CAS: 57-62-5; Chlortetracycline

该化合物是四环菌类的广谱抗生素,主要用于治疗人类和动物的细菌感染,其特点是黄色晶状晶状,在水中可溶解,便于各种配方使用,氯四环环烷的化学结构包括一个含有多种羟基和二甲基氨基的环烷核心,通过抑制细菌中的蛋白合成,促进其抗菌活动;其行动机制涉及与30S的血清亚元素结合,防止氨基-氨基甲酸的附加,从而破坏翻译过程;氯环环环对多种克丁和克丁涅丁基细菌以及某些原生虫有效,但由于抗生体抗药性出现,以及新抗生菌的可用性得到提高,因此其使用量减少;此外,必须指出,氯三环烷可产生副效应,包括胃肠扰和光敏化作用,从而影响转化过程.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

methanol 4-epi chlortetracyclineis°Chlortetracycline S)-4-((1S)-4-carbamoyl-2t-dimethylamino-3,6ξ-dihydroxy-5-oxo-cyclohex3-en-r-yl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid(S)-4-((1S)-4-carbamoyl-2t-dimethylamino-3,6ξ-dihydroxy-5-oxo-cyclohex3-en-r-yl)-3-((S)-7-chloro-4-hydroxy-1-methyl-3-oxo-phthalan-1-yl)-butyric acid 4-methoxyphthalic acid TETRACYCLINE

合成工艺路线路线简述

    甲醇,(4S,6S,12Ar)-7-Chloro-4-(Dimethylamino)-1,6,10,11,12A-Pentahydroxy-6-Methyl-3,12-Dioxo-4,4A,5,5A-Tetrahydrotetracene-2-Carboxamide,Alkaline Earth Salt Of/the/ Methylsulfuric Acid 反应生成 金霉素
    参考文献:Studies Of The Reversible Epimerization occurring In The Tetracycline Family. The Preparation,Properties And Proof Of Structure Of Some 4-Epi-Tetracyclines
    标题:Studies Of The Reversible Epimerization occurring In The Tetracycline Family. The Preparation,Properties And Proof Of Structure Of Some 4-Epi-Tetracyclines
    摘要:
    DOI:10.1021/ja01568A050

    海关参考信息

    专利信息


    专利号:WO-2012047907-A9
    优先权日:2010-10-04
    标题 :Synthesis of c5-substituted tetracyclines, uses thereof, and intermediates thereto
    发明人:MYERS ANDREW G; WRIGHT PETER M; HECKER EVAN
    权利人:HARVARD COLLEGE; MYERS ANDREW G; WRIGHT PETER M; HECKER EVAN
    摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides more efficient routes for preparing the enone intermediate and allows for a wide variety of substituents at position 5 of the tetracycline ring system.

    专利号:WO-2024182268-A1
    优先权日:2023-02-27
    标 题 :Liquid phase peptide support synthesis of peptides and peptidomimetics
    发明人:HAN AMY
    权利人:REGENERON PHARMA
    摘要:The present invention provides compounds useful as support for liquid phase organic synthesis e.g., liquid phase organic synthesis of peptides and peptidomimetics. In one aspect, the present invention provides a compound having a structure of Formula (I) where R1, R2, R3, m, and n are as described herein and methods of making and using same.

    专利号:US-9688644-B2
    优先权日:2009-04-30
    标 题 :Synthesis of Tetracyclines and intermediates thereto
    发明人:MYERS ANDREW G; KUMMER DAVID A; LI DERUN; HECKER EVAN; DION AMELIE; WRIGHT PETER M
    权利人:HARVARD COLLEGE
    摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides more efficient routes for preparing the enone intermediate and allows for substituents at positions 4a, 5, 5a, and 12a of the tetracycline ring system.

    专利号:US-9884830-B2
    优先权日:2004-05-21
    标题 :Synthesis of tetracyclines and analogues thereof
    发明人:MYERS ANDREW G; CHAREST MARK G; LERNER CHRISTIAN D; BRUBAKER JASON D; SIEGEL DIONICIO R
    权利人:HARVARD COLLEGE
    摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.

    专利号:US-8907104-B2
    优先权日:2006-10-11
    标 题 :Synthesis of enone intermediate
    发明人:MYERS ANDREW G; BRUBAKER JASON D
    权利人:HARVARD COLLEGE
    摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides a more efficient route for preparing the enone intermediate.

    专利号:US-8486921-B2
    优先权日:2006-04-07
    标 题:Synthesis of tetracyclines and analogues thereof
    发明人:MYERS ANDREW G; BRUBAKER JASON D; SUN CUIXIANG; WANG QIU
    权利人:MYERS ANDREW G; BRUBAKER JASON D; SUN CUIXIANG; WANG QIU; HARVARD COLLEGE
    摘要:The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetra-cycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-pro liferative agents in the treatment of diseases of humans or other animals.
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    主要参考文献


    1: Chen Z, Wang Y, Wen Q. Effects of chlortetracycline on the fate of multi-antibiotic resistance genes and the microbial community during swine manure composting. Environ Pollut. 2018 Jun;237:977-987. doi: 10.1016/j.envpol.2017.11.009. Epub 2017 Nov 11.

    合成参考文献


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    摘要:Antibiotiki., 20(793), 1975
    摘要:Journal of Agricultural and Food Chemistry., 17(497), 1969
    摘要:S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
    摘要:https://www.sciencedirect.com/science/article/abs/pii/S0003267018311693
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