(2E,4E,6E,8E)-N-(4-chlorophenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide | 53839-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,4E,6E,8E)-N-(4-chlorophenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• 英文别名: (2E,4E,6E,8E)-N-(4-chlorophenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• CAS: 53839-75-1
• 化学式: C₂₆H₃₂ClNO
• 分子量: 409.999
• InChiKey: CUXARGPDBXRSOD-FXILSDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  维A酸 在 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 (2E,4E,6E,8E)-N-(4-chlorophenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
  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

文献信息

• C-linked glucuronide of N-(4-hydroxybenzyl) retinone, analogs thereof, and method of using the same to inhibit neoplastic cell growth
  申请人：Clagett-Dame Margaret

  公开号：US20060287255A1

  公开（公告）日：2006-12-21

  Compounds of the formula: are described, along with pharmaceutical compositions containing these compounds, and methods of using the compounds to prevent and to treat cancer in mammals, including humans.

  公式的化合物： 被描述，以及包含这些化合物的药物组合物，以及使用这些化合物预防和治疗哺乳动物，包括人类的癌症的方法。
• Design, Synthesis, Radiosynthesis and Biological Evaluation of Fenretinide Analogues as Anticancer and Metabolic Syndrome‐Preventive Agents
  作者：Ilaria Patruno、Dawn Thompson、Sergio Dall'Angelo、Albert D. Windhorst、Danielle J. Vugts、Alex J. Poot、Nimesh Mody、Matteo Zanda

  DOI：10.1002/cmdc.202000143

  日期：2020.8.19

  describe the preparation of a library of 4‐HPR analogues, followed by the biological evaluation of their anti‐cancer and anti‐obesity/diabetic properties. The click‐type analogue 3 b showed good capacity to reduce the amount of lipid accumulation in 3T3‐L1 adipocytes during differentiation. Furthermore, it showed an IC50 of 0.53±0.8 μM in cell viability tests on breast cancer cell line MCF‐7, together

  Fenretinide（4-HPR）是全反式视黄酸（ATRA）的合成衍生物，具有相对于ATRA更高的治疗特性和毒理学特征。4-HPR作为抗癌药已被广泛研究，但最近的研究表明，4-HPR在预防代谢综合征方面具有广阔的前景。4-HPR的活性涉及多个生物学靶标，导致该分子可能用于治疗不同的病理学。然而，尽管4-HPR在药理学方面显示出了很好理解的多靶点混杂性，但解释其确切的生理作用仍然具有挑战性。此外，尽管体外试验结果令人满意，到目前为止，4-HPR作为化学治疗剂的临床疗效尚不令人满意。本文中，我们描述了4-HPR类似物文库的制备，然后对其抗癌和抗肥胖/糖尿病特性进行了生物学评估。点击型类似物3b在分化过程中显示出良好的能力来减少3T3-L1脂肪细胞中脂质的积累。此外，在乳腺癌细胞系MCF-7的细胞活力测试中，IC 50为0.53±0.8μM，并且对非癌性HEK293细胞具有良好的选择性（SI =
• FENRETINIDE DERIVATIVES AND USES THEREOF AS THERAPEUTIC, DIAGNOSTIC AND IMAGING AGENTS
  申请人：Kalpana Ganjam V.

  公开号：US20110091383A1

  公开（公告）日：2011-04-21

  Synthetic peptidomimetic derivatives and phenyl group derivatives of Fenretinide (4-HPR) are disclosed, as are their uses as therapeutic, diagnostic and imaging agents for cancer and other diseases.

  本发明涉及Fenretinide（4-HPR）的合成肽类模拟衍生物和苯基衍生物，以及它们作为治疗、诊断和肿瘤及其他疾病成像剂的用途。
• C-LINKED GLUCORONIDE OF N-(4-HYDROXYBENZYL) RETINONE, ANALOGS THEREOF, AND METHOD OF USING THE SAME TO INHIBIT NEOPLASTIC CELL GROWTH
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP1891085A2

  公开（公告）日：2008-02-27
• C-LINKED GLUCURONIDE OF N-(4-HYDROXYBENZYL) RETINONE, ANALOGS THEREOF, AND METHOD OF USING THE SAME TO INHIBIT NEOPLASTIC CELL GROWTH
  申请人：Clagett-Dame Margaret

  公开号：US20090215706A1

  公开（公告）日：2009-08-27

  Compounds of the formula: are described, along with pharmaceutical compositions containing these compounds, and methods of using the compounds to prevent and to treat cancer in mammals, including humans.