CAS: 38136-70-8; (3S,8As)-3-((1H-Indol-3-yl)Methyl)Hexahydropyrrolo[1,2-A]Pyrazine-1,4-Dione

该化合物是一种主要由和Aspergilus物种生产的真菌代谢物产生的生物活性藻类,具有明显的结构复杂性,其特点是一个含有前不久的无花果味的二氯硝基苯核心体,由于其潜在的生物活动,包括抗微生物和细胞毒性特性,引起了人们的兴趣,使其成为药理研究的候选体.它独特的脚架也作为合成和药用化学研究的宝贵模板.Brevianamod F在标准实验室条件下具有很高的纯度和稳定性,确保了实验应用的可靠性.研究人员认为它对于探索二级代谢物生物合成和药物发现途径的作用很有价值.

结构式图片

上下游产品

N-(tert-butoxycarbonyl)-D-proline L-tryptophan methyl ester 1-(tert-butoxycarbonyl)-L-proline (S)-tryptophan methyl ester hydr°Chloride(3S,8aR)-3-((2-(4-(trifluoromethyl)phenyl)-1H-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione deoxybrevianamide E 24H20BrF3N4O3C24H20BrF3N4O3 22H21BrN4O2C22H21BrN4O2

合成工艺路线路线简述

    📜N-苄氧羰基-L-色氨酸置于5%-Palladium/activated Carbon,氢气,盐酸-N-乙基-N'-(3-二甲氨基丙基)碳二亚胺体系中,用 甲醇,二氯甲烷 用作溶剂,20.0 °C,506.66 Kpa 条件下,反应 26.0H,反应生成(3S,8As)-3-(1H-吲哚-3-基甲基)-2,3,6,7,8,8A-六氢吡咯并[2,1-F]吡嗪-1,4-二酮
    参考文献:Beyond The Diketopiperazine Family With Alternatively Bridged Brevianamide F Analogues
    标题:Beyond The Diketopiperazine Family With Alternatively Bridged Brevianamide F Analogues
    摘要:A Method For The Preparation Of 3,5-Bridged Piperazin-2-Ones From A Tryptophan Proline-Based Diketopiperazine Is Described Using Diphosgene To Induce The Ring Closure. Density Functional Theory Calculations Were Conducted To Study The Mechanism Of This C-C Bond Formation. Several Derivatives Of The Thus Obtained Alpha-Chloroamine Were Synthesized By Substitution Of The Chlorine Atom Using A Range Of O-,N-,S-,And C-Nucleophiles. This Novel Class Of Brevianamide F Analogues Possess Interesting Breast Cancer Resistance Protein Inhibitory Activity.
    Doi:10.1021/acs.Joc.5B01161

    海关参考信息

    专利信息


    专利号:US-7723082-B2
    优先权日:2002-06-21
    标题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives
    发明人:GONDRY MURIEL; GENET ROGER; LAUTRU SYLVIE; PERNODET JEAN-LUC
    权利人:COMMISSARIAT ENERGIE ATOMIQUE; CENTRE NAT RECH SCIENT
    摘要:The invention concerns novel isolated natural or synthetic polynucleotides and polypeptides coded by said polynucleotides, involved in the synthesis of diketopiperazine derivatives, vectors comprising said polynucleotides, micro-organisms transformed with said polynucleotides, uses of said polynucleotides and said polypeptides, as well as methods for the synthesis of diketopiperazine derivatives, including cyclodipeptides and diketopiperazine derivatives 3- and 6-substituted by α,β-unsaturated amino acid side chains.

    专利号:US-2006051837-A1
    优先权日:2002-06-21
    标 题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:US-2007048817-A1
    优先权日:2002-06-21
    标 题:Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:AU-2003255681-B2
    优先权日:2002-06-21
    标题:Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:AU-2003255681-A1
    优先权日:2002-06-21
    标题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

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    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Wauters I, Goossens H, Delbeke E, Muylaert K, Roman BI, Van Hecke K, Van Speybroeck V, Stevens CV. Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues. J Org Chem. 2015 Aug 21;80(16):8046-54. doi: 10.1021/acs.joc.5b01161. Epub 2015 Aug 3. doi: 10.1007/s00253-012-4130-0. Epub 2012 Jun 3.

    合成参考文献


    参考文献:10.1002/cbic.200600003
    摘要:Maiya S, Grundmann A, Li SM, Turner G. The fumitremorgin gene cluster of Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase. Chembiochem. 2006 Jul;7(7):1062–9. doi: 10.1002/cbic.200600003.
    参考文献:10.1021/jacs.0c06312
    摘要:Shende VV, Khatri Y, Newmister SA, Sanders JN, Lindovska P, Yu F, Doyon TJ, Kim J, Houk KN, Movassaghi M, Sherman DH. Structure and Function of NzeB, a Versatile C-C and C-N Bond-Forming Diketopiperazine Dimerase. J Am Chem Soc. 2020 Oct 14;142(41):17413–24.
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