CAS: 714272-27-2; (Z)-3-((Z)-Benzylidene)-6-((5-(Tert-Butyl)-1H-Imidazol-4-yl)Methylene)Piperazine-2,5-Dione

该化合物一个小分子,主要以其作为免疫性血液剂的作用及其在肿瘤学中的潜在应用而闻名,其作用是针对细胞内的微囊动态,这可能导致抑制肿瘤生长和增强免疫反应.Plinabulin因其减轻化学治疗诱发的肺炎的能力而受到调查,从而改善了癌症治疗的安全和效能.该化合物展示了一种独特的行动机制,将其与传统的乳房化剂区别开来,使它成为癌症研究的话题.此外, Plinabulin在临床前科和临床研究中表现出了希望,展示了一种有利的安全特征.其药理和生物利用率也是研究的关键领域,因为它们影响着其治疗潜力.总的来说, Plinabulin代表了癌症治疗的一种新颖方法,将免疫性与直接抗舌效应相结合,并继续在临床环境中对其各种癌症类型的效力和安全性进行评估.

结构式图片

上下游产品

1-acetyl-3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-2,5-piperazinedione benzaldehyde 4-tert-butyl-1H-imidazole-5-carbaldehyde 1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione(S)-2-(4-(4-((((3Z,6Z)-6-benzylidene-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)-5-oxo-3,4,5,6-tetrahydropyrazin-2-yl)oxy)methoxy)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)-3-hydroxypropanoic acid sodium (S)-2-(4-(4-((((3Z,6Z)-6-benzylidene-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)-5-oxo-3,4,5,6-tetrahydropyrazin-2-yl)oxy)methoxy)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)-3-hydroxypropanoate (((3Z,6Z)-6-benzylidene-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)-5-oxo-3,4,5,6-tetrahydropyrazin-2-yl)oxy)methyl hex-5-ynoate

合成工艺路线路线简述

    📜Sodium (S)-2-(4-(4-((((3Z,6Z)-6-Benzylidene-3-((5-(Tert-Butyl)-1H-Imidazol-4-yl)Methylene)-5-Oxo-3,4,5,6-Tetrahydropyrazin-2-yl)Oxy)Methoxy)-4-Oxobutyl)-1H-1,2,3-Triazol-1-yl)Pentanedioate置于esterase Enzyme体系中,化学反应生成 (3Z,6Z)-3-[(5-叔丁基-1H-咪唑-4-基)亚甲基]-6-(苯亚甲基)-2,5-哌嗪二酮
    参考文献: Plinabulin Prodrug Analogs And Therapeutic Uses Thereof[fr] Analogues De Promédicaments à Base De Plinabuline Et Utilisations Thérapeutiques Associées
    标题: Plinabulin Prodrug Analogs And Therapeutic Uses Thereof[fr] Analogues De Promédicaments à Base De Plinabuline Et Utilisations Thérapeutiques Associées
    摘要:公开了式(i)和(i')的化合物,以及制备这些化合物的方法.还公开了用于治疗包括癌症和与血管增殖相关的非癌症疾病的组合物和方法.(式(i)和(i'))

    海关参考信息

    专利信息


    专利号:US-7935704-B2
    优先权日:2003-08-01
    标 题 :Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
    发明人:PALLADINO MICHAEL A; LLOYD GEORGE KENNETH; HAYASHI YOSHIO; NICHOLSON BENJAMIN
    权利人:NEREUS PHARMACEUTICALS INC
    摘要:Compounds represented by the following structure (I) are disclosed: n nas are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R 1 , R 1 ′, R 1 ″, R 2 , R 3 , R 4 , R 5 , and R 6 , X 1 and X 2 , Y, Z, Z 1 , Z 2 , Z 3 , and Z 4 may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating vascular proliferation are also disclosed.

    专利号:US-7956058-B2
    优先权日:2002-08-02
    标 题:Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof
    发明人:HAYASHI YOSHIO; PALLADINO JR MICHAEL A; GRODBERG JENNIFER
    权利人:NEREUS PHARMACEUTICALS INC
    摘要:Compounds represented by the following structure (I) are disclosed: n nas are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R 1 , R 1 ′, R 1 ′, R 2 , R 3 , R 4 , R 5 , and R 6 , X 1 and X 2 , Y, Z, Z 1 , Z 2 , Z 3 , and Z 4 may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating cancer and fungal infection are also disclosed.

    专利号:US-10434098-B2
    优先权日:2015-06-02
    标 题 :Deuterated dehydrophenylahistin compounds and preparation method thereof and use thereof in preparation of anti-tumor drugs
    发明人:LI WENBAO; SUN TIANWEN; WANG SHIXIAO; ZHAO JIANCHUN; CAI BING; GUAN HUASHI
    权利人:MARINE BIOMEDICAL RES INST QINGDAO CO LTD
    摘要:Provided are a deuterium-substituted dehydrophenylahistin-like compound, preparation method thereof and use in a preparation of antitumor drugs. The deuterium-substituted dehydrophenylahistin-like compound has a structure of general formula (I), and a synthesis method thereof comprises: firstly conducting a condensation reaction of diacetyldiketopiperazine and an aldehyde intermediate a or a deuterated aldehyde compound b to form a heterocyclic compound c or a deuterium-containing heterocyclic compound d, which is then subjected to a condensation reaction with benzaldehyde and a deuterium-substituted benzaldehyde-like compound to form the deuterium-substituted dehydrophenylahistin-like compound. Also provided are a highly effective deuterated aldehyde intermediate with a high deuterium substitution rate and a deuterium-containing heterocycle intermediate, and a synthesis method thereof. An experiment shows that the deuterium-substituted dehydrophenylahistin-like compound provided by the present invention has an effect on tubulin depolymerization and can treat a refractory solid tumor or lymphoma. The present invention provides a method for researching and developing antitumor drugs of the related compound.

    专利号:US-2005197344-A1
    优先权日:2003-08-01
    标题 :Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof

    专利号:US-2006223823-A1
    优先权日:2002-08-02
    标 题 :Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof

    专利号:US-2006217553-A1
    优先权日:2002-08-02
    标 题 :Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs 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: Lv J, Xu Y, Liu Y, Sakurai K, Yu H, Tang Z. Co-delivery of Plinabulin and Tirapazamine boosts anti-tumor efficacy by simultaneously destroying tumor blood vessels and killing tumor cells. Biomaterials. 2024 Sep;309:122586. doi: 10.1016/j.biomaterials.2024.122586. Epub 2024 Apr 30. 25(8):e202400143. doi: 10.1002/cbic.202400143. Epub 2024 Mar 22. 16(8):1153. doi: 10.3390/ph16081153.
    5: Fang S, Bi S, Li Y, Tian S, Xu H, Fu L, Wang S, Tang Y, Qiu P. Design, synthesis and anti-tumor evaluation of plinabulin derivatives as potential agents targeting β-tubulin. Bioorg Med Chem Lett. 2023 Jul 15;91:129370. doi: 10.1016/j.bmcl.2023.129370. Epub 2023 Jun 8. 35(4):241-247. doi: 10.1097/CCO.0000000000000952. Epub 2023 May 3. 14(8):773-778. doi: 10.1111/1759-7714.14806. Epub 2023 Feb 1.
    8: Chu Y, Tian Z, Yang M, Li W. Conformation and energy investigation of microtubule longitudinal dynamic instability induced by natural products. Chem Biol Drug Des. 2023 Sep;102(3):444-456. doi: 10.1111/cbdd.14189. Epub 2022 Dec 15. 13(1):6066. doi: 10.1038/s41467-022-33750-7.

    合成参考文献


    参考文献:10.2174/138945011798829366
    摘要:Spear MA, LoRusso P, Mita A, Mita M. Vascular disrupting agents (VDA) in oncology: advancing towards new therapeutic paradigms in the clinic. Curr Drug Targets. 2011 Dec;12(14):2009–15. doi: 10.2174/138945011798829366.
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