4-(1-羟基-3-氧-3-(5,6,7,8-四氢-3-羟基-5,5,8,8-四甲基-2-萘基)-1-丙烯基)苯甲酸 | 116193-60-3

• 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
• 中文名称: 4-(1-羟基-3-氧-3-(5,6,7,8-四氢-3-羟基-5,5,8,8-四甲基-2-萘基)-1-丙烯基)苯甲酸
• 英文名称: 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid
• 英文别名: 4-<1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl>benzoic acid；Re80；4-(1-Hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl)benzoic acid；4-[(Z)-1-hydroxy-3-(3-hydroxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 116193-60-3
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: PZYFNWUXYUMHGR-UYRXBGFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯甲酰基苯甲酸甲酯 在 吡啶 、 氢氧化钾 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(1-羟基-3-氧-3-(5,6,7,8-四氢-3-羟基-5,5,8,8-四甲基-2-萘基)-1-丙烯基)苯甲酸
  参考文献：
  名称：

  Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids

  摘要：

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.

  DOI：

  10.1021/jm00124a016

文献信息

• Use of synthetic retinoids for osteopathy
  申请人：HOECHST JAPAN LIMITED

  公开号：EP0619116A2

  公开（公告）日：1994-10-12

  An anti-osteopathic composition comprising as an active ingredient a compound represented by the following formula (I), (II) or (III): which is useful for therapeutic and prophylactic treatment of osteopathia such as osteoporosis and bone fracture.

  一种抗骨病组合物，其活性成分包括下式（I）、（II）或（III）所代表的化合物： 可用于治疗和预防骨质疏松症，如骨质疏松症和骨折。
• CANCEROUS METASTASIS INHIBITOR
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：EP0768084A1

  公开（公告）日：1997-04-16

  A cancerous metastasis inhibitor containing a benzoic acid derivative which is represented by general formula (I) and has a remarkably excellent cancerous metastasis inhibitory effect as the active ingredient; the use of the benzoic acid derivatives for producing the cancerous metastasis inhibitor; and a method of inhibiting cancerous metastasis by administering an effective amount of the benzoic acid derivative to mammals. In said formula (I), R1, R2, R3 and R4 may be the same or different and each represents hydrogen, hydroxy or trimethylsilyl, or alternatively R3 and R4 are bonded to each other to represent lower alkyl-substituted tetramethylene; and X represents -COCH=C(OH)-, -NHCO-or -CONH-, provided when R3 and R4 are bonded to each other to represent lower alkyl-substituted tetramethylene, X represents -COCH=C(OH)- or -CONH-.

  一种含有苯甲酸衍生物的癌症转移抑制剂，其活性成分由通式（I）表示，具有显著优异的癌症转移抑制效果；使用苯甲酸衍生物生产癌症转移抑制剂；以及通过向哺乳动物施用有效量的苯甲酸衍生物来抑制癌症转移的方法。在所述式(I)中，R1、R2、R3和R4可以相同或不同，各自代表氢、羟基或三甲基硅基，或者R3和R4相互键合代表低级烷基取代的四亚甲基；X代表-COCH＝C(OH)-、-NHCO-或-CONH-，条件是当R3和R4相互键合代表低级烷基取代的四亚甲基时，X代表-COCH＝C(OH)-或-CONH-。
• RAR selective agonists in combination with immune modulators for cancer immunotherapy
  申请人：Io Therapeutics, Inc.

  公开号：US10363272B2

  公开（公告）日：2019-07-30

  Disclosed herein are methods for treating cancer comprising administering CAR-modified immune cells and at least one Retinoic Acid Receptor agonist.

  本文公开了治疗癌症的方法，包括给药 CAR 修饰的免疫细胞和至少一种视黄酸受体激动剂。
• Immunomodulatory and differentiating function selective retinoid and rexinoid compounds in combination with immune modulators for cancer immunotherapy
  申请人：Io Therapeutics, Inc.

  公开号：US10471030B2

  公开（公告）日：2019-11-12

  Disclosed herein are methods for treating cancer comprising administering CAR-modified immune cells and at least one Retinoic Acid Receptor and/or Retinoid X Receptor active agent.

  本文公开了治疗癌症的方法，包括给药 CAR 修饰的免疫细胞和至少一种视黄酸受体和/或视黄醇 X 受体活性剂。
• Use of CYP26-resistant RAR alpha selective agonists in the treatment of cancer
  申请人：Io Therapeutics, Inc.

  公开号：US10940127B2

  公开（公告）日：2021-03-09

  Disclosed herein are methods for treating a cancer comprising administering to a subject in need thereof an effective dose of a CYP26-resistant retinoic acid receptor (RAR) alpha (RARα) selective agonist, whereby as a result of the treatment the tumor burden is reduced in the subject and cancer stem cells resident in the bone marrow are substantially reduced.

  本文公开了治疗癌症的方法，包括向有需要的受试者施用有效剂量的抗CYP26维甲酸受体（RAR）α（RARα）选择性激动剂，治疗的结果是减轻受试者的肿瘤负担，并大大减少骨髓中的癌症干细胞。