62932-92-7

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-1-(3,5-DIHYDROXYPHENYL)ETHANONE is used as a key reagent for the preparation of terbutaline analogs. Terbutaline is a medication used to treat asthma and chronic obstructive pulmonary disease (COPD). It functions as a bronchodilator, helping to relax and widen the airways, thereby improving breathing. The synthesis of terbutaline analogs can lead to the development of new and improved medications for respiratory conditions.
Additionally, due to its unique chemical structure, 2-BROMO-1-(3,5-DIHYDROXYPHENYL)ETHANONE may also have potential applications in other areas of the pharmaceutical industry, such as the synthesis of other therapeutic agents or as a building block for the development of novel drug candidates. However, further research and development would be required to explore these possibilities and fully understand the compound's potential applications.

Preparation

Also obtained by treatment of 3,5-dihydroxyace-tophenone with cupric bromide in boiling ethyl acetate for 2.5 h.

InChI:InChI=1/C8H7BrO3/c9-4-8(12)5-1-6(10)3-7(11)2-5/h1-3,10-11H,4H2

Upstream product

• 51863-60-6 3,5-dihydroxyacetophenone 
• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 

Downstream Products

• 79889-91-1 5-Benzo[d]imidazo[2,1-b]thiazol-2-yl-benzene-1,3-diol 
• 1361026-96-1 3α-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]octane 
• 1360460-75-8 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane 
• 1361026-95-0 3α-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane 
• 53144-56-2 (R)‐5‐(2‐(tert‐butylamino)‐1‐hydroxyethyl)benzene‐1,3‐diol hydrochloride 
• 23031-25-6 terbutaline 

Relevant academic research and scientific papers

Novel Aryl-Substituted Pyrimidones as Inhibitors of 3-Mercaptopyruvate Sulfurtransferase with Antiproliferative Efficacy in Colon Cancer

The enzyme 3-mercaptopyruvate sulfurtransferase (3-MST) is one of the more recently identified mammalian sources of H2S. A recent study identified several novel 3-MST inhibitors with micromolar potency. Among those, (2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one) or HMPSNE was found to be the most potent and selective. We now took the central core of this compound and modified the pyrimidone and the arylketone sides independently. A 63-compound library was synthesized; compounds were tested for H2S generation from recombinant 3-MST in vitro. Active compounds were subsequently tested to elucidate their potency and selectivity. Computer modeling studies have delineated some of the key structural features necessary for binding to the 3-MST's active site. Six novel 3-MST inhibitors were tested in cell-based assays: they exerted inhibitory effects in murine MC38 and CT26 colon cancer cell proliferation; the antiproliferative effect of the compound with the highest potency and best cell-based activity (1b) was also confirmed on the growth of MC38 tumors in mice.

Preparation method of terbutaline sulfate

The invention discloses a preparation method of terbutaline sulfate, wherein the method comprises the following steps: carrying out a bromination reaction on 3,5-dihydroxyacetophenone as a raw material by using a bromination reagent without hydroxyl protection, carrying out reduction and ring closing, carrying out a ring-opening reaction with tert-butylamine, and finally forming a salt with sulfuric acid to obtain terbutaline sulfate. According to the method, the defects of requirement of deprotection after hydroxyl protection, use of various high-risk highly toxic reagents, long reaction stepand low yield in the prior art are overcome.

Synthesis and biological evaluation of novel SIPI-7623 derivatives as farnesoid X receptor (FXR) antagonists

Most of reported steroidal FXR antagonists are restricted due to low potency. We described the design and synthesis of novel nonsteroidal scaffold SIPI-7623 derivatives as FXR antagonists. The most potent compound A-11 (IC50 = 7.8 ± 1.1 μM) showed better activity compared to SIPI-7623 (IC50 = 40.8 ± 1.7 μM) and guggulsterone (IC50 = 45.9 ± 1.1 μM). Docking of A-11 in FXR’s ligand-binding domain was also studied.

Preparation method for terbutaline hemisulfate

The invention discloses a preparation method for terbutaline hemisulfate. The method comprises the following steps: by adopting 3, 5-resacetophenone as a raw material, performing bromination reaction by directly using a bromination reagent without protecting hydroxide radical, then reducing carbanyl group; condensing with tert-butylamine, finally, forming salt with sulfuric acid, thereby obtaining terbutaline hemisulfate. The method can overcome the defects of deprotection after hydroxide radical protection, usage of various high-risk toxic reagents, long reaction steps and low yield in the present technology.

Preparation method of terbutaline sulphate

The invention relates to a preparation method of terbutaline sulphate. The technical problems that according to an existing preparation method of terbutaline sulphate, high-pressure hydrogenation and other high-risk operations, and lithium methide, azomethane and other high-risk reagents exist, and cost is high are solved through the preparation method. 3,5-resacetophenone serves as a raw material, and terbutaline sulphate is obtained through hydroxyl protection, the bromination reaction, carbonyl reduction, the condensation reaction and sulphating. The preparation method can be suitable for industrially-produced terbutaline sulphate.

COMPOUNDS USEFUL AS MODULATORS OF TRPM8

The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.

Structure-based design, synthesis and structure-activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein

Using structure-based optimization procedures on in silico hits, dibenzosuberyl- and benzoate substituted tropines were designed as ligands for acetylcholine-binding protein (AChBP). This protein is a homolog to the ligand binding domain of the nicotinic acetylcholine receptor (nAChR). Distinct SAR is observed between two AChBP species variants and between the α7 and α4β2 nAChR subtype. The AChBP species differences are indicative of a difference in accessibility of a ligand-inducible subpocket. Hereby, we have identified a region that can be scrutinized to achieve selectivity for nicotinic receptor subtypes.

Ultrasounds-assisted synthesis of highly functionalized acetophenone derivatives in heterogeneous catalysis

A fast, general, environmentally friendly, and facile method for preparation of highly functionalized acetophenone derivatives under ultrasound irradiation in heterogeneous catalysis is presented. The ultrasound enhanced a remarkable rate of acceleration for bromination, the reaction time decrease significantly, reaction conditions are milder, the consumed energy decreases considerably and the amount of used solvents was reduced. Consequently, the ultrasounds-assisted bromination reaction could be considered ecofriendly. In the most cases under ultrasound irradiation the yields are higher, in some cases substantially. A comparative study, ultrasounds-conventional conditions was done.

Nitric oxide donor β2-agonists: Furoxan derivatives containing the fenoterol moiety and related furazans

The structure of fenoterol, a β2-adrenoceptor agonist used in therapy, has been joined with furoxan NO-donor moieties to give new NO-donor β2-agonists. The furazan analogues, devoid of the property to release NO, were also synthesized for comparison. All the compounds retained β2-agonistic activity at micromolar or submicromolar concentration when tested on guinea pig tracheal rings precontracted with carbachol. Among the furoxan derivatives, the NO contribution to trachea relaxation was evident with product 15b at micromolar concentrations. All the new NO-donor hybrids were able to dilate rat aortic strips precontracted with phenylephrine. Both furoxan and furazan derivatives displayed antioxidant activity greater than that of fenoterol.

Discovery and structure-activity relationship of the first non-pep tide competitive human glucagon receptor antagonists

The first non-peptide competitive human glucagon receptor antagonist, 2-(benzimidazol-2ylthio)-l-(3,4-dihydroxyphenyl)-l-ethanone, NNC 92-1687 (2), is described. This antagonist has a binding affinity of 20 μM (ICso) and a functional Ki = 9.1 μM at the human glucagon receptor. A structure-activity relationship (SAR) was obtained on this compound, and the results show that only the benzimidazole part can be changed without complete loss of affinity. Analogues with tert-butyl or benzyloxy groups in the 5-position of the benzimidazole moiety were found to be equipotent or slightly more potent, all displaying binding affinities around 5-20 μM. Most of the changes to the catechol and the linker gave compounds without any affinity toward the human glucagon receptor. The 3-hydroxy group could, however, in the presence of a 4-hydroxy group be changed to a methoxy or a chloro group while retaining affinity.