CAS: 21200-24-8; Indolmycin

该化合物是一种自然形成的抗生素,属于非球衍生物类别,主要以其抗菌特性而闻名,特别是针对抗乳性细菌的抗菌性能;该化合物展示了一种独特的行动机制,它抑制了对氨基酸性锥体生物合成至关重要的锥体酶;这种抑制干扰干扰了易感染细菌的蛋白合成和细胞代谢;该物质的特点在于其复杂的分子结构,其中包括一个无花环,有助于其生物活动;它通常与微生物来源,特别是某些血管菌株隔离;除了其抗菌效应外,研究还表明,由于它能够干扰细胞过程,癌症治疗可能应用.然而,其临床用途有限,必须进一步研究,以充分了解其药理特性和潜在治疗用途.正如许多抗生素一样,抗药性可以发展,需要仔细研究其使用.

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    上下游产品

    吲哚霉素 Indolmycin 21193-77-1
    (5S)-2-Amino-5-[(1R)-1-(1H-Indol-3-yl)Ethyl]-2-Oxazolin-4-One 20906-48-3
    2-Amino-5-[1-(1H-Indol-3-yl)Ethyl]-2-Oxazolin-4-One 20906-46-1
    Ethyl (2S,3R)-2-Hydroxy-3-(3-Indolyl)Butanoate 150131-72-9
    (2S,3R)-2-Hydroxy-3-(1H-Indol-3-yl)Butanoic Acid 26622-60-6
    Methyl (2S,3R)-3-(1H-Indol-3-yl)-2-Hydroxybutanoate 61521-54-8
    2-Hydroxy-3-Indol-3-Yl-Butyric Acid Methyl Ester 5192-19-8

    合成工艺路线路线简述

      📜Methyl (2S,3R)-3-(1H-Indol-3-yl)-2-Hydroxybutanoate置于四氢呋喃,Lithium Hydroxide,3-Ethyl-2-Chlorobenzoxazolium Tetrafluoroborate,水,对甲苯磺酸,溶剂黄146,三乙胺体系中,用 四氢呋喃,1,4-二氧六环,乙醚,水,乙腈 用作溶剂,化学反应 110.0H,反应生成(-)-吲哚霉素
      参考文献:吲哚霉素的不对称全合成
      标题:吲哚霉素的不对称全合成
      摘要:吲哚霉素的不对称全合成是通过关键中间体 α-吲哚霉素酸酯实现的.该酯是通过使用 (2R,3S)-3,4-二甲基-2-苯基全氢-1,4-氧氮杂-5 不对称合成制备的 (S)-3-(3-吲哚基) 丁酸甲酯氧化获得的,7-二酮.(2S,3R)-N-[2-Hydroxy-3-(3-Indolyl)-Butanoyl]-N'-Methylthiourea 由 α-Indolmycenicate 制备,用 2-Chlorobenzoxazolium 盐处理得到光学纯度为 93% 的吲哚霉素.
      Doi:10.1246/cl.1980.163

      海关参考信息

      专利信息


      专利号:US-2025042888-A1
      优先权日:2021-11-26
      标题 :A process for the preparation of indolmycin and derivatives thereof
      发明人:GULAM DASTAGER SYED; SHYAM SAID MADHUKAR; KHAN ABUJANAID; ARVIND KULKARNI AMOL
      权利人:COUNCIL OF SCIENT AND INDUSTRIAL RESEARCH AN INDIAN REGISTERED BODY INCORPORATED UNDER THE REGN
      摘要:The present disclosure relates to a new, simple, two step synthesis of Indolmycin and its derivatives of formula (I), in 4-5 hours. Formula (I) wherein said process comprising the step of: 10 (a) reacting indole derivative with methyl magnesium bromide in a suitable solvent at a temperature in the range of 0-30° C. followed by adding ethyl epoxy butanone in a suitable solvent at −20° C. for a period of 1-2 hrs and maintaining the obtained reaction mixture for 1 hr at −20° C. to obtain a compound; and (b) passing the compound obtained at step a), base and N-methylated quinidine 15 through solid-solid continuous flow reactor for 1 minute to obtain the compound of formula (I).

      专利号:US-3901899-A
      优先权日:1973-04-27
      标题 :Synthesis of indoles from anilines and intermediates therein
      发明人:GASSMAN PAUL G
      权利人:UNIV OHIO STATE RES FOUND
      摘要:Preparing indoles and intermediates therefor by reacting an Nhaloaniline with a Beta -carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the Beta carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an Alpha -ethyl- Beta -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like.

      专利号:US-3992392-A
      优先权日:1973-04-27
      标题:Synthesis of indoles from anilines and intermediates therein
      发明人:GASSMAN PAUL G
      权利人:UNIV OHIO STATE RES FOUND
      摘要:Preparing indoles and intermediates therefor by reacting an N-haloaniline with a β-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the β-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an α-ethyl-β -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures. The thio-ether-indole and thio-ether indolenine derivatives are useful as intermediates to make the indoles without the thio-ether group. The indoles are known compounds having a wide variety of uses, e.g., in making perfumes, dyes, amino acids, pharmaceuticals, agricultural chemicals and the like.

      专利号:WO-2012014109-A1
      优先权日:2010-07-30
      标题:Heterocyclic sulfonamides as inhibitors of transfer rna synthetase for use as antibacterial agents
      发明人:DAS BISWAJIT; UPADHYAY DILIP J; PURNAPATRE KEDAR; GHOSH SOMA; KATOCH RITA
      权利人:RANBAXY LAB LTD; DAS BISWAJIT; UPADHYAY DILIP J; PURNAPATRE KEDAR; GHOSH SOMA; KATOCH RITA
      摘要:The present invention provides aromatic sulphonamides as tRNA synthetase inhibitors and process for their synthesis, pharmaceutical composition and method for treatment. Compounds disclosed can be used as antibacterial agents for the treatment or prevention of conditions caused by or contributed by aerobic and anaerobic Gram-positive pathogens, more particularly against bacterium, for example Staphylococcus, Enterococci and Streptococci . Compounds disclosed are used in particular for the treatment of skin and soft tissue infection, Formula (I).

      专利号:CA-1043337-A
      优先权日:1973-04-27
      标题 :Synthesis of indoles from anilines and intermediates therein

      专利号:CN-109867643-A
      优先权日:2017-12-01
      标题:A kind of polysubstituted furan derivative and its synthesis

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      主要参考文献


      1: Williams TL, Yin YW, Carter CW Jr. Selective Inhibition of Bacterial Tryptophanyl-tRNA Synthetases by Indolmycin Is Mechanism-based. J Biol Chem. 2016 Jan 1;291(1):255-65. doi: 10.1074/jbc.M115.690321. Epub 2015 Nov 9.
      2: Du YL, Alkhalaf LM, Ryan KS. In vitro reconstitution of indolmycin biosynthesis reveals the molecular basis of oxazolinone assembly. Proc Natl Acad Sci U S A. 2015 Mar 3;112(9):2717-22. doi: 10.1073/pnas.1419964112. Epub 2015 Feb 17.
      3: Hurdle JG, O'Neill AJ, Chopra I. Anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections. J Antimicrob Chemother. 2004 Aug;54(2):549-52. Epub 2004 Jul 8. Epub 2002 Apr 22. doi: 10.1128/AAC.00723-09. Epub 2009 Jun 22.

      合成参考文献


      摘要:CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980, 5(127), 1981
      参考文献:10.1074/jbc.m202639200
      摘要:Kitabatake M, Ali K, Demain A, Sakamoto K, Yokoyama S, Söll D. Indolmycin Resistance of Streptomyces coelicolor A3(2) by Induced Expression of One of Its Two Tryptophanyl-tRNA Synthetases. Journal of Biological Chemistry. 2002 Jun;277(26):23882–7. doi: 10.1074/jbc.m202639200.
      参考文献:10.7164/antibiotics.57.345
      摘要:Yang SW, Chian TM, Terracciano J, Loebenberg D, Chen G, Patel M, Gullo V, Pramanik B, Chu M. Structure elucidation of a new diketopiperazine Sch 725418 from Micromonospora sp. J Antibiot (Tokyo). 2004 May;57(5):345–7. doi: 10.7164/antibiotics.57.345.
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