic Enzyme Substrates
作者:Christos Charitos,George Kokotos,Chryssa Tzougraki |发布日期:2001.1
摘要:Solid Phase Synthesis Of Fluorogenic Enzyme Substrates Was Examined. The Intramolecularly Quenched Fluorogenic Substrate N-(7-Amino-4-Coumarinyl-Acetyl)-L-Phenylalanyl-P-Nitroanilide 5, And The Fluorogenic One Ethyl 7-(Glutaryl-L-Phenylalanilamido)-4-Coumarinyl-Acetate 8, Both Suitable For Chymotrypsin And/or Chymotrypsin Like Enzymes Determination, Were Prepared In Solution. The Substrates 7-Oleylox

合成参考文献


参考文献:10.1007/s41061-024-00462-z
摘要:Gupta D, Guliani E, Bajaj K. Coumarin-Synthetic Methodologies, Pharmacology, and Application as Natural Fluorophore. Top Curr Chem (Cham). 2024 May 09;382(2):16. doi: 10.1007/s41061-024-00462-z.
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