N-(4-hydroxyphenyl)-all-trans-retinamide | 231301-45-4

• 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: N-(4-hydroxyphenyl)-all-trans-retinamide
• 英文别名: N-(4-Hydroxyphenyl)all-trans-retinamide；4-(All-trans-Retinoyl)-Aminophenol；4-(all-trans-retinoyl)aminophenol；(2E,4E,6Z,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• CAS: 231301-45-4
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: AKJHMTWEGVYYSE-WXSOSVMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 N-(4-hydroxyphenyl)-all-trans-retinamide 在 氮 作用下， 以 吡啶 为溶剂， 生成 N-(4-n-Butyryloxyphenyl)-all-trans-Retinamide
  参考文献：
  名称：

  Novel retinoids and their use in preventing carcinogenesis

  摘要：

  新型N-(4-酰氧基苯基)-全反式视黄醛酰胺化合物对于预防哺乳动物上皮癌具有用处。

  公开号：

  US04310546A1

文献信息

• Novel retinoid derivatives and methods for producing said compounds and anti-cancer pharmaceutical composition comprising said compounds
  申请人：——

  公开号：US20030171339A1

  公开（公告）日：2003-09-11

  The present invention relates to a novel retinoid derivative compound represented by the formula I: 1 wherein X, R 1 , R 2 and R 3 are as defined herein or pharmaceutically acceptalbe salts thereof. Also, the present invention relates to processes for producing the compound of the formula I and to an anti-cancer composition comprising the compound of the formula I. The compound of the formula I according to the present invention exerts high anti-cancer effects while not causing undesirable side effects.

  本发明涉及一种由公式I表示的新型维甲酸衍生物化合物，其中X、R1、R2和R3如本文所定义，或其药用可接受盐。此外，本发明涉及制备公式I化合物的方法，以及包括公式I化合物的抗癌组合物。根据本发明的公式I化合物具有高抗癌效果，同时不会引起不良副作用。
• Method to incorporate N-(4-hydroxyphenyl) retinamide in liposomes
  申请人：Board of Regents, The University of Texas System

  公开号：US20020143062A1

  公开（公告）日：2002-10-03

  Disclosed herein are simple and unique methods of methods of preparing liposomal compositions of N-(4-hydroxyphenyl) retinamide (4HPR) and/or other retinoids. Also disclosed are liposomal 4HPR compositions prepared by such methods, and use of such compositions in the treatment of diseases, such as breast cancer. This invention further provides methods for improving the efficacy of N-(4-hydroxyphenyl) retinamide (4HPR) as a chemopreventive agent in the presence of agents that potentiates its ability increase the expression of inducible nitric oxide synthase (iNOS, and NO production in cells.

  本文披露了制备N-(4-羟基苯基)视黄酰胺（4HPR）和/或其他视黄醇脂质体组合物的简单且独特的方法。还披露了通过这些方法制备的脂质体4HPR组合物，并将这种组合物用于治疗疾病，如乳腺癌。本发明还提供了一种方法，通过增强诱导型一氧化氮合酶（iNOS）和细胞内NO产生的能力，提高N-(4-羟基苯基)视黄酰胺（4HPR）作为化学预防剂的功效。
• A method for chemoprevention of prostate cancer
  申请人：THE UNIVERSITY OF TENNESSEE RESEARCH CORPORATION

  公开号：EP1475087A2

  公开（公告）日：2004-11-10

  This invention relates to the chemoprevention of prostate cancer and, more particularly, provides the use of a chemopreventive agent, e.g. toremifene and analogs or metabolites thereof, in the manufacture of a pharmaceutical preparation to prevent recurrence of, suppress or inhibit prostate carcinogenesis. The present invention provides a safe and effective method for suppressing or inhibiting latent prostate cancer and is particularly useful for treating subjects having an elevated risk of developing prostate cancer, for example, those having benign prostatic hyperplasia, prostate intraepithelial neoplasia (PIN), or an abnormally high level of circulating prostate specific antibody (PSA), or who have a family history of prostate cancer.

  本发明涉及前列腺癌的化学预防，更具体地说，提供了一种化学预防剂，如托瑞米芬及其类似物或代谢物在制造药物制剂中的用途，以防止前列腺癌复发、抑制或抑制前列腺癌的发生。本发明提供了一种安全有效的抑制或抑制潜伏前列腺癌的方法，特别适用于治疗前列腺癌发病风险升高的受试者，例如，良性前列腺增生、前列腺上皮内瘤变（PIN）或循环前列腺特异性抗体（PSA）水平异常高的受试者，或有前列腺癌家族史的受试者。
• Compositions and methods for treating hyperproliferative disorders
  申请人：TEXAS TECH UNIVERSITY

  公开号：EP2669267A1

  公开（公告）日：2013-12-04

  A method of treating a hyperproliferative disorder in a subject in need of such treatment, comprising administering to said subject, in combination, a treatment effective amount of: (a) a ceramide-increasing retinoid such as fenretinide or a pharmaceutically acceptable salt thereof; and (b) at least one (and in certain embodiments at least two) compounds selected from the groups consisting of (i) a non-18 carbon chain length L-threo-sphinganine(s) or pharmaceuticeutically acceptable salt thereof, (ii) glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor(s), and (iii) sphingomyelin or dihydrosphingomyelin synthase inhibitor(s). Preferred L-threo-sphinganines are of carbon chain length 17 carbons, 19 carbons and 20 carbons. A preferred glucosylceramide or glucosyl(dihydro)ceramide synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol.; A preferred sphingomyelin or dihydrosphingomyelin synthesis inhibitor is D-threo-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol. A preferred hyperproliferative disorder is brain cancers.

  一种治疗需要这种治疗的受试者的过度增殖性疾病的方法，包括向所述受试者联合施用治疗有效量的以下物质：(a) 神经酰胺增加型维甲酸，如芬瑞替尼或其药学上可接受的盐；(b) 至少一种（在某些实施方案中至少两种）选自以下组别的化合物：(i) 非 18 碳链长度的 L-苏-鞘氨醇或其药学上可接受的盐；(ii) 葡萄糖甘油酰胺或葡萄糖（二氢）神经酰胺合成抑制剂；(iii) 鞘磷脂或二氢鞘磷脂合成酶抑制剂。优选的 L-硫代鞘磷脂的碳链长度为 17 碳、19 碳和 20 碳。一种优选的葡糖基甘油酰胺或葡糖基（二氢）神经酰胺合成抑制剂是 D-苏-1-苯基-2-棕榈酰氨基-3-吗啉基-1-丙醇；一种优选的鞘磷脂或二氢鞘磷脂合成抑制剂是 D-苏-1-苯基-2-棕榈酰氨基-3-吗啉基-1-丙醇。一种优选的过度增殖性疾病是脑癌。
• 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。