2-(4-碘苯基)-(3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-基)-甲酮 | 926038-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-碘苯基)-(3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-基)-甲酮
• 英文名称: 2-(4-iodophenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methanone
• 英文别名: (4-Iodophenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methanone；(4-iodophenyl)-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)methanone
• CAS: 926038-65-5
• 化学式: C₂₂H₂₅IO
• 分子量: 432.344
• InChiKey: JPDVFAGZXWFAFL-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-碘苯基)-(3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-基)-甲酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium hydrogen difluoride 、 potassium acetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.75h， 生成 potassium (4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)phenyl)trifluoroborate
  参考文献：
  名称：

  Synthesis of [¹¹C]Bexarotene by Cu-Mediated [¹¹C]Carbon Dioxide Fixation and Preliminary PET Imaging

  摘要：

  Bexarotene (Targretin) is a retinoid X receptor (RXR) agonist that has applications for treatment of T cell lymphoma and proposed mechanisms of action in Alzheimer's disease that have been the subject of recent controversy. Carbon-11 labeled bexarotene ([11C_ carbony1]4-[1-(3,5,5,8,8-pentamethylietralin-2-yOethenyllbenzoic acid) was synthesized using a Cu-mediated cross-coupling reaction employing an arylboronate precursor 1 and [C-11]carbon dioxide under atmospheric pressure in 15 +/- 2% uncorrected radiochemical yield (n = 3), based on [C-11]CO2. Judicious choice of solvents, catalysts, and additives, as well as precursor concentration and purity of [11C]CO2, enabled the preparation of this C-11-labeled carboxylic acid. Formulated [11C]bexarotene was isolated (>37 mCi) with >99% radiochemical purity in 32 mm. Preliminary positron emission tomography magnetic resonance imaging revealed rapid brain uptake in nonhuman primate in the first 75 s following intravenous administration of the radiotracer (specific activity >0.3 Ci/mu mol at time of injection), followed by slow clearance (Delta = 43%) over 60 min. Modest uptake (SUV = 0.8) was observed in whole brain and regions with high RXR expression.

  DOI：

  10.1021/ml500065q
• 作为产物：
  描述：

  1,1,4,4,6-五甲基-1,2,3,4-四氢化萘 、 4-碘苯甲酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以71%的产率得到2-(4-碘苯基)-(3,5,5,8,8-五甲基-5,6,7,8-四氢萘-2-基)-甲酮
  参考文献：
  名称：

  WO2007/22437

  摘要：

  公开号：

文献信息

• Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders
  申请人：Sarshar Sepehr

  公开号：US20080234229A1

  公开（公告）日：2008-09-25

  The present invention is directed to compounds having the structure Formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 and m are as defined herein. The compounds of this invention are novel therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders in mammalian subjects. These compounds are also useful modulators of gene expression. They exert their activity by interfering with certain cellular signal transduction cascades. The compounds of the invention are thus also useful for regulating cell differentiation and cell cycle processes that are controlled or regulated by various hormones or cytokines. In particular, the invention relates to compounds that induce apoptosis of cancer cells and therefore may be used for the treatment or prevention of cancer, including advanced cancers and pre-cancerous cells. The invention also discloses pharmaceutical compositions and methods of treatment of disease in mammals.

  本发明涉及具有结构式（I）的化合物，其中R1、R2、R3、R4、R5和m的定义如本文所述。本发明的化合物是哺乳动物主体中治疗癌症、代谢性疾病和皮肤疾病的新型治疗剂。这些化合物也是有用的基因表达调节剂。它们通过干扰某些细胞信号转导级联来发挥作用。因此，本发明的化合物也有助于调节由各种激素或细胞因子控制或调节的细胞分化和细胞周期过程。特别是，本发明涉及诱导癌细胞凋亡的化合物，因此可用于治疗或预防癌症，包括晚期癌症和癌前细胞。本发明还揭示了哺乳动物疾病的药物组成和治疗方法。
• ACS Med. Chem. Lett. 2014, 5, 668-672
  作者：

  DOI：——

  日期：——
• [EN] NOVEL THERAPEUTIC AGENTS FOR THE TREATMENT OF CANCER, METABOLIC DISEASES AND SKIN DISORDERS<br/>[FR] NOUVEAUX AGENTS THÉRAPEUTIQUES POUR LE TRAITEMENT DE CANCERS, DE MALADIES MÉTABOLIQUES ET DE TROUBLES CUTANÉS
  申请人：AUSPEX PHARMACEUTICALS INC

  公开号：WO2007022437A2

  公开（公告）日：2007-02-22

  [EN] The present invention is directed to compounds having the structure Formula (I) wherein R₁, R₂, R₃, R₄, R₅ and m are as defined herein. The compounds of this invention are novel therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders in mammalian subjects. These compounds are also useful modulators of gene expression. They exert their activity by interfering with certain cellular signal transduction cascades. The compounds of the invention are thus also useful for regulating cell differentiation and cell cycle processes that are controlled or regulated by various hormones or cytokines. In particular, the invention relates to compounds that induce apoptosis of cancer cells and therefore may be used for the treatment or prevention of cancer, including advanced cancers and pre-cancerous cells. The invention also discloses pharmaceutical compositions and methods of treatment of disease in mammals.
  [FR] La présente invention concerne des composés dont la structure répond à la Formule (I) où R₁, R₂, R₃, R₄, R₅ et m sont tels que définis dans la description de l'invention. Les composés selon cette invention sont de nouveaux agents thérapeutiques destinés au traitement de cancers, de maladies métaboliques et de troubles cutanés chez des sujets mammifères. Ces composés peuvent également être employés en tant que modulateurs de l'expression des gènes. Leur activité s'exerce par interférence avec certaines cascades de transduction de signal cellulaire. Les composés selon l'invention peuvent donc également être employés pour réguler les processus de différentiation cellulaire et de cycle cellulaire contrôlés ou régulés par diverses hormones ou cytokines. En particulier, la présente invention concerne des composés qui induisent l'apoptose de cellules cancéreuses, et peuvent donc être employés dans le traitement prophylactique ou thérapeutique de cancers, y compris de cancers avancés et de cellules pré-cancéreuses. La présente invention décrit également des préparations pharmaceutiques et des méthodes de traitement de maladies chez les mammifères.