CAS: 93693-01-7; N-(4-Ethylphenyl)Hydrazinecarbothioamide

该化合物是一种专门的有机化合物,配以四氯苯基的细胞细胞功能组,具有独特的反应性,在混合七环化合物特别是三联苯和三联苯的过程中具有宝贵的中间作用,这些化合物对制药和农用化学研究很感兴趣,其乙基苯组会增加亲脂性,有可能提高衍生化合物的生物利用率.

结构式图片

上下游产品

(4-ethylphenyl)isothi°Cyanate carbon disulfide 4-aminoethylbenzene (Z)-N-(4-ethylphenyl)-2-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide N-(4-ethylphenyl)-2-[2-oxo-5-(trifluoromethoxy)-1,2-dihydro-3H-indol-3-ylidene]-1-hydrazinecarbothioamide N-(4-ethylphenyl)-2-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-1-hydrazinecarbothioamide 2-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N-(4-ethylphenyl)-1-hydrazinecarbothioamide

合成工艺路线路线简述

  • 合成目标产物 4-(4-Ethylphenyl)-3-Thiosemicarbazide 主要起始原料 4-Ethylphenyl Isothiocyanate
  • 18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Hydrate (1:1) Solvents: Dichloromethane; 3 H,Reflux
    标题:Novel Indol-3-Yl-Thiosemicarbazone Derivatives: Obtaining,Evaluation Of In Vitro Leishmanicidal Activity And Ultrastructural Studies
    作者:Da Silva,Paula Roberta; De Oliveira,Jamerson Ferreira; Da Silva,Anekecia Lauro; Queiroz,Camila Marques; Feitosa,Ana Paula Sampaio; Et Al
    参考文献:Chemico-Biological Interactions 日期:2020 卷标:315]

    2414962-98-2 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Hydrate (1:1); 30 °C
    标题:N-Substituted Benzaldehyde Thiosemicarbazone Derivative,And Its Preparation Method And Application In Preparing Antifungal Material
    参考文献:China]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Solvents: Dichloromethane; 2 H,25 °C
    标题:Novel 4-Quinoline-Thiosemicarbazone Derivatives: Synthesis,Antiproliferative Activity,In Vitro And In Silico Biomacromolecule Interaction Studies And Topoisomerase Inhibition
    作者:Ribeiro,Amelia Galdino; Vitalino De Almeida,Sinara Monica; Ferreira De Oliveira,Jamerson; Souza,Tulio Ricardo Couto De Lima; Lima Dos Santos,Keriolaine; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2019 卷标:182]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Hydrate (1:1) Solvents: Dichloromethane; Rt; 2 H,Rt
    标题:Synthesis Of Thiophene-Thiosemicarbazone Derivatives And Evaluation Of Their In Vitro And In Vivo Antitumor Activities
    作者:Ferreira De Oliveira,Jamerson; Lauro Da Silva,Anekecia; Vendramini-Costa,Debora Barbosa; Amorim,Cezar Augusto Da Cruz; Campos,Julia Furtado; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2015 卷标:104 页码:148-156]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Hydrate (1:1) Solvents: Ethanol; 0 °C; Overnight,0 °C
    标题:Synthesis,Molecular Modeling And Antiviral Activity Of Novel 5-Fluoro-1H-Indole-2,3-Dione 3-Thiosemicarbazones
    作者:Sevincli,Zekiye Seyma; Duran,Gizem Nur; Ozbil,Mehmet; Karali,Nilgun
    参考文献:Bioorganic Chemistry 日期:2020 卷标:104]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Solvents: Ethanol; Rt; 3 H,Cooled
    标题:Design,Synthesis And Biological Evaluation Of Novel Tetralone/indanone Containing Thiosemicarbazone Derivatives With Selective Cox-2 Inhibition As Anticancer Agents
    作者:Kuran,Ebru Didem; Dincel,Efe Dogukan; Biltekin,Sevde Nur; Akalin-Ciftci,Gulsen; Ulusoy-Guzeldemirci,Nuray
    参考文献:Journal Of Molecular Structure 日期:2023 卷标:1286]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Hydrazine Hydrate (1:1) Solvents: Methanol; 1 H,Rt
    标题:Structural Revision Of The Mcl-1 Inhibitor Mim1: Synthesis And Biological Studies On Ovarian Cancer Cells With Evaluation Of Designed Analogues
    作者:Paysant,Hippolyte; Hedir,Siham; Justaud,Frederic; Weiswald,Louis Bastien; El Dine,Assaad Nasr; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2021 卷标:19(41) 页码:8968-8987]

    589-16-2 = 93693-01-7
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dimethylformamide; 4 H,Rt1.2 Reagents: Hydrazine Hydrate (1:1); Rt -> 65 °C; 2 H,65 °C
    标题:Synthesis,Cytotoxicity,And In Vivo Antitumor Activity Study Of Parthenolide Semicarbazones And Thiosemicarbazones
    作者:Jia,Xinxin; Liu,Qi; Wang,Shiyi; Zeng,Binglin; Du,Guohua; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2020 卷标:28(13)]

    18856-63-8 = 93693-01-7
    反应条件:1.1 Reagents: Tert-Butyl Carbazate1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Synthesis And Structure-Activity Evaluation Of Isatin-β-Thiosemicarbazones With Improved Selective Activity Toward Multidrug-Resistant Cells Expressing P-Glycoprotein
    作者:Hall,Matthew D.; Brimacombe,Kyle R.; Varonka,Matthew S.; Pluchino,Kristen M.; Monda,Julie K.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2011 卷标:54(16) 页码:5878-5889
📜Tert-Butyl N-[(4-Ethylphenyl)Carbamothioylamino]Carbamate置于盐酸体系中,用 水 作为反应溶剂,化学反应生成 4-(4-乙苯基)-3-氨基硫脲
参考文献:Synthesis And Structure-activity Evaluation Of Isatin-β-Thiosemicarbazones With Improved Selective Activity Toward Multidrug-Resistant Cells Expressing P-Glycoprotein
标题:Synthesis And Structure-activity Evaluation Of Isatin-β-Thiosemicarbazones With Improved Selective Activity Toward Multidrug-Resistant Cells Expressing P-Glycoprotein
摘要:Cancer Multidrug Resistance (Mdr) Mediated By Atp-Binding Cassette (Abc) Transporters Presents A Significant Unresolved Clinical Challenge. One Strategy To Resolve Mdr Is To Develop Compounds That Selectively Kill Cells Overexpressing The Efflux Transporter P-Glycoprotein (Mdr1,P-Gp,Abcb1). We Have Previously Reported Structure-Activity Studies Based Around The Lead Compound Nsc73306 (1,1-Isatin-4-(4'-Methoxyphenyl)-3-Thiosemicarbazone,4.3-Fold Selective). Here We Sought To Extend This Work On Mdr1-Selective Analogues By Establishing Whether 1 Showed "Robust" Activity Against A Range Of Cell Lines Expressing P-Gp. We Further Aimed To Synthesize And Test Analogues With Varied Substitution At The N4-Position,And Substitution Around The N4-Phenyl Ring Of Isatin-Beta-Thiosemicarbazones (Ibts),To Identify Compounds With Increased Mdr1-Selectivity. Compound 1 Demonstrated Mdr1-Selectivity Against All P-Gp-Expressing Cell Lines Examined. This Selectivity Was Reversed By Inhibitors Of P-Gp Atpase Activity. Structural Variation At The 4'-Phenyl Position Of 1 Yielded Compounds Of Greater Mdr1-Selectivity. Two Of These Analogues,1-Isatin-4-(4'-Nitrophenyl)-3-Thiosemicarbazone (22,8.3-Fold Selective) And 1-Isatin-4-(4'-Tert-Butyl Phenyl)-3-Thiosemicarbazone (32,14.8-Fold Selective),Were Selected For Further Testing And Were Found To Retain The Activity Profile Of 1. These Compounds Are The Most Active Ibts Identified To Date.
DOI:10.1021/jm2006047

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合成参考文献


参考文献:10.1007/s11696-023-02917-x
摘要:Rani M, Devi J, Kumar B. Thiosemicarbazones-based Co(II), Ni(II), Cu(II) and Zn(II) complexes: synthesis, structural elucidation, biological activities and molecular docking. Chem. Pap. 2023 Jun 23;77(10):6007–27. doi: 10.1007/s11696-023-02917-x.
参考文献:10.1007/978-981-97-0146-9_1
摘要:Arjmand F, Tabassum S, Khan HY. Introduction. 2024. In: Advances and Prospects of 3-d Metal-Based Anticancer Drug Candidates.
参考文献:10.1134/s1070328425601013
摘要:Sasnovskaya VD, Zorina LV, Simonov SV, Zhidkov MV, Dmitriev AI, Korchagin DV, Yagubskii EB. Molecular Mn(II), Fe(III), and Dy(III) Complexes with the Pentadentate N3S2 Ligand. Russ J Coord Chem. 2025 Oct;51(10):925–35. doi: 10.1134/s1070328425601013.
参考文献:10.1007/s44371-026-00538-3
摘要:Jyothi P. Recent advances in thiosemicarbazone metal complexes: structure–activity relationship and therapeutic prospects. Discov. Chem. 2026 Feb 15;3(1). doi: 10.1007/s44371-026-00538-3.
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