4-[3-oxo-3-(7,8-dihydro-5-(4-methylphenyl)-8.8-dimethyl-2-naphthalenyl)-1-propenyl]-benzoic acid | 188888-96-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[3-oxo-3-(7,8-dihydro-5-(4-methylphenyl)-8.8-dimethyl-2-naphthalenyl)-1-propenyl]-benzoic acid
• 英文别名: 4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid；4-[3-[8,8-dimethyl-5-(4-methylphenyl)-7H-naphthalen-2-yl]-3-oxoprop-1-enyl]benzoic acid
• CAS: 188888-96-2
• 化学式: C₂₉H₂₆O₃
• 分子量: 422.524
• InChiKey: SBFXPLUUMAMXFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[3-oxo-3-(7,8-dihydro-5-(4-methylphenyl)-8.8-dimethyl-2-naphthalenyl)-1-propenyl]-benzoic acid 在 cesium chloride 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以21%的产率得到4-[3-(8,8-dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-hydroxypropenyl]benzoic acid
  参考文献：
  名称：

  [EN] NOVEL LIGANDS THAT ARE ANTAGONISTS OF RAF RECEPTORS, PROCESS FOR PREPARING THEM AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS
  [FR] NOUVEAUX LIGANDS QUI SONT DES ANTAGONISTES DES RECEPTEURS RAR, PROCEDE DE PREPARATION DE CES LIGANDS ET UTILISATION DE CES LIGANDS DANS LES DOMAINES DE LA MEDECINE HUMAINE ET DE LA COSMETIQUE

  摘要：

  公开号：

  WO2004046096A3
• 作为产物：
  描述：

  3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene 、 对甲酰基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 13.0h， 以46%的产率得到4-[3-oxo-3-(7,8-dihydro-5-(4-methylphenyl)-8.8-dimethyl-2-naphthalenyl)-1-propenyl]-benzoic acid
  参考文献：
  名称：

  [EN] NOVEL LIGANDS THAT ARE ANTAGONISTS OF RAF RECEPTORS, PROCESS FOR PREPARING THEM AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS
  [FR] NOUVEAUX LIGANDS QUI SONT DES ANTAGONISTES DES RECEPTEURS RAR, PROCEDE DE PREPARATION DE CES LIGANDS ET UTILISATION DE CES LIGANDS DANS LES DOMAINES DE LA MEDECINE HUMAINE ET DE LA COSMETIQUE

  摘要：

  公开号：

  WO2004046096A3

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。
• Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
  申请人：——

  公开号：US20030219832A1

  公开（公告）日：2003-11-27

  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.

  取代芳基和取代芳基和（3-氧代-1-丙烯基）基苯并吡喃、苯并硫吡喃、1,2-二氢喹啉和5,6-二氢萘衍生物具有视黄醛受体负性激素和/或拮抗剂样的生物活性。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使用或联合使用，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。视黄醛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的视黄醛负性激素在体外转录激活测定中有效地增加了其他视黄醇和类固醇激素的效力。此外，转录激活测定可用于鉴定具有负性激素活性的化合物。这些测定基于负性激素降调节嵌合视黄醛受体活性的能力。
• Novel ligand antagonists of RAR receptors and pharmaceutical/cosmetic applications thereof
  申请人：Diaz Philippe

  公开号：US20050234131A1

  公开（公告）日：2005-10-20

  Novel ligand antagonists of the RAR receptors have the following structural formula (1): in which A is a CH 2 , CHOH, C═O or C═N—OH radical or a sulfur or selenium atom; B is a radical selected from among those of formulae (a) to (f): and Ar is a radical selected from among those of formulae (g) to (i):

  RAR受体的新型配体拮抗剂具有以下结构式（1）： 其中，A是CH2，CHOH，C═O或C═N—OH基团或硫或硒原子；B是从式（a）到（f）中选择的基团：Ar是从式（g）到（i）中选择的基团：
• Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities
  申请人：Allergan Sales, Inc.

  公开号：US06218128B1

  公开（公告）日：2001-04-17

  Methods of characterizing and identifying negative hormones of nuclear receptors. Also disclosed are methods of making modulators of retinoid nuclear receptor transactivation activity, assays for agonists, antagonists, and negative hormones of the RAR receptor, and specific retinoid modulators of retinoid nuclear receptors.

  表征和鉴定核受体负激素的方法。还揭示了制造视黄酸核受体转录激活活性调节剂的方法，以及RAR受体的激动剂、拮抗剂和负激素的检测方法，以及特定的视黄酸调节剂。
• Method of identifying negative hormone and/or antagonist activities
  申请人：Allergan, Inc.

  公开号：US05776699A1

  公开（公告）日：1998-07-07

  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.

  取代芳基和芳基和(3-氧代-1-丙烯基)-取代苯并吡喃、苯并硫喹啉、1,2-二氢喹啉和5,6-二氢萘衍生物具有视黄酸负性激素和/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激动剂与视黄酸药物一起或同时投与，以防止或减轻由视黄酸或视黄酸前体引起的毒性或副作用。视黄酸负性激素可用于增强其他视黄酸和核受体激动剂的活性。例如，名为AGN 193109的视黄酸负性激素在体外转录激活实验中有效增强了其他视黄酸和类固醇激素的效果。此外，转录激活实验可用于鉴定具有负性激素活性的化合物。这些实验基于负性激素通过下调带有组成性转录激活子域的嵌合视黄酸受体的活性的能力。