568544-04-7

Basic information

• Product Name: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE
• Synonyms: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE
• CAS NO: 568544-04-7
• Molecular Formula: C₉H₆BrClN₂O
• Molecular Weight: 273.51
• Mol File: 568544-04-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(568544-04-7)
• EPA Substance Registry System: 2-(4-BROMO-PHENYL)-5-CHLOROMETHYL-[1,3,4]OXADIAZOLE(568544-04-7)

Safety Data

• Hazardous Substances Data: 568544-04-7(Hazardous Substances Data)

Usage

General Description

2-(4-Bromo-phenyl)-5-chloromethyl-[1,3,4]oxadiazole, also known as BPOX, is a chemical compound with a molecular formula C9H6BrClN2O. It is a heterocyclic compound containing an oxadiazole ring, as well as bromine and chlorine substituents. BPOX has shown potential as a building block in the synthesis of pharmaceutical compounds and agrochemicals, due to its diverse reactivity and ability to participate in various chemical reactions. It also exhibits interesting biological activities, including anti-inflammatory and antitumor properties, which make it a promising candidate for drug development. BPOX is mainly used in research and development in the pharmaceutical and agrochemical industries.

Upstream product

• 199938-23-3 4-bromo-N’-(chloroacetyl)benzohydrazide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 5933-32-4 4-bromobenzoic acid hydrazide 
• 79-11-8 chloroacetic acid 
• 5798-75-4 Ethyl 4-bromobenzoate 

Downstream Products

• 911061-96-6 2-(4-bromophenyl)-5-(methoxymethyl)-1,3,4-oxadiazole 
• 871583-85-6 2-({[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methoxy}methyl)-4-methoxyaniline 
• 871583-96-9 benzyl{[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methyl}[(6-methoxy-3-nitropyridin-2-yl)methyl]amine 
• 1250479-78-7 2-(azidomethyl)-5-(4-bromophenyl)-1,3,4-oxadiazole 
• 1279822-43-3 tert-butyl N-[[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methyl]carbamate 
• 1453855-93-0 1-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-N,N-dimethylmethanamine 
• 911062-10-7 3-(4-bromophenyl)-4-(4-methoxyphenyl)-5-(1H-pyrazol-1-ylmethyl)-4H-1,2,4-triazole 
• 911062-06-1 5-[3-(4-bromophenyl)-5-(methoxymethyl)-4H-1,2,4-triazol-4-yl]-2-methoxypyridine 
• 871583-86-7 1-(4-bromophenyl)-8-methoxy-4H,6H-[1,2,4]triazolo[4,3-a][4,1]benzoxazepine 

Relevant articles and documents

Oxazole ring-containing honokiol thioether derivative and preparation method and application thereof

The invention discloses an oxazole ring-containing honokiol thioether derivative, a preparation method thereof and application of the oxazole ring-containing honokiol thioether derivative as an alpha-glucosidase inhibitor, the chemical structure of the oxazole ring-containing honokiol thioether derivative is shown as a general formula (I), and R is selected from non-substituted or substituted phenyl. Compared with the prior art, the invention provides the novel honokiol thioether derivative containing the oxazole ring, and the honokiol thioether derivative containing the oxazole ring has good inhibitory activity on alpha-glucosidase, provides more possibilities for treating diabetes, and is expected to be used for preparing novel candidate drug molecules for treating diabetes. In addition, the preparation process is simple, the cost is low, and the yield is high.

Synthesis and biological evaluation of honokiol derivatives bearing 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3h)-ones as potential viral entry inhibitors against sars-cov-2

The 2019 coronavirus disease (COVID-19) caused by SARS-CoV-2 virus infection has posed a serious danger to global health and the economy. However, SARS-CoV-2 medications that are specific and effective are still being developed. Honokiol is a bioactive component from Magnoliae officinalis Cortex with damp-drying effect. To develop new potent antiviral molecules, a series of novel honokiol analogues were synthesized by introducing various 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)oxazol-2(3H)-ones to its molecule. In a SARS-CoV-2 pseudovirus model, all honokiol derivatives were examined for their antiviral entry activities. As a result, 6a and 6p demonstrated antiviral entry effect with IC50 values of 29.23 and 9.82 μM, respectively. However, the parental honokiol had a very weak antiviral activity with an IC50 value more than 50 μM. A biolayer interfero-metry (BLI) binding assay and molecular docking study revealed that 6p binds to human ACE2 protein with higher binding affinity and lower binding energy than the parental honokiol. A competitive ELISA assay confirmed the inhibitory effect of 6p on SARS-CoV-2 spike RBD’s binding with ACE2. Importantly, 6a and 6p (TC50 > 100 μM) also had higher biological safety for host cells than honokiol (TC50 of 48.23 μM). This research may contribute to the discovery of potential viral entrance inhibitors for the SARS-CoV-2 virus, although 6p’s antiviral efficacy needs to be validated on SARS-CoV-2 viral strains in a biosafety level 3 facility.

One-potCuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4/1,2,4-oxadiazoles starting from available chloromethyl-1,3,4/1,2,4-oxadiazoles

The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “cli

Design and synthesis of new norfloxacin-1,3,4-oxadiazole hybrids as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

Toward the search of new antibacterial agents to control methicillin-resistant Staphylococcus aureus (MRSA), a class of new norfloxacin-1,3,4-oxadiazole hybrids were designed and synthesized. Antibacterial activities against drug-sensitive bacteria S. aureus and clinical drug resistant isolates of MRSA were evaluated. Compound 5k exhibited excellent antibacterial activities against S. aureus (MIC: 2 μg/mL) and MRSA1–3 (MIC: 0.25–1 μg/mL). The time-kill kinetics demonstrated that compound 5k had an advantage over commonly used antibiotics vancomycin in killing S. aureus and MRSA. Moreover, compound 5k could inhibit the bacteria and destroy their membranes in a short time, and showed very low cytotoxicity to NRK-52E cells. Some interesting structure-activity relationships (SARs) were also discussed. These results indicated that these norfloxacin-1,3,4-oxadiazole hybrids could be further developed into new antibacterial agents against MRSA.

Design, synthesis, evaluation, and molecular docking of ursolic acid derivatives containing a nitrogen heterocycle as anti-inflammatory agents

Ursolic acid derivatives containing oxadiazole, triazolone, and piperazine moieties were synthesized in an attempt to develop potent anti-inflammatory agents. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, and HRMS. Most of the synthesized compounds showed pronounced anti-inflammatory effects at 100 mg/kg. In particular, compound 11b, which displayed the most potent anti-inflammatory activity of all of the compounds prepared, with 69.76% inhibition after intraperitoneal administration, was more potent than the reference drugs indomethacin and ibuprofen. The cytotoxicity of the compounds was also assessed by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay, and no compounds showed any appreciable cytotoxic activity (IC50 >100 μmol/L). Furthermore, molecular docking studies of the synthesized compounds were performed to rationalize the obtained biological results. Overall, the results indicate that compound 11b could be a therapeutic candidate for the treatment of inflammation.

Conjugated oligo-aromatic compounds bearing a 3,4,5-trimethoxy moiety: Investigation of their antioxidant activity correlated with a DFT Study

A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were

Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety

A series of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety were designed, synthesized and evaluated for their in vitro antitumor activities against SMMC-7721, MCF-7 and A549 human tumor cell lines by CCK-8 assay. The bioassay results demonstrated that most of the tested compounds showed potent antitumor activities, and some compounds exhibited stronger effects than positive control 5-fluorouracil (5-FU) against various cell lines. Among these compounds, compound 8d showed the best inhibitory effect against SMMC-7721 cells, with IC50 value of 2.84 μM. Compounds 8k and 8n displayed highly effective antitumor activities against MCF-7 cells, with IC50 values of 4.56 and 4.25 μM, respectively. Compounds 8a and 8n exhibited significant antiproliferative activity against A549 cells, with IC50 values of 4.11 and 4.13 μM, respectively. The pharmacological results suggest that the substituents of phenyl ring on the 1,3,4-oxadiazole are vital for modulating antiproliferative activities against various tumor cell lines.

MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

Versatile synthesis of fused tricyclic 1,2,4-triazole derivatives

(Chemical Equation Presented) The synthesis of a small series of fused tricyclic 1,2,4-triazoles is described. The key reaction is an intramolecular two-stage, one-pot reduction/cyclization sequence of a nitropyridine/oxadiazole substrate to give the key tricyclic triazole. Further standard transformations convert this template into a series of final target compounds. Copyright Pfizer Ltd.

SUBSTITUTED TRIAZOLE DERIVATIVES AS OXYTOCIN ANTAGONISTS

The present invention relates to a class of substituted triazoles of formula (I) with activity as oxytoci antagonists, uses thereof, processes for the preparation thereof and compositions containing sai inhibitors. These inhibitors have utility in a variety of therapeutic areas including sexual dysfunction particularly premature ejaculation (P.E.).