7-methoxy-3,4-dihydronaphthalene-1-carbonitrile | 158365-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methoxy-3,4-dihydronaphthalene-1-carbonitrile
• CAS: 158365-53-8
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: IBAXOSUDTXPJSA-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±41.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-3,4-dihydronaphthalene-1-carbonitrile 在 palladium on activated charcoal 四(三苯基膦)钯 、 4-异丙基甲苯 、 C₆H₅N*HCl 、 溴 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 反应 11.0h， 生成 3-(3-氟-4-羟基苯基)-7-羟基萘-1-甲腈
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 锂丁酯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.75h， 生成 7-methoxy-3,4-dihydronaphthalene-1-carbonitrile
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m

文献信息

• Substituted phenyl naphthalenes as estrogenic agents
  申请人：Wyeth

  公开号：US20030181519A1

  公开（公告）日：2003-09-25

  This invention provides estrogen receptor modulators of formula I, having the structure 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 , are as defined in the specification, or a pharmaceutically acceptable salt thereof.

  这项发明提供了具有结构的式I的雌激素受体调节剂 1 其中 R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，R 7 ，R 8 ，R 9 和R 10 如规范中所定义，或其药用可接受盐。
• Process for the synthesis of 3-(3-fluoro-4-hydroxyphenyl)-7-hydroxynaphthonitrile
  申请人：Wu Yanzhong

  公开号：US20050054870A1

  公开（公告）日：2005-03-10

  A process for making a compound of formula I and intermediate compounds thereof, wherein R 1 is CN, F or Cl; R 2 is H or Br; and R 3 and R 4 are each independently H or F. The compounds of formula I are useful in the treatment of chronic inflammatory diseases, such as rheumatoid arthritis.

  一种制备公式I化合物及其中间体化合物的方法，其中R1为CN、F或Cl；R2为H或Br；R3和R4分别独立地为H或F。公式I化合物在治疗慢性炎症性疾病，如类风湿性关节炎方面具有用途。
• Synthesis of 2-tetralones via a novel 1,2-carbonyl transposition of 1-tetralones
  作者：David C Pryde、Steven S Henry、A.I Meyers

  DOI：10.1016/0040-4039(96)00522-9

  日期：1996.5

  Simple acidic hydrolysis of epoxyamides 4, derived from 1-tetralones, furnishes the corresponding 2-tetralones in good yield.

  衍生自1-四氢萘酮的环氧酰胺4的简单酸性水解可提供相应的2-四氢萘酮，收率很高。
• A high-affinity subtype-selective fluorescent probe for estrogen receptor β imaging in living cells
  作者：Zhiye Hu、Lu Yang、Wentao Ning、Chu Tang、Qiuyu Meng、Jie Zheng、Chune Dong、Hai-Bing Zhou

  DOI：10.1039/c8cc00483h

  日期：——

  Estrogen receptor β (ERβ) has recently been identified as a pharmaceutical target in hormone replacement therapy for breast cancers. However, the biological function of ERβ in disease progression remains unclear. A highly ERβ-selective fluorescent probe (FPNM) was discovered exhibiting nanomolar affinity for ERβ with an ERβ/ERα selectivity as high as 80, which allowed specific labeling of intracellular

  雌激素受体β（ERβ）最近已被确定为乳腺癌荷尔蒙替代疗法的药物靶标。然而，ERβ在疾病进展中的生物学功能仍不清楚。发现具有高ERβ选择性的荧光探针（FPNM）对ERβ表现出纳摩尔摩尔亲和力，其ERβ/ERα选择性高达80，可以对细胞内ERβ进行特异性标记。此外，首次通过FPNM染色直接观察到各种细胞生物环境（例如前列腺癌（DU-145）或三阴性乳腺癌（MDA-MB-231））中不同的ERβ动态。
• Preparation and Binding Affinity of New Porphyrin Host Molecule for Ubiquinone Analogues
  作者：Takashi Hayashi、Takashi Miyahara、Yasunori Aoyama、Masanori Nonoguchi、Hisanobu Ogoshi

  DOI：10.1246/cl.1994.1749

  日期：1994.9

  αααα-meso-Tetra(7-hydroxy-1-naphthyl)porphyrin (1) is prepared as a host molecule for ubiquinone analogue, 2,3,5,6-tetramethoxy-p-benzoquinone (2). The affinity and thermodynamic aspects in porphyrin 1- quinone 2 pairing were determined by titrimetric measurement of electronic absorption and fluorescence spectra. The binding constant of 1 for 2 at 298 K is obtained; Ka = 7.9 × 102 M−1 in toluene. The fashion of this porphyrin-quinone pairing was large different from that of previous host, αααα-meso-tetra(2-hydroxy-1-naphthyl)porphyrin (3), -quinone 2 pairing.

  ααα-介-四(7-羟基-1-萘基)卟啉(1)是作为泛醌类似物--2,3,5,6-四甲氧基对苯醌(2)的宿主分子制备的。通过滴定法测量电子吸收光谱和荧光光谱，确定了卟啉-1-醌-2 配对的亲和力和热力学方面。结果表明，在 298 K 时，1 与 2 的结合常数为 Ka = 7.9 × 102 M-1（甲苯）。这种卟啉-醌配对的方式与以前的宿主--ααα-介-四（2-羟基-1-萘基）卟啉（3）-醌 2 配对的方式有很大不同。