882228-97-9

Usage

Abbreviation

BMC

Core Structure

Pyrazole

Functional Groups

Bromophenoxy
Aldehyde

Biological Activities

Anti-inflammatory
Analgesic

Applications

Medicinal Chemistry: Potential lead compound for drug development
Agriculture: Potential pesticide or herbicide

Interest in Scientific Community

Ongoing synthesis and study of properties and applications

Upstream product

• 99068-19-6 C₁₀H₁₂N₂O₂ 
• 6078-46-2 ethyl 3-(2-phenylhydrazono)butanoate 
• 100-63-0 phenylhydrazine 
• 89-25-8 edaravone 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 1305332-69-7 5-(4-bromophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde oxime 
• 1426300-91-5 C₂₆H₂₄BrN₃O₄S₂ 
• 1426300-79-9 C₂₆H₂₄BrN₃O₄S₂ 
• 1426300-55-1 C₂₅H₂₂BrN₃O₄S₂ 
• 1426300-39-1 C₂₂H₁₆BrN₃O₄S₂ 

Relevant academic research and scientific papers

Design, synthesis and evaluation of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties as antibacterial agents

Abstract: In the present investigation, a series of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties were synthesized and their structures were confirmed by different spectral tools. The biological evaluation in vitro revealed that some of the target compounds exerted good antibacterial and antifungal activity in comparison with the reference drugs. Among these novel hybrids, compound 10d showed the most potent activity with minimum inhibitory concentration values (MIC) of 0.5?μg/mL against S. aureus 4220, MRSA 3506 and E. coli 1924 strain. The cytotoxic activity of the compounds 6d, 6m, 10d and 10g was assessed in MCF-7 and HeLa cells. Growth kinetics study showed significant inhibition of bacterial growth when treated with different conc. of 10d. In vitro enzyme study implied that compound 10d exerted its antibacterial activity through DHFR inhibition. Moreover, significant inhibition of biofilm formation was observed in bacterial cells treated with MIC conc. of 10d as visualized by SEM micrographs. Graphic abstract: Twenty-nine target compounds were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities.[Figure not available: see fulltext.].

Green method for the synthesis of chromeno[2,3- C ]pyrazol-4(1 H)-ones through ionic liquid promoted directed annulation of 5-(aryloxy)-1 H -pyrazole-4-carbaldehydes in aqueous media

The first classical heterocyclic ionic liquid (IL) promoted C-H bond oxidant cross-coupling reaction for the intramolecular annulation of 5-(aryloxy)-1H-pyrazole-4-carbaldehydes to chromeno[2,3-c]pyrazol-4(1H)-ones has been disclosed. The promoter 1,3-dibutyl-1H-benzo[d][1,2,3]triazol-3-ium bromide can be easily recycled and reused with the same efficacies for at least five cycles in aqueous medium. The strategy works smoothly and provides an applicable protocol to construct a wide range of products.

Synthesis and evaluation on anticonvulsant activities of pyrazolyl semicarbazones

In this paper, a series of 2-[(5-phenoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-methylene]hydrazine carboxamides were synthesized and evaluated for their anticonvulsant activities using the maximal electroshock method. Their neurotoxicities were determined ap

Design and synthesis of pyrazolyl thiosemicarbazones as new anticonvulsants

A series of pyrazolyl thiosemicarbazone derivatives were synthesized and evaluated for their anticonvulsant activity using the maximal electroshock (MES) method. Interestingly, all compounds prepared showed long duration of protection effect in the MES sc

Synthesis and antibacterial evaluation of rhodanine-based 5-aryloxy pyrazoles against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA)

With an intention to synergize the anti-bacterial activity of 5-aryloxy pyrazole and rhodanine derivatives, eight series of hybrid compounds have been synthesized and evaluated for their antibacterial activity. The majority of the synthesized compounds showed good inhibitory activity against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA, QRSA) with minimum inhibitory concentration (MIC) values in the range of 1-32 μg/mL. The cytotoxicity test suggests that these compounds exhibited in vitro antibacterial activity at non-cytotoxic concentrations. These studies therefore suggest that rhodanine-based 5-aryloxy pyrazoles are interesting scaffolds for the development of novel Gram-positive antibacterial agents.

Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents

Three novel series of 5-aryloxypyrazole derivatives have been synthesized and tested for their antibacterial activity. The majority of the synthesized compounds showed potent inhibitory activity against Gram-positive bacteria Staphylococcus aureus 4220, especially against the strains of multidrug-resistant clinical isolates (MRSA3167/3506 and QRSA3505/3519). Among which compounds IIIb, IIIg and IIIm showed the most potent levels of activity (MIC = 1 μg/mL) against the multidrug-resistant strains. And cytotoxic activity assay showed that the compounds tested did not affect cell viability on the Human cervical (HeLa) cells at their MICs. The current study therefore suggests that 5-aryloxypyrazoles bearing a rhodanine-3-aromatic acid moiety are promising scaffolds for the development of novel Gram-positive antibacterial agents.

Synthesis and antitumor activity of some pyrazole derivatives

Vilsmeier-Haack chloroformylation of 1a-e using DMF and an excess of POCl3 yielded the corresponding pyrazole-4-carbaldehydes 2a-e. Reaction of 2a,c with o-bromophenol and KOH in DMF gave the target compound 5-phenoxypyrazole-4- carbaldehydes 3a,b which in turn gave the corresponding oximes 4a,b by oximation of 3a,b with hydroxylamine. Condensation of 2b,c with 1,2-diaminobenzene and 2-aminothiophenol was carried out to give tetrahydrobenzo[b]pyrazolo[3,4-e][1,4] diazepine derivatives 5a,b and benzo[b]pyrazolo[4,3- f][1,4]thiazepine derivatives 6a,b, respectively. Some of the prepared compounds was examined as cytotoxic agents. The compounds 3a, 4a, 5a and 6a were proved to be less or more active than the standared doxorubicin depending on the cell lines.