98331-27-2

Basic information

• Product Name: 8-bromo-2-(bromomethyl)naphthalene
• Synonyms: 8-bromo-2-(bromomethyl)naphthalene
• CAS NO: 98331-27-2
• Molecular Formula: C₁₁H₈Br₂
• Molecular Weight: 299.98922
• Mol File: 98331-27-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 8-bromo-2-(bromomethyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 8-bromo-2-(bromomethyl)naphthalene(98331-27-2)
• EPA Substance Registry System: 8-bromo-2-(bromomethyl)naphthalene(98331-27-2)

Safety Data

• Hazardous Substances Data: 98331-27-2(Hazardous Substances Data)

Upstream product

• 7511-27-5 1-bromo-7-methylnaphthalene 
• 127810-66-6 8-bromo-2-hydroxy-2-methyl-1,2,3,4-tetrahydronaphthalene 
• 117294-21-0 8-bromo-2-tetralone 
• 55116-09-1 2-bromophenylacetyl chloride 
• 18698-97-0 ortho-bromophenylacetic acid 

Downstream Products

• 841259-41-4 8-bromonaphthalene-2-carbaldehyde 
• 98331-28-3 7-Methoxymethyl-1-(3-methoxymethyl-phenoxy)-naphthalene 
• 98331-29-4 7-Bromomethyl-1-(3-bromomethyl-phenoxy)-naphthalene 

Relevant articles and documents

Potent 4-aryl- or 4-arylalkyl-substituted 3-isoxazolol GABAA antagonists: Synthesis, pharmacology, and molecular modeling

We have previously described a series of competitive GABAA 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 GABAA receptor site higher than that of the standard GABAA 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 (71-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 GABAA receptor site. While the 5-, 7-, and 8-bromo analogues, 6b-d, showed receptor affinities (Ki = 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, 6c-k, with retained high affinity for the GABA A receptor (Ki = 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 GABAA 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.

Novel naphthalenylalkyl-3H-1,2,3,5-oxathiadiazole 2-oxides useful as antihyperglycemic agents

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

Das erste Phan: Ein neues helicales Molekuelgeruest

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