CAS: 115-02-6; Azaserine

该化合物是一种合成化合物,被归类为抗生素和抗甲代谢物,主要以其在癌症研究中的作用和作为生化研究的工具而著称;是一种抑制酶-麦基胺胺转移酶的微米仿真剂,该酶对核糖酸合成至关重要,从而干扰DNA和RNA合成.这一机制使氨基氨在研究细胞过程和核糖酸耗竭的影响方面特别宝贵.该化合物一般是白到白的晶状固体,水和各种有机溶剂中可溶解.在实验室环境中,阿扎西林被用来探究其对细胞生长和分化的影响,特别是肿瘤细胞细胞的影响.然而,由于其强大的生物活动,必须谨慎处理,因为它能够表现出细胞毒性效应.其使用主要限于研究应用,并且不被批准用于人体的治疗用途.

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(S)-3-(2-Amino-acetoxy)-2-(2,2,2-trifluoro-acetylamino)-propionic acid (S)-3-(2-Benzyloxycarbonylamino-acetoxy)-2-(2,2,2-trifluoro-acetylamino)-propionic acid benzyl esterO-glycoloyl-L-serineO-glycoloyl-L-serine

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    📜(S)-3-(2-Aminoacetoxy)-2-(2,2,2-Trifluoroacetamido)Propanoic Acid 反应生成偶氮丝氨酸
    参考文献:New Synthesis Of Azaserine
    标题:New Synthesis Of Azaserine
    摘要:
    Doi:10.1021/jo00418A033

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    专利信息


    专利号:US-10925977-B2
    优先权日:2006-10-05
    标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
    发明人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
    权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
    摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

    专利号:US-2003159164-A1
    优先权日:1998-05-29
    标 题:Compositions and methods for the synthesis of fatty acids, their derivatives and downstream products
    发明人:KOPCHICK JOHN JOSEPH; KELDER BRUCE; HUANG YUNG-SHENG; KIRCHNER STEPHEN J; MUKERJI PRADIP
    摘要:The invention generally relates to synthesis of essential fatty acids and their derivatives, long-chain polyunsaturated fatty acids (LC-PUFAs) and eicosanoids in transfected cells and in transgenic animals.

    专利号:US-12391691-B2
    优先权日:2018-11-16
    标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
    发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
    权利人:AMGEN INC
    摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

    专利号:US-2025206736-A1
    优先权日:2019-11-14
    标题 :Synthesis of kras g12c inhibitor compound
    发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
    权利人:AMGEN INC
    摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

    专利号:WO-2017100796-A1
    优先权日:2015-12-11
    标 题 :Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
    发明人:WONG CHI-HUEY; HSU TSUI-LING; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI
    权利人:SINACA ACAD; WONG CHI-HUEY; HSU TSUI-LING
    摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta- 4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for disgnostic and therapeutic uses.

    专利号:US-2017283878-A1
    优先权日:2015-12-11
    标题:Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
    发明人:WONG CHI-HUEY; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI; HSU TSUI-LING
    权利人:ACADEMIA SINICA
    摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for diagnostic and therapeutic uses.

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    主要参考文献


    1: Protivinsky R. Azaserine. Antibiot Chemother (1971). 1971;17:95-100. doi: 10.1159/000392366.
    10:73-7. 63(6):1033-8. 34(6):1518-1529. doi: 10.1021/acs.chemrestox.0c00471. Epub 2021 Jun 1. 4(7):775-91. 129(2):153-64. doi: 10.1016/0027-5107(84)90148-9. 10(5):889-901. doi: 10.1002/1097-0142(195709/10)10:5<889::aid-cncr2820100506>3.0.co;2-t. 71(4):485-91.
    9: Wei ZW, Niikura H, Wang M, Ryan KS. Identification of the Azaserine Biosynthetic Gene Cluster Implicates Hydrazine as an Intermediate to the Diazo Moiety. Org Lett. 2023 Jun 9;25(22):4061-4065. doi: 10.1021/acs.orglett.3c01229. Epub 2023 May 26. 173(4393):72. doi: 10.1038/173072a0.

    合成参考文献


    摘要:CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980, 4(1)(432), 1980
    摘要:Journal of Pharmacy and Pharmacology., 18(760), 1966 []
    摘要:Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 144
    摘要:Jaber HM et al; Data Acquisition for Environmental transport and Fate Screening for Compounds of Interest to the Office of Emergency and Remedial Response USEPA-600/6-84-011 (NTIS PB84-245281) pp. 156 (1984)
    摘要:GENE-TOX Program: Current Status of Bioassay in Genetic Toxicology. U.S. Environmental Protection Agency, Washington, DC. Office of Toxic Substances and Pesticides. (For program information, contact Environmental Mutagen Information Center, Oak Ridge National Laboratory, Post Office Box Y, Oak Ridge, Tennessee 37830. Telephone (615) 574-7871)
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