(2Z,4E,6Z,8E)-3,7-二甲基-N-苯基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺 | 33631-48-0

• 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
• 中文名称: (2Z,4E,6Z,8E)-3,7-二甲基-N-苯基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺
• 英文名称: retinoic acid p-hydroxyanilide
• 英文别名: 4-HPR；fenretinide；p-hydroxyanilide RA；N-Phenylretinamide；(2E,4E,6E,8E)-3,7-dimethyl-N-phenyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• CAS: 33631-48-0
• 化学式: C₂₆H₃₃NO
• 分子量: 375.554
• InChiKey: LPUUIKWNIXVQAO-GFDJYDRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 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 (2Z,4E,6Z,8E)-3,7-二甲基-N-苯基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺
  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

• Compositions and methods for targeted enzymatic release of cell regulatory compounds
  申请人：Naleway J. John

  公开号：US20060105915A1

  公开（公告）日：2006-05-18

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

  本发明描述了新型前药及其使用方法，用于改变活细胞、组织或整个生物的生长和生物学特征。该方法允许在表达激活前药酶基因的转化宿主细胞处或其附近选择性地激活前药。根据本发明的首选实施例，前药是生物活性化合物和可被酶作用从生物活性化合物中裂解的化学基团的结合物。根据本发明的方法包括：（a）将编码酶的基因引入靶向细胞中；（b）给予前药，其中酶释放结合的前药。在本发明的首选实施例中，编码酶的基因是标记基因。
• Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
  申请人：BASF Aktiengesellschaft

  公开号：EP0009777A1

  公开（公告）日：1980-04-16

  Die Erfindung betrifft all-E- und 13-Z-Retinsäure- Verbindungen der Formel I und II, in denen die gestrichelte Linie eine chemische Bindung oder zwei Wasserstoffatome darstellt und die Carboxylgruppe am aromatischen Ring in ortho-, meta- oder p-Position stehen kann, die Herstellung dieser Verbindungen, diese Verbindungen enthaltende pharmazeutische Zubereitungen und ihre Verwendung als Arzneimittel bei der topischen und systemischen Therapie und Prophylaxe von Praekanzerosen und Karzinomen und von dermatologischen Erkrankungen.

  本发明涉及式 I 和 II 的全-E-和 13-Z-维甲酸化合物，其中 虚线代表一个化学键或两个氢原子，芳香环上的羧基可以位于正位、偏位或 p 位；本发明涉及这些化合物的制备方法、含有这些化合物的药物组合物以及它们在局部和全身治疗和预防癌前病变、癌和皮肤病中的药物用途。
• 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.
• COMPOSITIONS AND METHODS FOR TARGETED ENZYMATIC RELEASE OF CELL REGULATORY COMPOUNDS
  申请人：Marker Gene Technologies, Inc.

  公开号：EP1200131A2

  公开（公告）日：2002-05-02
• EP1390343B1
  申请人：——

  公开号：EP1390343B1

  公开（公告）日：2009-10-14