1-bromo-7-bromomethylnaphthalene | 98331-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-7-bromomethylnaphthalene
• 英文别名: 8-bromo-2-(bromomethyl)naphthalene；1-Bromo-7-(bromomethyl)naphthalene
• CAS: 98331-27-2
• 化学式: C₁₁H₈Br₂
• 分子量: 299.993
• InChiKey: ZHUIAQBJTUKDST-UHFFFAOYSA-N

物化性质

• 熔点：
  112-116 °C
• 沸点：
  363.3±17.0 °C(Predicted)
• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-7-bromomethylnaphthalene 在 三乙基硅烷 、 2-硝基丙烷 、 sodium ethanolate 、 乙基氯化镁 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 90.0h， 生成 4-[(8-bromo-2-naphthyl)methyl]-3-isopropoxy-5-(1-methoxycarbonyl-4-piperidyl)isoxazol
  参考文献：
  名称：

  Potent 4-Aryl- or 4-Arylalkyl-Substituted 3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Molecular Modeling

  摘要：

  We have previously described a series of competitive GABA(A) antagonists derived from the low-efficacy partial agonist 5-(4-piperidyl)-3-isoxazolol (4-PIOL, 4). The 2-naphthylmethyl analogue, 4-(2-naphthylmethyl)-5-(4-piperidyl)-3-isoxazolol (5), provided affinity for the GABA(A) receptor site higher than that of the standard GABA(A) receptor antagonist, SR 95531 (3). Molecular modeling studies of these compounds exposed a cavity at the receptor recognition site capable of accommodating aromatic groups of substantial size in the 4-position in the 3-isoxazolol ring, Here we present a series of analogues of 5, with various substituents in different positions in the naphthyl ring system (6a-k), and compounds with aromatic substituents directly attached to the 4-position of the 3-isoxazolol ring (7l-n). The compounds have been pharmacologically characterized using receptor-binding assays and electrophysiological whole-cell patch-clamp techniques. All of the tested compounds show affinity for the GABA(A) receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (K-i = 45, 109, and 80 nM, respectively) comparable with that of 5 (Ki 49 nM), the 1-bromo analogue, 6a, provided the highest receptor affinity of the series (Ki 10 nM). Introduction of a series of different substituents in the 1-position in the 2-naphthyl ring system led to compounds. 6,e-k. with retained high affinity for the GABA(A) receptor (K-i = 16-250 nM). Introduction of a phenyl ring directly into the 4-position on the 3-isoxazolol ring gave a 41-fold increase in affinity relative to that of 4-PIOL. In whole-cell patch-clamp recordings from cultured cerebral cortical neurons. all of the tested compounds were able to inhibit the effect of the Specific GABA(A) agonist, isoguvacine, 6a showing antagonist potency (IC50 = 42 nM) markedly higher than that, of 3 (IC50 = 240 nM). Molecular modeling studies, based on the compounds described, emphasized the importance of the distal ring in 5 for receptor affinity and the considerable dimensions of the proposed receptor cavity. Furthermore, the phenyl rings in 71 and in 6k were shown to represent highly favorable positions for an aromatic ring in previously unexplored receptor regions in terms of a pharmacophore model.

  DOI：

  10.1021/jm049256w
• 作为产物：
  描述：

  2-溴苯乙酰氯 在 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 三苯基甲醇 、 偶氮二异丁腈 、 四氯化钛 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 50.75h， 生成 1-bromo-7-bromomethylnaphthalene
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006

文献信息

• Novel naphthalenylalkyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as
  申请人：American Home Products Corporation

  公开号：US04897405A1

  公开（公告）日：1990-01-30

  This invention relates to novel [(substituted naphthalenyl)alkyl]-3H-1,2,3,5-oxathiadiazole 2-oxides, to the processes for their preparation, to methods for using the compounds, and to pharmaceutical compositions thereof. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  这项发明涉及新型[(取代萘基)烷基]-3H-1,2,3,5-噻二唑二氧化物，以及它们的制备方法、化合物的使用方法和相关的药物组合物。这些化合物具有药理特性，使它们对于治疗糖尿病及相关疾病有益。
• Processes for the preparation of novel
  申请人：American Home Product

  公开号：US04966975A1

  公开（公告）日：1990-10-30

  This invention relates to the processes for the production of novel [(substituted naphthalenyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxides. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  这项发明涉及生产新型[(取代萘基)甲基]-3H-1,2,3,5-噻二唑-2-氧化物的过程。这些化合物具有药理特性，使它们对治疗糖尿病及相关疾病有益。
• Naphthalene derivatives
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0393941A1

  公开（公告）日：1990-10-24

  This invention relates to novel [(substituted naphthalenyl)alkyl]-3H-1,2,3,5-oxathiadiazole 2-oxides of formula wherein n is 0 to 4 and R¹ and R² have specified meanings, and their salts. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  本发明涉及新型[(取代的萘基)烷基]-3H-1,2,3,5-噁二唑 2-氧化物，其式为 其中 n 为 0 至 4，R¹ 和 R² 具有特定含义，以及它们的盐类。这些化合物具有药物特性，有利于治疗糖尿病及相关疾病。
• Duchene, Karl-Heinz; Voegtle, Fritz, Angewandte Chemie, 1985, vol. 97, # 10, p. 866
  作者：Duchene, Karl-Heinz、Voegtle, Fritz

  DOI：——

  日期：——
• ALESSI, THOMAS R.;DOLAK, TERENCE M.;ELLINGBOE, JOHN W.;LOMBARDO, LOUIS J.
  作者：ALESSI, THOMAS R.、DOLAK, TERENCE M.、ELLINGBOE, JOHN W.、LOMBARDO, LOUIS J.

  DOI：——

  日期：——