6-bromo-1,2-dimethoxynaphthalene | 65249-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-1,2-dimethoxynaphthalene
• CAS: 65249-23-2
• 化学式: C₁₂H₁₁BrO₂
• 分子量: 267.122
• InChiKey: HBHNSGZFMPZMCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  6-bromo-1,2-dimethoxynaphthalene 在 乙酸酐 、 铁粉 、 copper(II) nitrate 、 溶剂黄146 、 三乙胺 作用下， 以 水 为溶剂， 反应 8.0h， 生成 2-[5-[(7-bromo-3,4-dimethoxynaphthalen-1-yl)amino]pentan-2-yl]isoindole-1,3-dione
  参考文献：
  名称：

  4-[(Aminoalkyl)amino]-1,2-dimethoxynaphthalenes as antimalarial agents

  摘要：

  A series of 4-[N-(aminoalkyl)amino]-1,2-dimethoxynaphthalenes was prepared and tested for radical curative activity in rhesus monkeys infected with P. cynomolgi. Some radical curative activity was observed.

  DOI：

  10.1021/jm00179a009
• 作为产物：
  描述：

  1-benzoyloxy-6-bromo-[2]naphthol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 生成 6-bromo-1,2-dimethoxynaphthalene
  参考文献：
  名称：

  Ansari, M. Aslam; Mathur, K. B. L.; Ahluwalia, V. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 587 - 589

  摘要：

  DOI：

文献信息

• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors
  作者：Nobuyuki Matsunaga、Tomohiro Kaku、Akio Ojida、Toshimasa Tanaka、Takahito Hara、Masuo Yamaoka、Masami Kusaka、Akihiro Tasaka

  DOI：10.1016/j.bmc.2004.06.016

  日期：2004.8

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.
• Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck
  作者：Terrence R. Burke、Benjamin Lim、Victor E. Marquez、Zhen Hong Li、Joseph B. Bolen、Irena Stefanova、Ivan D. Horak

  DOI：10.1021/jm00056a001

  日期：1993.2

  A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 muM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 muM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.
• An Efficient Synthesis of 5,6-Dimethoxy 1- and 2-Naphthols<i>via</i>Teuber Reaction
  作者：Jia-hua Cui、Shao-shun Li

  DOI：10.1002/jccs.201300065

  日期：2013.9

  AbstractBased on the oxidation of 1,5‐naphthalenediol (4) and 6‐bromo‐2‐naphthol (9) via Teuber reaction, an efficient synthesis of 5,6‐dimethoxy‐1‐naphthol (1) and 5,6‐dimethoxy‐2‐naphthol (2) was achieved with high overall yield (16% for 1 and 25% for 2). The key steps of the synthetic strategy involved the oxidation of naphthols (4 and 9) to the corresponding naphthoquinones (5 and 10) and the conversion of 5,6‐dimethoxy‐2‐naphthaldehyde to 5,6‐dimethoxy‐2‐naphthol formate through Baeyer‐Villiger oxidation‐rearrangement.
• New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent
  作者：Cédric Maurin、Cédric Lion、Fabrice Bailly、Nadia Touati、Hervé Vezin、Gladys Mbemba、Jean François Mouscadet、Zeger Debyser、Myriam Witvrouw、Philippe Cotelle

  DOI：10.1016/j.bmc.2010.05.059

  日期：2010.7

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.