5',5',8',8'-四甲基-5',6',7',8'-四氢-2,2'-联萘-6-羧酸 | 86471-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5',5',8',8'-四甲基-5',6',7',8'-四氢-2,2'-联萘-6-羧酸
• 英文名称: 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthoic acid
• 英文别名: 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-6-naphthalene carboxylic acid；Ro 19-0645；6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acid；5',5',8',8'-tetramethyl-5',6',7',8'-tetrahydro-[ 2,2']binaphthalenyl-6-carboxylic acid；6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid
• CAS: 86471-16-1
• 化学式: C₂₅H₂₆O₂
• 分子量: 358.48
• InChiKey: UHFICAKXFHFOCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-溴-2-萘甲酸乙酯 在 氢氧化钾 、 四(三苯基膦)镍 、 lithium 、 zinc(II) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 5',5',8',8'-四甲基-5',6',7',8'-四氢-2,2'-联萘-6-羧酸
  参考文献：
  名称：

  Synthesis and pharmacological activity of 6-[(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl)]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids

  摘要：

  6-[(E)-2-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids (4 and 8) have been synthesized and show significant activity in reversing the keratinization process in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse skin by 12-O-tetradecanoylphorbol-13-acetate, two assays used to measure retinoid activity. The 2-naphthalenecarboxylic acid 8 was more active than 4.

  DOI：

  10.1021/jm00365a021

文献信息

• Use of a RAR-gamma-specific agonist ligand for increasing the rate of apoptosis
  申请人：——

  公开号：US20030092758A1

  公开（公告）日：2003-05-15

  The present invention relates to the use of at least one RAR receptor agonist ligand, particularly 6-[3-(adamantan-1-yl)-4-(prop-2-ynyloxy)phenyl]naphthalene-2-carboxylic acid or 5-[(E)-3-oxo-3-(5,5,8,8-tetrahydronaphthalene-2-yl)propenyl]thiophene-2-carboxylic acid, to prepare a pharmaceutical composition for increasing the rate of apoptosis in at least one cell population in which apoptosis may be induced by activating RAR-&ggr; receptors. The composition is particularly useful for treating a disease or disorder related to an insufficient rate of apoptosis in at least one cell population in which apoptosis may be induced by activating RAR-&ggr; receptors. The invention further relates to the use of at least one RAR receptor agonist ligand, particularly 6-[3-(adamantan-1-yl)-4-(prop-2-ynyloxy)phenyl]naphthalene-2-carboxylic acid or 5-[(E)-3-oxo-3-(5,5,8,8-tetrahydronaphthalene-2-yl)propenyl]thiophene-2-carboxylic acid, as the active ingredient in a pharmaceutical or cosmetic composition and the use of such RAR agonist ligands to treat various disorders associated with apoptosis, differentiation, and proliferation. The compositions of the present invention may be used to prevent and/or control photo-induced or chronological aging of the skin.

  本发明涉及使用至少一种RAR受体激动剂配体，特别是6-[3-(孔雀石-1-基)-4-(丙-2-炔氧基)苯基]萘-2-羧酸或5-[(E)-3-氧代-3-(5,5,8,8-四氢萘-2-基)丙烯基]噻吩-2-羧酸，用于制备一种药物组合物，以增加至少一种细胞群体中凋亡速率，其中通过激活RAR-γ受体可以诱导凋亡。该组合物特别适用于治疗与至少一种细胞群体中凋亡速率不足相关的疾病或紊乱，其中通过激活RAR-γ受体可以诱导凋亡。该发明还涉及使用至少一种RAR受体激动剂配体，特别是6-[3-(孔雀石-1-基)-4-(丙-2-炔氧基)苯基]萘-2-羧酸或5-[(E)-3-氧代-3-(5,5,8,8-四氢萘-2-基)丙烯基]噻吩-2-羧酸，作为药用或化妆品组合物中的活性成分，以及使用这些RAR激动剂配体治疗与凋亡、分化和增殖相关的各种紊乱。本发明的组合物可用于预防和/或控制皮肤的光致老化或年代老化。
• Naphthyl or tetrahydronaphthyl-substituted naphthoic acid and derivatives
  申请人：SRI International

  公开号：US04454341A1

  公开（公告）日：1984-06-12

  Compounds of the formulas: ##STR1## where X is methyl, methoxy, chlorine, or hydrogen, Y and Y.sub.1 are fluorine or hydrogen, R is hydroxy, alkoxy with 0 or 1 hydroxy substituent, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl with 0 or 1 hydroxy substituent or aryl and R.sup.2 is alkyl with 0 or 1 hydroxy substituent or aryl with the proviso that when Y or Y.sup.1 is fluorine, the other Y or Y.sup.1 is hydrogen. These compounds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.

  化学式为##STR1##其中X为甲基，甲氧基，氯或氢，Y和Y.sub.1为氟或氢，R为羟基，具有0或1个羟基取代基的烷氧基，芳基氧基，或NR.sup.1 R.sup.2，其中R.sup.1为氢，具有0或1个羟基取代基的烷基或芳基，R.sup.2为具有0或1个羟基取代基的烷基或芳基，但当Y或Y.sup.1为氟时，另一个Y或Y.sup.1为氢。这些化合物可用作化学预防剂，用于抑制上皮细胞中的肿瘤促进和治疗非恶性皮肤疾病。
• RETINOID COMPOUNDS AND THEIR USE
  申请人：Przyborski Stefan

  公开号：US20100093088A1

  公开（公告）日：2010-04-15

  The invention relates to retinoid compounds of the formula (I): wherein V is a hydrophobic group; W is a non-polyenic linker; and X is a polar group comprising a hydrogen bond donor; or a salt thereof, and to the use of such compounds in the control of cell differentiation.

  本发明涉及公式（I）的视黄醇类化合物：其中，V是疏水基团；W是非多烯链连接剂；X是极性基团，包括一个氢键供体；或其盐，以及在细胞分化控制中使用此类化合物。
• Prevention of glucocorticoid-induced skin atrophy
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0266992A2

  公开（公告）日：1988-05-11

  The present invention is directed to the topical administra­tion of a retinoid-containing pharmaceutical composition for the prevention of glucocorticoid-induced skin atrophy.

  本发明涉及一种含维甲酸的药物组合物的局部用药，用于预防糖皮质激素引起的皮肤萎缩。
• Method for the treatment or prevention of intrinsically aged skin with retinoids
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0379367A2

  公开（公告）日：1990-07-25

  A method for the treatment or prevention of intrinsically aged skin by the topical administration of retinoids is described.

  本文介绍了一种通过局部使用维甲酸来治疗或预防内在老化皮肤的方法。