4-[(5,6,7,8-四氢-5,5-二甲基-8-氧代-2-萘)乙炔]苯甲酸乙酯 | 166978-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 4-[(5,6,7,8-四氢-5,5-二甲基-8-氧代-2-萘)乙炔]苯甲酸乙酯
• 英文名称: ethyl 4-[(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoate
• 英文别名: ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)-ethynyl]benzoate；4-[[(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo)-2-naphthalenyl]ethynyl]benzoic acid, ethyl ester；ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl) ethynyl]benzoate；ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate；4-[2-(5,6,7,8-Tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl]benzoic acid ethyl ester；ethyl 4-[2-(5,5-dimethyl-8-oxo-6,7-dihydronaphthalen-2-yl)ethynyl]benzoate
• CAS: 166978-49-0
• 化学式: C₂₃H₂₂O₃
• 分子量: 346.426
• InChiKey: HKLPOHJGESDTSC-UHFFFAOYSA-N

物化性质

• 熔点：
  >147oC (dec.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(5,6,7,8-四氢-5,5-二甲基-8-氧代-2-萘)乙炔]苯甲酸乙酯 在 四(三苯基膦)钯 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-chlorophenyl)-2-naphthalenyl)ethynyl]benzoate
  参考文献：
  名称：

  High affinity retinoic acid receptor antagonists: Analogs of AGN 193109

  摘要：

  A series of high affinity retinoic acid receptor (RAR) antagonists were prepared based upon the known antagonist AGN 193109 (2). Introduction of various phenyl groups revealed a preference for substitution at the para-position relative to the meta-site. Antagonists with the highest affinities for the RARs possessed hydrophobic groups, however, the presence of polar functionality was also well tolerated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00047-5
• 作为产物：
  描述：

  4,4-Dimethyl-7-trimethylsilanylethynyl-1-tetralone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二乙胺 作用下， 以 甲醇 为溶剂， 生成 4-[(5,6,7,8-四氢-5,5-二甲基-8-氧代-2-萘)乙炔]苯甲酸乙酯
  参考文献：
  名称：

  视黄酸受体的高效有效拮抗剂的合成与表征。

  摘要：

  DOI：

  10.1021/jm00024a003

文献信息

• Synthesis and use of retinoid compounds having negative hormone and/or
  申请人：Allergan Sales, Inc.

  公开号：US05877207A1

  公开（公告）日：1999-03-02

  Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity. These assays are based on the ability of negative hormones to down-regulate the activity of chimeric retinoid receptors engineered to possess a constitutive transcription activator domain.

  芳基取代和芳基和（3-氧代-1-丙烯基）取代的苯并吡喃、苯并硫吡喃、1,2-二氢喹啉和5,6-二氢萘衍生物具有视黄醇负性激素和/或拮抗剂样生物活性。所发明的RAR拮抗剂可用于哺乳动物，包括人类，以防止或减轻RAR激动剂对结合受体位点的作用。具体而言，RAR激动剂可与视黄醇药物一起给予或联合给予，以防止或减轻视黄醇或维生素A或维生素A前体引起的毒性或副作用。视黄醇负性激素可用于增强其他视黄醇和核受体激动剂的活性。例如，名为AGN 193109的视黄醇负性激素在体外转录激活实验中有效增加了其他视黄醇和类固醇激素的效力。此外，转录激活实验可用于识别具有负性激素活性的化合物。这些实验基于负性激素调节具有构成转录激活子结构域的嵌合视黄醇受体活性的能力。
• Method for inhibiting gene expression promoted by AP1 protein with
  申请人：Allergan Sales, Inc.

  公开号：US06025388A1

  公开（公告）日：2000-02-15

  Retinoid compounds which repress expression of the gene promoted by AP1 protein but which do not significantly activate expression of the genes having RA-responsive elements in their promoter region through RAR.alpha. and RAR.GAMMA. receptor subtypes, are used, with reduced side effects, for treating diseases and conditions which are responsive to therapy with retinoids.

  抑制由AP1蛋白促进的基因表达，但不显著激活在其启动子区域中具有RA响应元件的基因表达（通过RAR.alpha和RAR.GAMMA受体亚型），可用于治疗对维甲酸类药物治疗产生响应的疾病和症状，且具有减少副作用。
• [EN] BENZOPYRAN AND BENZOTHIOPYRAN DERIVATIVES HAVING RETINOID ANTAGONIST-LIKE ACTIVITY<br/>[FR] DERIVES DE BENZOPYRANE ET BENZOTHYOPYRANE PRESENTANT UNE ACTIVITE RETINOÏDE DE TYPE ANTAGONISTE
  申请人：ALLERGAN SALES, INC.

  公开号：WO1999033821A1

  公开（公告）日：1999-07-08

  (EN) 2,2-Dialkyl- 4-aryl-substituted benzopyran and benzothiopyran derivatives of formula (I) where the symbols have the meaning described in the specification, have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action or RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists.(FR) L'invention concerne des dérivés de 2,2-dialkyl-benzopyrane et benzothiopyrane à substitution 4-aryl de formule (I), dont les symboles sont définis dans le descriptif. Ces dérivés présentent des activités biologiques rétinoïdes de type antagonistes et/ou hormones négatives. Les antagonistes de RAR de l'invention peuvent être administrés aux mammifères, y compris aux humains, pour prévenir ou réduire l'action d'antagonistes de RAR sur les sites récepteurs liés. En particulier, les agonistes de RAR sont administrés ou co-administrés avec des médicaments rétinoïdes pour empêcher ou atténuer la toxicité ou les effets secondaires des rétinoïdes, de la vitamine A ou des précurseurs de la vitamine A. Les hormones négatives rétinoïdes peuvent être utilisées pour renforcer les activités d'autres rétinoïdes et celles d'agonistes de récepteurs nucléaires.

  2,2-二烷基-4-芳基取代苯并吡喃和苯并噻吩的衍生物，其化学式为(I)，其中符号的含义在说明书中描述，具有视黄醇负性激素和/或拮抗剂样生物活性。发明的RAR拮抗剂可用于哺乳动物，包括人类，以防止或减少RAR激动剂对结合受体位点的作用。具体而言，RAR激动剂与视黄醇药物一起给予或联合给予，以防止或缓解视黄醇或维生素A或维生素A前体引起的毒性或副作用。视黄醇负性激素可用于增强其他视黄醇和核受体激动剂的活性。
• Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group
  申请人：Allergan

  公开号：US05605915A1

  公开（公告）日：1997-02-25

  Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification.

  式子为##STR1##的化合物，其中符号的含义在规范中定义。
• Acetylenes disubstituted with a 5 OXO substituted tetrahydronaphthyl
  申请人：Allergan

  公开号：US05618943A1

  公开（公告）日：1997-04-08

  Compounds of the formula ##STR1## the symbols have the meaning described in the specification have retinoid-like biological activity.

  式子为##STR1##的化合物，其中符号的含义在说明书中有描述，具有类视黄醇的生物活性。