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N-(4-ethoxyphenyl)-retinamide | 53839-73-9

中文名称
——
中文别名
——
英文名称
N-(4-ethoxyphenyl)-retinamide
英文别名
4-Ethoxyphenylretinamide;n-(4-Ethoxyphenyl)retinamide;(2E,4E,6E,8E)-N-(4-ethoxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
N-(4-ethoxyphenyl)-retinamide化学式
CAS
53839-73-9
化学式
C28H37NO2
mdl
——
分子量
419.607
InChiKey
GWVFTYCSIFKPEZ-FSDIUQKZSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    188-189 °C
  • 沸点:
    595.2±42.0 °C(Predicted)
  • 密度:
    1.038±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    7.9
  • 重原子数:
    31
  • 可旋转键数:
    8
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.39
  • 拓扑面积:
    38.3
  • 氢给体数:
    1
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    维A酸吡啶六氯丙酮 、 triphenylphosphine-resin 作用下, 以 四氢呋喃 为溶剂, 反应 1.0h, 生成 N-(4-ethoxyphenyl)-retinamide
    参考文献:
    名称:
    Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs
    摘要:
    Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the main mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR. (c) 2006 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2006.10.050
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文献信息

  • Solid phase synthesis of arylretinamides
    申请人:——
    公开号:US20030105164A1
    公开(公告)日:2003-06-05
    A solid phase synthetic method for preparing arylretinamides is provided. The method comprises reacting hexachloroacetone with a solvent-suspended resin-bound triphenylphosphine to provide a suspension comprising an activated chlorinating reagent; reacting retinoic acid with the activated chlorinating reagent to provide retinoyl chloride; adding pyridine and a select arylamine to the resulting mixture; and stirring the resulting mixture for a time and at a temperature sufficient for the select arylamine to react with the retinoyl chloride and provide the arylretinamide. Also provided, are select arylretinamides that can be prepared by the present method, and methods of using such arylretinamides to induce apoptosis in cancer cells.
    提供了一种用于制备芳基维甲酰胺的固相合成方法。该方法包括将六氯乙酮与悬浮于溶剂中的树脂结合的三苯基膦反应,以提供含有活化氯化试剂的悬浮液;将维甲酸与活化氯化试剂反应以提供维甲酰氯;向得到的混合物中加入吡啶和选择的芳基胺;并在足够时间和温度下搅拌得到的混合物,以使选择的芳基胺与维甲酰氯反应并提供芳基维甲酰胺。还提供了可以通过该方法制备的选择性芳基维甲酰胺,以及使用这些芳基维甲酰胺在癌细胞中诱导凋亡的方法。
  • One-Step, Low-Cost, Operator-Friendly, and Scalable Procedure to Synthetize Highly Pure N-(4-ethoxyphenyl)-retinamide in Quantitative Yield without Purification Work-Up
    作者:Silvana Alfei、Guendalina Zuccari
    DOI:10.3390/molecules27113632
    日期:——

    It is widely reported that N-(4-hydroxyphenyl)-retinamide or fenretinide (4-HPR), which is a synthetic amide of all-trans-retinoic acid (ATRA), inhibits in vitro several types of tumors, including cancer cell lines resistant to ATRA, at 1–10 µM concentrations. Additionally, studies in rats and mice have confirmed the potent anticancer effects of 4-HPR, without evidencing hemolytic toxicity, thus demonstrating its suitability for the development of a new chemo-preventive agent. To this end, the accurate determination of 4-HPR levels in tissues is essential for its pre-clinical training, and for the correct determination of 4-HPR and its metabolites by chromatography, N-(4-ethoxyphenyl)-retinamide (4-EPR) has been suggested as an indispensable internal standard. Unfortunately, only a consultable old patent reports the synthesis of 4-EPR, starting from dangerous and high-cost reagents and using long and tedious purification procedures. To the best of our knowledge, no article existed so far describing the specific synthesis of 4-EPR. Only two vendors worldwide supply 4-ERP, and its characterization was incomplete. Here, a scalable, operator-friendly, and one-step procedure to synthetize highly pure 4-EPR without purification work-up and in quantitative yield is reported. Additionally, a complete characterization of 4-EPR using all possible analytical techniques has been provided.

    据广泛报道,作为全反式维甲酸(ATRA)的合成酰胺,N-(4-羟基苯基)维甲酸或芬瑞那酯(4-HPR)在体外浓度为 1-10 µM 时可抑制多种类型的肿瘤,包括对 ATRA 具有抗药性的癌细胞系。此外,在大鼠和小鼠身上进行的研究也证实了 4-HPR 的强效抗癌作用,而且没有溶血性毒性,因此证明它适合开发一种新的化疗预防剂。为此,准确测定 4-HPR 在组织中的含量对于其临床前培训至关重要,而为了通过色谱法正确测定 4-HPR 及其代谢物,有人建议将 N-(4-乙氧基苯基)视黄醇酰胺(4-EPR)作为不可或缺的内标。遗憾的是,只有一项可查阅的旧专利报道了 4-EPR 的合成方法,该方法从危险和高成本的试剂开始,并使用漫长而繁琐的纯化程序。据我们所知,迄今为止还没有一篇文章介绍 4-EPR 的具体合成方法。全球只有两家供应商供应 4-ERP,而且其特征描述也不完整。本文报告了一种可扩展、操作简便、一步合成高纯度 4-EPR 的方法,无需纯化工作,且产量可达到定量水平。此外,还利用所有可能的分析技术提供了 4-EPR 的完整表征。
  • Solid oral formulation of fenretinide
    申请人:LAURENT PHARMACEUTICALS
    公开号:US10406127B2
    公开(公告)日:2019-09-10
    Amorphous solid dispersions suitable for oral delivery comprising fenretinide or an analog thereof and at least one matrix polymer, and processes for making the dispersions, are disclosed. Also disclosed are solid oral formulations comprising the amorphous solid dispersions, as well as uses thereof for the prevention and/or treatment of diseases or conditions treatable by fenretinide, including but not limited to cancers, conditions associated with a lipid imbalance, cystic fibrosis, osteoporosis, conditions associated with inflammation or opportunistic infections, and other diseases such as diabetes, obesity, dry-form age-related macular degeneration.
    本发明公开了适用于口服给药的无定形固体分散体,该分散体包含芬瑞替尼或其类似物和至少一种基质聚合物,并公开了该分散体的制造工艺。还公开了包含无定形固体分散体的固体口服制剂,以及其用于预防和/或治疗可由芬雷肽治疗的疾病或病症的用途,包括但不限于癌症、与脂质失衡相关的病症、囊性纤维化、骨质疏松症、与炎症或机会性感染相关的病症,以及其他疾病,如糖尿病、肥胖症、干型老年性黄斑变性。
  • Pharmaceutical compositions of fenretinide having increased bioavailability and methods of using the same
    申请人:——
    公开号:US20020183394A1
    公开(公告)日:2002-12-05
    A pharmaceutical composition for parenteral delivery, comprising a retinide such as fenretinide in combination with a solvent capable of dispersing or solubilizing the retinide. The solvent comprises an alcohol, such as ethanol, in combination with an alkoxylated castor oil, such as CREMOPHOR® EL, or comprising a retinide, such as fenretinide, in an emulsion composed of a lipoid dispersed in an aqueous phase, a stabilizing amount of a non-ionic surfactant, optionally a solvent, and optionally an isotonic agent. In addition, a method of use in the treatment of hyperproliferative disorders, such as cancers is described.
    一种用于肠外给药的药物组合物,包括一种视黄酸(如非视黄酸)与一种能够分散或溶解视黄酸的溶剂。溶剂包括醇(如乙醇)与烷氧基化蓖麻油(如 CREMOPHOR® EL)的混合物,或包含在由分散于水相中的类脂质、稳定量的非离子表面活性剂、可选的溶剂和可选的等渗剂组成的乳液中的视黄酸(如非维甲酸)。此外,还介绍了一种用于治疗过度增殖性疾病(如癌症)的方法。
  • Fenretinide Derivatives Act as Disrupters of Interactions of Serum Retinol Binding Protein (sRBP) with Transthyretin and the sRBP Receptor
    作者:José Angel Campos-Sandoval、Clara Redondo、Gemma K. Kinsella、Akos Pal、Geraint Jones、Gwen S. Eyre、Simon C. Hirst、John B. C. Findlay
    DOI:10.1021/jm200256g
    日期:2011.7.14
    Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.
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