CAS: 865536-65-8; (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-Dimethyl-9-(2,6,6-Trimethyl-3-Oxocyclohex-1-En-1-yl)Nona-2,4,6,8-Tetraenamide

该化合物是一种合成化合物,属于维生素A衍生物的视质素类别.该物质具有经氨基基组和氢氧联苯运动改造的视网膜骨干,有助于其独特的化学特性.氢氧联苯团体的存在增强了其生物活动潜力,特别是在视觉过程和细胞信号路径方面的潜力.该化合物的特点是它能够与特定受体互动,有可能影响基因表达和细胞差异.其结构特征还可能带来稳定性和溶性特征,与药物应用有关.作为视网膜的模拟,它可能表现出抗氧化性特性,并在调节各种生理功能方面发挥作用.该化合物的研究可能侧重于其治疗潜力,特别是在与视觉和皮肤健康有关的领域,尽管具体的生物活动和机制需要进一步调查.

结构式图片

物理性质

MSDS等安全信息

合成工艺路线路线简述

  • 38030-57-8 = 865536-65-8
    反应条件:1.1 Reagents: Hexachloroacetone,Triphenylphosphine Solvents: Dichloromethane; -78 °C1.2 Reagents: Pyridine; Rt
    标题:Water-Soluble Derivatives Of 4-Oxo-N-(4-Hydroxyphenyl) Retinamide: Synthesis And Biological Activity
    作者:Musso,Loana; Et Al
    参考文献:Chemical Biology & Drug Design 日期:2016 卷标:88(4) 页码:608-614]

    38030-58-9 = 865536-65-8
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol; 5 H,Rt2.1 Reagents: Hexachloroacetone,Triphenylphosphine Solvents: Dichloromethane; -78 °C2.2 Reagents: Pyridine; Rt
    标题:Water-Soluble Derivatives Of 4-Oxo-N-(4-Hydroxyphenyl) Retinamide: Synthesis And Biological Activity
    作者:Musso,Loana; Et Al
    参考文献:Chemical Biology & Drug Design 日期:2016 卷标:88(4) 页码:608-614]

    = 865536-65-8
    反应条件:1.1 Reagents: Manganese Oxide (Mno2) Solvents: Dichloromethane; 24 H,Rt2.1 Reagents: Sodium Hydroxide Solvents: Methanol; 5 H,Rt3.1 Reagents: Hexachloroacetone,Triphenylphosphine Solvents: Dichloromethane; -78 °C3.2 Reagents: Pyridine; Rt
    标题:Water-Soluble Derivatives Of 4-Oxo-N-(4-Hydroxyphenyl) Retinamide: Synthesis And Biological Activity
    作者:Musso,Loana; Et Al
    参考文献:Chemical Biology & Drug Design 日期:2016 卷标:88(4) 页码:608-614]

    302-79-4 + 18107-18-1 = 865536-65-8
    反应条件:1.1 Solvents: Methanol,Toluene; 45 Min,Rt2.1 Reagents: Manganese Oxide (Mno2) Solvents: Dichloromethane; 24 H,Rt3.1 Reagents: Sodium Hydroxide Solvents: Methanol; 5 H,Rt4.1 Reagents: Hexachloroacetone,Triphenylphosphine Solvents: Dichloromethane; -78 °C4.2 Reagents: Pyridine; Rt
    标题:Water-Soluble Derivatives Of 4-Oxo-N-(4-Hydroxyphenyl) Retinamide: Synthesis And Biological Activity
    作者:Musso,Loana; Et Al
    参考文献:Chemical Biology & Drug Design 日期:2016 卷标:88(4) 页码:608-614

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主要参考文献


1: Tiberio P, Cavadini E, Cleris L, Dallavalle S, Musso L, Daidone MG, Appierto V. Sodium 4-Carboxymethoxyimino-(4-HPR) a Novel Water-Soluble Derivative of 4-Oxo-4-HPR Endowed with In Vivo Anticancer Activity on Solid Tumors. Front Pharmacol. 2017 Apr 26;8:226. doi: 10.3389/fphar.2017.00226. eCollection 2017.
2: Poliakov E, Samuel W, Duncan T, Gutierrez DB, Mata NL, Redmond TM. Inhibitory effects of fenretinide metabolites N-[4-methoxyphenyl]retinamide (MPR) and 4-oxo-N-(4-hydroxyphenyl)retinamide (3-keto-HPR) on fenretinide molecular targets β-carotene oxygenase 1, stearoyl-CoA desaturase 1 and dihydroceramide Δ4-desaturase 1. PLoS One. 2017 Apr 27;12(4):e0176487. doi: 10.1371/journal.pone.0176487. eCollection 2017.
3: Lopez-Barcons L, Maurer BJ, Kang MH, Reynolds CP. P450 inhibitor ketoconazole increased the intratumor drug levels and antitumor activity of fenretinide in human neuroblastoma xenograft models. Int J Cancer. 2017 Jul 15;141(2):405-413. doi: 10.1002/ijc.30706. Epub 2017 May 9. doi: 10.1016/j.jpba.2016.09.046. Epub 2016 Sep 29.

合成参考文献


参考文献:10.1158/1535-7163.mct-09-0798
摘要:Appierto V, Tiberio P, Cavadini E, Casalini P, Cappelletti G, Formelli F. Antimitotic effect of the retinoid 4-oxo-fenretinide through inhibition of tubulin polymerization: a novel mechanism of retinoid growth-inhibitory activity. Mol Cancer Ther. 2009 Dec;8(12):3360–8. doi: 10.1158/1535-7163.mct-09-0798.
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