588-63-6

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Phenoxypropyl bromide is used as a reagent for the synthesis of damidines, which are compounds studied in the context of myotonic dystrophy. Myotonic dystrophy is a genetic disorder characterized by muscle weakness and myotonia, and the development of effective treatments is crucial for managing the condition.
Additionally, 3-Phenoxypropyl bromide is used in the preparation of phenoxyalkylbenzimidazoles, which exhibit antitubercular activity. Tuberculosis is a bacterial infection that primarily affects the lungs and is a significant global health concern. The development of new antitubercular agents is essential for combating drug-resistant strains and improving treatment outcomes.

InChI:InChI=1/C9H11BrO/c10-7-4-8-11-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

Upstream product

• 139-02-6 sodium phenoxide 
• 109-64-8 1,3-dibromo-propane 
• 108-95-2 phenol 
• 27983-04-6 1-(3-bromopropoxy)-4-chlorobenzene 
• 32599-03-4 1-(3-phenoxypropyl)piperidine 
• 506-68-3 bromocyane 
• 3229-70-7 phenolate 
• 627-18-9 1-bromo-3-propanol 
• 6180-61-6 3-phenoxypropanol 
• 66003-76-7 Diphenyliodonium triflate 
• 6303-58-8 4-phenyloxybutanoic acid 
• 2364-59-2 γ-phenoxybutyric acid ethyl ester 
• 57334-32-4 3-phenoxypropyl-4-methylbenzene sulfonate 
• 1746-13-0 allyl phenyl ether 

Downstream Products

• 32599-03-4 1-(3-phenoxypropyl)piperidine 
• 6265-68-5 1,4-bis-(3-phenoxy-propyl)-piperazine 
• 113649-31-3 1-(3-phenoxy-propyl)-4-phenyl-piperidine-4-carboxylic acid ethyl ester 
• 67746-99-0 isobutyl-(3-phenoxy-propyl)-amine 
• 854879-95-1 2-(3-phenoxy-propyl)-acetoacetic acid ethyl ester 
• 861338-42-3 Trimethylenglykol-phenylaether-(2-oxy-phenylaether) 
• 160408-06-0 ethyl-(3-phenoxy-propyl)-amine 
• 627040-32-8 (3-phenoxy-propyl)-dipropyl-amine 
• 116871-21-7 N-(3-phenoxypropyl)-N-butylbutan-1-amine 
• 55247-45-5 (3-phenoxy-propyl)-propyl-amine 
• 873963-56-5 bis-(3-phenoxy-propyl)-malonic acid diethyl ester 
• 61372-56-3 1-methoxy-3-phenoxy-propane 

Relevant academic research and scientific papers

Preparation method 3 - phenoxybromopropane or analogue thereof

The invention discloses a preparation method of 3 -phenoxybromopropane or an analogue thereof, wherein 3 - phenoxybromopropane and an allyl compound thereof are obtained through substitution reaction and addition reaction so as to avoid the inconvenience of using gaseous hydrogen bromide, 2nd-step addition reaction is realized by using the brominated salt and the acid in situ, and the process is simple in operation. The condition is easy to control, the atom economy is good, the aspect of environmental impact is low pollution, zero emission accords with the current green chemical synthesis direction, and the cost is economic.

Study of the structure-bioactivity of fleximers: synthesis, crystal structure, Hirshfeld surface analysis, and anti-inflammatory assays

Synthesized and natural pyridones/pyridines derivatives exhibiting diverse biological activities. 2-pyridone has lactam-lactim tautomerization like thymine and uracil bases. In this study, COX-2 target based series of pyridone/pyridine linked fleximers were designed, synthesized and studied. All analogues binding affinity with COX-2 active site were studied through molecular docking, and anti-inflammatory activity studied by in vivo analysis. Weak interactions were studied to find binding sites among analogues through crystal packing, Hirshfeld surface analysis and in silico analysis. All the analogues exhibited anti-inflammatory activity, while compound (3) is the most active analogue among the series. In contrast, since compound (3) is a pyridine-phthalimide ring-containing analogue, the presence of a phthalimide group probably favors anti-inflammatory activity over other types of rings. The results suggested further investigations on compounds as anti-inflammatory prodrugs.

Development of Membrane-Active Honokiol/Magnolol Amphiphiles as Potent Antibacterial Agents against Methicillin-Resistant Staphylococcus aureus (MRSA)

Currently, infections caused by drug-resistant bacteria have become a new challenge in anti-infective treatment, seriously endangering public health. In our continuous effort to develop new antimicrobials, a series of novel honokiol/magnolol amphiphiles were prepared by mimicking the chemical structures and antibacterial properties of cationic antimicrobial peptides. Among them, compound 5i showed excellent antibacterial activity against Gram-positive bacteria and clinical MRSA isolates (minimum inhibitory concentrations (MICs) = 0.5-2 μg/mL) with low hemolytic and cytotoxic activities and high membrane selectivity. Moreover, 5i exhibited rapid bactericidal properties, low resistance frequency, and good capabilities of disrupting bacterial biofilms. Mechanism studies revealed that 5i destroyed bacterial cell membranes, resulting in bacterial death. Additionally, 5i displayed high biosafety and potent in vivo anti-infective potency in a murine sepsis model. Our study indicates that these honokiol/magnolol amphiphiles shed light on developing novel antibacterial agents, and 5i is a potential antibacterial candidate for combating MRSA infections.

Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate

Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- A nd nine-membered benzolactams.

Preparation method of high-purity 3-phenoxypropyl bromide

The invention discloses a preparation method of aclidinium bromide key intermediate 3-phenoxypropyl bromide (formula I). The method comprises the following steps: by taking phenol and halogenated propanol as raw materials, carrying out nucleophilic substitution reaction under an alkaline condition to generate 3-phenoxy propanol, then reacting with a sulfonic acid esterification reagent to generateactive ester of 3-phenoxy propanol, refining the ester, and then reacting with a bromide of an alkali metal to generate 3-phenoxypropyl bromide. The preparation method provided by the invention has the advantages of cheap and easily available raw materials, simple operation, mild reaction conditions, no harsh reaction conditions, and high yield and purity of the obtained product, and is suitablefor industrial production.

Indolyl Azaspiroketal Mannich Bases Are Potent Antimycobacterial Agents with Selective Membrane Permeabilizing Effects and in Vivo Activity

The inclusion of an azaspiroketal Mannich base in the membrane targeting antitubercular 6-methoxy-1-n-octyl-1H-indole scaffold resulted in analogs with improved selectivity and submicromolar activity against Mycobacterium tuberculosis H37Rv. The potency enhancing properties of the spiro-fused ring motif was affirmed by SAR and validated in a mouse model of tuberculosis. As expected for membrane inserting agents, the indolyl azaspiroketal Mannich bases perturbed phospholipid vesicles, permeabilized bacterial cells, and induced the mycobacterial cell envelope stress reporter promoter piniBAC. Surprisingly, their membrane disruptive effects did not appear to be associated with bacterial membrane depolarization. This profile was not uniquely associated with azaspiroketal Mannich bases but was characteristic of indolyl Mannich bases as a class. Whereas resistant mycobacteria could not be isolated for a less potent indolyl Mannich base, the more potent azaspiroketal analog displayed low spontaneous resistance mutation frequency of 10-8/CFU. This may indicate involvement of an additional envelope-related target in its mechanism of action.

Design, synthesis, and biological evaluation of novel pan agonists of FFA1, PPARγ and PPARδ

The free fatty acid receptor 1 (FFA1) and peroxisome proliferator-activated receptors (PPARs) have attracted interest as potent targets for the treatment of metabolic syndrome such as type 2 diabetes. Based on the hypothesis that the dual agonists of PPARs and FFA1 would act as insulin sensitizers and secretagogues by simultaneous activation of PPARs and FFA1, we developed the design strategy to obtain dual PPARs/FFA1 agonist by hybrid FFA1 agonist 1 with PPARδ agonist 2 in consideration of their structural similarity. As expected, systematic exploration of structure-activity relationship and molecular modeling, results in the discovery of lead compound 15, a pan agonist with relative balanced activities between FFA1, PPARγ and PPARδ. The dose-response relationship studies suggested that the pan agonist 15 suppressed the excursion of blood glucose levels in a dose-dependent manner. During a 5-days treatment in ob/ob mice, the pan agonist 15 (100 mg/kg) revealed sustained hypoglycemic effect, even proximity to the most advanced FFA1 agonist (TAK-875, 40 mg/kg), which might be attributed to its pan PPARs/FFA1 activities to simultaneous regulate the mechanism of insulin secretion and resistance. These positive results suggest that the dual PPARs/FFA1 agonists such as lead compound 15 might be novel therapeutic strategy to modulate the complex pathological mechanisms of type 2 diabetes.

Discovery and structure-activity relationship studies of N-substituted indole derivatives as novel Mcl-1 inhibitors

Myeloid cell leukemia-1 (Mcl-1) is an important antiapoptotic protein functioning through protein-protein interactions. We discovered LSL-A6 (2-((2-carbamoyl-1-(3-(4-methoxyphenoxy)propyl)-1H-indol-6-yl)oxy)acetic acid) with a novel N-substituted indole scaffold to interfere Mcl-1 binding as a novel Mcl-1 inhibitor. Molecular modeling indicated that this compound binds with Mcl-1 by interaction with P2 and R263 hot-spots. Structure modification focused on several moieties including indole core, hydrophobic tail and acidic chain were conducted and structure-activity relationship was analyzed. The most potent compound 24d which exhibited Ki value of 110?nM for interfering Mcl-1 binding was obtained after hit-to-lead modification.

Design, Synthesis, and Biological Evaluation of Coupled Bioactive Scaffolds as Potential Anticancer Agents for Dual Targeting of Dihydrofolate Reductase and Thioredoxin Reductase

The dihydrofolate reductase (DHFR) and thioredoxin reductase (TrxR) enzymes are involved in the process of tumor cell growth and survival. The 4,6-diamino-1,2-dihydro-1,3,5-triazine scaffold is well-established as a useful scaffold for DHFR inhibition, while chalcones have been reported to be inhibitors of TrxR. In this study, 15 novel compounds designed by the structural combination of the 4,6-diamino-1,2-dihydro-1,3,5-triazine and chalcone scaffolds via a diether linker were successfully synthesized and characterized. All of the compounds demonstrated dual inhibition against DHFR and TrxR when they were assessed by in vitro enzyme assays. The compounds also exhibited antiproliferative activity against the MCF-7 and HCT116 cells. The more potent analogs 14 and 15 were found to inhibit cellular DHFR and TrxR activities in HCT116 cells. Therefore, this study provided compelling evidence that 14 and 15 could exert their anticancer property via multitarget inhibition at the cellular level.

LSD1 Inhibitors

The present invention relates to compounds that inhibit LSD1 activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.