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
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.