CAS: 1404-64-4; (E)-N-((2S)-1-Hydroxy-3-(((Methylthio)Methyl)Sulfinyl)Propan-2-yl)-3-(6-Methyl-2,4-Dioxo-1,2,3,4-Tetrahydropyrimidin-5-yl)Acrylamide

该化合物是一种抗生素化合物,主要以其作为蛋白质合成抑制剂的作用而闻名,主要来自细菌链球菌,并展示了一种独特的行动机制,与核子核糖核酸结合,从而干扰细菌细胞的转化过程.该化合物的特征是其个性,其"(+)"称号表明其特定的光学活动.对分泌素进行了研究,以研究其潜在的治疗用途,特别是治疗某些类型的癌症和细菌感染,尽管其临床用途因毒性问题而受到限制.该物质通常以固态的形式出现,在各种有机溶剂中溶解.其化学结构具有环形和功能组的复杂安排,有助于其生物活动.

结构式图片

上下游产品

3-(2,4-二氧代-6-甲基-5-嘧啶基)丙烯酸 (E)-β-(2,4-Dioxo-6-Methyl-1,2,3,4-Tetrahydropyrimidin-5-yl)Acrylic Acid 28277-67-0
Ethyl (E)-3-(2,4-Dioxo-6-Methyl-5-Pyrimidinyl)Acrylate 28277-68-1

合成工艺路线路线简述

    📜6-甲基-2,4-二氧代-1,2,3,4-四氢-嘧啶-5-甲醛置于n-羟基-7-氮杂苯并三氮唑,四丁基氟化铵,N,N'-二环己基碳二亚胺,Sodium Hydroxide体系中,用 四氢呋喃,1,4-二氧六环,甲醇,水,N,N-二甲基甲酰胺 用作溶剂,化学反应 17.0H,反应生成司帕索霉素
    参考文献:通过硫酸盐阴离子介导的迭代 C-S 键形成全合成 Sparsomycin 和 Sparoxomycins A1 和 A2
    标题:通过硫酸盐阴离子介导的迭代 C-S 键形成全合成 Sparsomycin 和 Sparoxomycins A1 和 A2
    摘要:嘧啶基丙烯酰胺抗生素sparsomycin和sparoxomycins A 1和a 2已实现全合成.稀疏霉素的合成依赖于磺酸根阴离子对卤代烷的反复亲核攻击,构建具有高非对映选择性的二硫缩醛一氧化碳链.随后,通过试剂控制的非对映选择性氧化稀疏霉素的末端硫醚部分,直接得到稀疏霉素a 1和a 2 .
    Doi:10.1021/acs.Orglett.3C03791

    海关参考信息

    专利信息


    专利号:US-2004126792-A1
    优先权日:2002-09-18
    标 题 :Synthesis and applications of trinucleotide pCpCpA-3'-NH-aminoacyl derivatives
    发明人:ZHANG BILIANG
    摘要:The present invention relates to the synthesis of novel compounds for the inhibition of peptide synthesis in the ribosome. It also relates to improved methods for directly monitoring peptide bond formation in the ribosome. These compounds can be used for high throughput screening of proposed therapeutically active drug species (e.g., antibiotics) targeted to ribosomes.

    专利号:US-9982005-B2
    优先权日:2013-04-04
    标 题 :Macrolides and methods of their preparation and use
    发明人:MYERS ANDREW G; SEIPLE IAN BASS; ZHANG ZIYANG
    权利人:HARVARD COLLEGE
    摘要:Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.

    专利号:US-11466046-B2
    优先权日:2014-10-08
    标题 :14-membered ketolides and methods of their preparation and use
    发明人:MYERS ANDREW G; SEIPLE IAN BASS; ZHANG ZIYANG
    权利人:HARVARD COLLEGE
    摘要:Provided herein are methods of preparing new 14-membered ketolides via coupling of an eastern and western half moiety, followed by macrocyclization, and optional functionalization. Intermediates in the synthesis of these ketolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using these ketolides are also provided.

    专利号:US-8734846-B2
    优先权日:2008-06-16
    标 题 :Methods for the preparation of targeting agent functionalized diblock copolymers for use in fabrication of therapeutic targeted nanoparticles
    发明人:ALI MIR M; HRKACH JEFF; ZALE STEPHEN E; ALVAREZ DE CIENFUEGOS LUIS
    权利人:BIND BIOSCIENCES INC
    摘要:This application provides nanoparticles and methods of making nanoparticles using pre-functionalized poly(ethylene glycol)(also referred to as PEG) as a macroinitiator for the synthesis of diblock copolymers. Ring opening polymerization yields the desired poly(ester)-poly (ethylene glycol)-targeting agent polymer that is used to impart targeting capability to therapeutic nanoparticles. This “polymerization fromâ€? approach typically employs precursors of the targeting agent wherein the reactivity of functional groups of the targeting agent is masked using protecting groups. Also described is a “coupling toâ€? that utilized the poly(ethylene glycol)-targeting agent conjugate where the targeting agent remains in its native un-protected form. This method uses “orthogonalâ€? chemistry that exhibit no cross reactivity towards functional groups typically found within targeting agents of interest.

    专利号:US-2013035307-A1
    优先权日:2010-01-26
    标 题:Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers
    发明人:PRESTWICH GLENN D; KENNEDY THOMAS P
    权利人:UNIV UTAH RES FOUND; PRESTWICH GLENN D; KENNEDY THOMAS P
    摘要:Described herein are methods for the treatment and prevention of tumor metastasis using alkylated and fluoroalkylated semi-synthetic glycosaminoglycan ethers (“SAGEsâ€?). The synthesis of sulfated alkylated and fluoroalkylated SAGEs is also described.

    专利号:US-2008214827-A1
    优先权日:2004-02-03
    标 题:Synthesis of Cyanoimino-Benzoimidazoles
    发明人:GOEHRING R RICHARD; WHITEHEAD JOHN; SHAO BIN
    权利人:EURO CELTIQUE SA
    摘要:Disclosed in certain embodiments is a process for synthesizing a compound of formula (V) and salts thereof.

    供应商参考报价(招募中)

    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: Miyauchi K, Komano J, Myint L, Futahashi Y, Urano E, Matsuda Z, Chiba T, Miura H, Sugiura W, Yamamoto N. Rapid propagation of low-fitness drug-resistant mutants of human immunodeficiency virus type 1 by a streptococcal metabolite sparsomycin. Antivir Chem Chemother. 2006;17(4):167-74. doi: 10.1021/jp100579y. doi: 10.1002/cbic.201100508. Epub 2011 Oct 28. doi: 10.1002/jmr.996. Review. doi: 10.1261/rna.035964.112. Epub 2012 Dec 17.
    10: Lazaro E, San Felix A, van den Broek LA, Ottenheijm HC, Ballesta JP. Interaction of the antibiotic sparsomycin with the ribosome. Antimicrob Agents Chemother. 1991 Jan;35(1):10-3.
    11: Hofs HP, Wagener DJ, De Vos D, Ottenheijm HC, Winkens HJ, Bovee PH, De Grip WJ. Antitumour activity and retinotoxicity of ethyldeshydroxy-sparsomycin in mice. Eur J Cancer. 1995;31A(9):1526-30.

    合成参考文献


    摘要:Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory., 2(6)(-), 1971
    参考文献:10.1261/rna.035964.112
    摘要:Ermolenko DN, Cornish PV, Ha T, Noller HF. Antibiotics that bind to the A site of the large ribosomal subunit can induce mRNA translocation. RNA. 2013 Feb;19(2):158–66.
    参考文献:10.1128/jvi.56.3.683-690.1985
    摘要:Petersen RB, Hackett PB. Characterization of ribosome binding on Rous sarcoma virus RNA in vitro. J Virol. 1985 Dec;56(3):683–90. doi: 10.1128/jvi.56.3.683-690.1985.
    参考文献:10.1128/jb.179.4.1385-1392.1997
    摘要:Parry RJ, Hoyt JC. Purification and preliminary characterization of (E)-3-(2,4-dioxo-6-methyl-5-pyrimidinyl)acrylic acid synthase, an enzyme involved in biosynthesis of the antitumor agent sparsomycin. J Bacteriol. 1997 Feb;179(4):1385–92. doi: 10.1128/jb.179.4.1385-1392.1997.
    📝 需求与反馈
    尽可能描述清楚需求与问题信息
    ×

    通知