CAS: 82-89-3; 4-Methoxy-5-((5-Methyl-4-Pentyl-2H-Pyrrol-2-Ylidene)Methyl)-1H,1'H-2,2'-Bipyrrole

该化合物是某些细菌物种,特别是Serratia marcescens 所生的自然产生的红色色素,这种三叶红色化合物具有显著的生物活动,包括抗微生物,抗癌和免疫抑制特性.它的独特结构使得它能够与细胞膜和细胞内目标相互作用,使其成为生物医学研究的一个主题.Prodigiosin在保留正常细胞的同时诱发癌症细胞的流行性病的能力凸显了它作为治疗剂的潜力.此外,它在不同的pH条件下的稳定性和有机溶剂的溶解性促进了它在实验应用中的使用.研究继续探索其在药物发展和生物技术方面的行动机制及潜在应用.

结构式图片

物理性质

MSDS等安全信息

合成工艺路线路线简述

  • 10476-41-2 + 18320-91-7 = 82-89-3
    反应条件:1.1 Solvents: Methanol1.2 Catalysts: Hydrochloric Acid
    标题:Total Synthesis Of Prodigiosin,Prodigiosene,And Desmethoxyprodigiosin: Diels-Alder Reactions Of Heterocyclic Azadienes And Development Of An Effective Palladium(Ii)-Promoted 2,2'-Bipyrrole Coupling Procedure
    作者:Boger,Dale L.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(7) 页码:1405-15]

    10476-41-2 + 18320-91-7 = 82-89-3
    反应条件:1.1 Catalysts: Hydrochloric Acid Solvents: Methanol
    标题:Total Synthesis Of Prodigiosin
    作者:Boger,Dale L.; Et Al
    参考文献:Tetrahedron Letters 日期:1987 卷标:28(22) 页码:2499-502]

    50-99-7 + 56-81-5 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    57-50-1 + 56-81-5 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    9005-25-8 = 82-89-3
    反应条件:1.1 Reagents: Sulfuric Acid Magnesium Salt (1:1),Ferrous Sulfate,Manganese Sulfate,Calcium Chloride Solvents: Water
    标题:Enhancing Production Of Prodigiosin From Serratia Marcescens C3 By Statistical Experimental Design And Porous Carrier Addition Strategy
    作者:Chen,Wei-Chuan; Et Al
    参考文献:Biochemical Engineering Journal 日期:2013 卷标:78 页码:93-100]

    112373-38-3 = 82-89-3
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: Ethylene Glycol2.1 Solvents: Methanol2.2 Catalysts: Hydrochloric Acid
    标题:Total Synthesis Of Prodigiosin,Prodigiosene,And Desmethoxyprodigiosin: Diels-Alder Reactions Of Heterocyclic Azadienes And Development Of An Effective Palladium(Ii)-Promoted 2,2'-Bipyrrole Coupling Procedure
    作者:Boger,Dale L.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(7) 页码:1405-15]

    112373-38-3 = 82-89-3
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: Ethylene Glycol2.1 Catalysts: Hydrochloric Acid Solvents: Methanol
    标题:Total Synthesis Of Prodigiosin
    作者:Boger,Dale L.; Et Al
    参考文献:Tetrahedron Letters 日期:1987 卷标:28(22) 页码:2499-502]

    57-48-7 + 56-81-5 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    56-81-5 + 63-42-3 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    56-81-5 + 69-65-8 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    69-79-4 + 56-81-5 = 82-89-3
    反应条件:1.1 Reagents: Sodium Chloride Solvents: Water; 48 H,Ph 7.0,25 °C
    标题:Assessment Of Process Parameters Influencing The Enhanced Production Of Prodigiosin From Serratia Marcescens And Evaluation Of Its Antimicrobial,Antioxidant And Dyeing Potentials
    作者:Gulani,Chandni; Et Al
    参考文献:Malaysian Journal Of Microbiology 日期:2012 卷标:8(2) 页码:116-122]

    1213263-03-6 = 82-89-3
    反应条件:1.1 Reagents: 2,2,2-Trifluoroethanol; 10 Min,90 - 120 °C2.1 Reagents: Atp Disodium Solvents: Dimethyl Sulfoxide,Water; 4 H,Ph 7,30 °C
    标题:Condensing Enzymes From Pseudoalteromonadaceae For Prodiginine Synthesis
    作者:Brass,Hannah U. C.; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2019 卷标:361(11) 页码:2659-2667]

    = 82-89-3
    反应条件:1.1 Reagents: Hydrazine1.2 Reagents: Tosyl Chloride1.3 Reagents: Sodium Carbonate Solvents: Diethylene Glycol2.1 Reagents: Hydrochloric Acid Solvents: Water
    标题:Pyrrole-Singlet Oxygen Reactions Leading To α,α'-Bipyrroles. Synthesis Of Prodigiosin And Analogs
    作者:Wasserman,Harry H.; Et Al
    参考文献:Tetrahedron Letters 日期:1999 卷标:40(43) 页码:7587-7589]

    7207-49-0 = 82-89-3
    反应条件:1.1 -2.1 Reagents: Atp Disodium Solvents: Dimethyl Sulfoxide,Water; 4 H,Ph 7,30 °C
    标题:Condensing Enzymes From Pseudoalteromonadaceae For Prodiginine Synthesis
    作者:Brass,Hannah U. C.; Et Al
    参考文献:Advanced Synthesis & Catalysis 日期:2019 卷标:361(11) 页码:2659-2667]

    91567-33-8 = 82-89-3
    反应条件:1.1 Reagents: Hydrazine1.2 Reagents: Tosyl Chloride Solvents: Pyridine1.3 Reagents: Sodium Carbonate Solvents: Ethylene Glycol2.1 Catalysts: Hydrogen Bromide
    标题:The Chemistry Of Vicinal Tricarbonyls. A Total Synthesis Of Prodigiosin
    作者:Wasserman,Harry H.; Et Al
    参考文献:Tetrahedron Letters 日期:1989 卷标:30(13) 页码:1725-8]

    92198-32-8 = 82-89-3
    反应条件:1.1 Reagents: Lithium Hydroxide Solvents: Methanol,Tetrahydrofuran,Water1.2 Reagents: Sodium Bicarbonate,Iodine,Sodium Iodide Solvents: 1,2-Dichloroethane,Water1.3 Reagents: Potassium Carbonate,Hydrogen Catalysts: Palladium Solvents: Methanol1.4 Reagents: Hydrazine1.5 Reagents: Potassium Hydroxide Solvents: Ethylene Glycol2.1 Solvents: Methanol2.2 Catalysts: Hydrochloric Acid
    标题:Total Synthesis Of Prodigiosin,Prodigiosene,And Desmethoxyprodigiosin: Diels-Alder Reactions Of Heterocyclic Azadienes And Development Of An Effective Palladium(Ii)-Promoted 2,2'-Bipyrrole Coupling Procedure
    作者:Boger,Dale L.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(7) 页码:1405-15

海关参考信息

专利信息


专利号:RU-2145957-C1
优先权日:1993-12-23
标 题:Derivatives of 5-[(2h-pyrrole-2-ylidene)methyl]-2,2'-bi-1h- -pyrrole showing immunomodulating activity, method of their synthesis, pharmaceutical composition based on thereof

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主要参考文献


1: Eluu SC, Obayemi JD, Yiporo D, Salifu AA, Oko AO, Onwudiwe K, Aina T, Oparah JC, Ezeala CC, Etinosa PO, Osafo SA, Ugwu MC, Esimone CO, Soboyejo WO. Luteinizing Hormone-Releasing Hormone (LHRH)-Conjugated Cancer Drug Delivery from Magnetite Nanoparticle-Modified Microporous Poly-Di-Methyl-Siloxane (PDMS) Systems for the Targeted Treatment of Triple Negative Breast Cancer Cells. J Funct Biomater. 2024 Jul 28;15(8):209. doi: 10.3390/jfb15080209. 23(1):234. doi: 10.1186/s12934-024-02510-1.
3: Zheng Q, Zhang W, Wang L, Wen X, Wu J, Ren Y, Fu R. Functional dyeing of cellulose macromolecule/synthetic fibers two-component fabrics with sustainable microbial prodigiosins. Int J Biol Macromol. 2024 Aug 22;278(Pt 3):134964. doi: 10.1016/j.ijbiomac.2024.134964. Epub ahead of print. 25(15):8395. doi: 10.3390/ijms25158395.
5: Esteves NC, Scharf BE. Serratia marcescens ATCC 274 increases production of the red pigment prodigiosin in response to Chi phage infection. Sci Rep. 2024 Jul 31;14(1):17750. doi: 10.1038/s41598-024-68747-3.

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