3-Bromobenzyl bromide
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3-Bromobenzyl bromide

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3-Bromobenzyl bromide (CAS# 823-78-9) is a useful research chemical.

Category
Others
Catalog number
BAT-002377
CAS number
823-78-9
Molecular Formula
C7H6Br2
Molecular Weight
249.94
3-Bromobenzyl bromide
IUPAC Name
1-bromo-3-(bromomethyl)benzene
Synonyms
m-Bromobenzyl bromide
Appearance
White crystal
Purity
≥ 99 %
Density
1.56 g/cm3
Melting Point
40-42 ℃
Boiling Point
128-130 ℃
Storage
Store at RT
InChI
InChI=1S/C7H6Br2/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2
InChI Key
ZPCJPJQUVRIILS-UHFFFAOYSA-N
Canonical SMILES
C1=CC(=CC(=C1)Br)CBr
1. The evaluation of prophylactic efficacy of newly developed reversible inhibitors of acetylcholinesterase in soman-poisoned mice - a comparison with commonly used pyridostigmine
Jiri Kassa, Jan Korabecny, Vendula Sepsova, Martina Tumova Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):571-6. doi: 10.1111/bcpt.12269. Epub 2014 Jun 6.
The ability of four newly developed reversible inhibitors of acetylcholinesterase (PC-37, PC-48, JaKo 39, JaKo 40) and currently available carbamate pyridostigmine to increase the resistance of mice against soman and the efficacy of antidotal treatment of soman-poisoned mice was evaluated and compared. No reversible inhibitor of acetylcholinesterase studied was able to decrease the LD50 value of soman in mice. Thus, the pharmacological pre-treatment with pyridostigmine or newly synthesized inhibitors of acetylcholinesterase was not able to significantly protect mice against soman-induced lethal acute toxicity. In addition, neither pyridostigmine nor new reversible inhibitors of acetylcholinesterase was able to increase the efficacy of antidotal treatment (the oxime HI-6 in combination with atropine) of soman-poisoned mice. These findings demonstrate that pharmacological pre-treatment of soman-poisoned mice with tested reversible inhibitors of acetylcholinesterase is not promising.
2. The diazo route to diazonamide A. Studies on the indole bis-oxazole fragment
James R Davies, Peter D Kane, Christopher J Moody J Org Chem. 2005 Sep 2;70(18):7305-16. doi: 10.1021/jo0509760.
[structure: see text] Various approaches to the indole bis-oxazole fragment of the marine secondary metabolite diazonamide A are described, all of which feature dirhodium(II)-catalyzed reactions of diazocarbonyl compounds in key steps. Thus, 3-bromophenylacetaldehyde is converted into an alpha-diazo-beta-ketoester, dirhodium(II)-catalyzed reaction of which with N-Boc-valinamide resulted in N-H insertion of the intermediate rhodium carbene to give a ketoamide that readily underwent cyclodehydration to give (S)-2-(1-tert-butoxycarbonylamino)-2-methylpropyl]-5-(3-bromobenzyl)oxazole-4-carboxamide, after ammonolysis of the initially formed ester. This aryl bromide was then coupled to a 3-formyl-indole-4-boronate under Pd catalysis to give the expected biaryl. Subsequent conversion of the aldehyde group into a second alpha-diazo-beta-ketoester gave a substrate for an intramolecular carbene N-H insertion, although attempts to effect this cyclization were unsuccessful. A second approach to an indole bis-oxazole involved an intermolecular rhodium carbene N-H insertion, followed by oxazole formation to give (S)-2-[1-tert-(butoxycarbonylamino)-2-methylpropyl]-5-methyloxazole-4-carboxamide. A further N-H insertion of this carboxmide with the rhodium carbene derived from ethyl 2-diazo-3-[1-(2-nitrobenzenesulfonyl)indol-3-yl]-3-oxopropanoate gave a ketoamide, cyclodehydration of which gave the desired indole bis-oxazole. Finally, the boronate formed from 4-bromotryptamine was coupled to another diazocarbonyl-derived oxazole to give the corresponding biaryl, deprotection and cyclization of which produced a macrocyclic indole-oxazole derivative. Subsequent oxidation and cyclodehydration incorporated the second oxazole and gave the macrocyclic indole bis-oxazole.
3. Design, synthesis and biological assessment of new 1-benzyl-4-((4-oxoquinazolin-3(4 H)-yl)methyl) pyridin-1-ium derivatives (BOPs) as potential dual inhibitors of acetylcholinesterase and butyrylcholinesterase
Samaneh Zarei, Mohammad Shafiei, Maryam Firouzi, Loghman Firoozpour, Kouros Divsalar, Ali Asadipour, Tahmineh Akbarzadeh, Alireza Foroumadi Heliyon. 2021 Apr 8;7(4):e06683. doi: 10.1016/j.heliyon.2021.e06683. eCollection 2021 Apr.
Alzheimer's disease (AD), is among the most growing neurodegenerative diseases, which is mainly caused by the acetylcholine neurotransmitter loss in the hippocampus and cortex. Emerging of the dual Acetylcholinesterase (AChE)/Butyrylcholinesterase (BuChE) inhibitors has increased for treating Alzheimer disease. In this study, we would like to report the design and synthesis of a new sequence of 1-benzyl-4-((4-oxoquinazolin-3(4H)-yl)methyl) pyridin-1-ium derivatives (BOPs) assessed as BuChE and AChE inhibitors. Ellman's approach was used for the evaluation of AChE and BuChE inhibitory activities. Moreover, docking research was conducted to predict the action mechanism. Among all synthesized compounds, 1-(3-bromobenzyl)-3-((4-oxoquinazolin-3(4H)-yl)methyl) pyridin-1-ium bromide (BOP-1) was found to be the most active compound with dual activity for inhibition of AChE (IC50 = 5.90 ± 0.07μM), and BuChE (IC50 = 6.76 ± 0.04μM) and 1-(4-chlorobenzyl)-3-((6,7-dimethoxy-4-oxoquinazolin-3(4H)-yl)methyl) pyridin-1-ium chloride (BOP-8) showed the highest AChE inhibitory activity (IC50s = 1.11 ± 0.09 μM). The synthesized compounds BOP-1 and BOP-8 could be proposed as valuable lead compounds for further drug discovery development against AD.
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