Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of 3,5-Bis(trifluoromethyl)phenyl-Substituted Pyrazole Derivatives as Potent Growth Inhibitors of Drug-Resistant Bacteria.

ABSTRACT: Enterococci and methicillin-resistant S. aureus (MRSA) are among the menacing bacterial pathogens. Novel antibiotics are urgently needed to tackle these antibiotic-resistant bacterial infections. This article reports the design, synthesis, and antimicrobial studies of 30 novel pyrazole derivatives. Most of the synthesized compounds are potent growth inhibitors of planktonic Gram-positive bacteria with minimum inhibitory concertation (MIC) values as low as 0.25 µg/mL. Further studies led to the discovery of several lead compounds, which are bactericidal and potent against MRSA persisters. Compounds 11, 28, and 29 are potent against S. aureus biofilms with minimum biofilm eradication concentration (MBEC) values as low as 1 µg/mL.

SUBMITTER: Alkhaibari IS

PROVIDER: S-EPMC8398255 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Design, synthesis, and antibacterial activity of <i>N</i>-(trifluoromethyl)phenyl substituted pyrazole derivatives.

Project description:Design and synthesis of N-(trifluoromethyl)phenyl substituted pyrazole derivatives and their potency as antimicrobial agents are described. Several of these novel compounds are effective growth inhibitors of antibiotic-resistant Gram-positive bacteria and prevent the development of biofilms by methicillin-resistant Staphylococcus aureus (MRSA) and Enterococcus faecalis. These compounds eradicated the preformed biofilms effectively and were found to be more effective than the control antibiotic vancomycin. Potent compounds showed low toxicity to cultured human embryonic kidney cells with a selectivity factor of >20. The most promising compound is very potent against meropenem, oxacillin, and vancomycin-resistant clinical isolates of Enterococcus faecium. Investigations into the mode of action by performing macromolecular synthesis inhibition studies showed a broad range of inhibitory effects, suggesting targets that have a global effect on bacterial cell function.

| S-EPMC8528206 | biostudies-literature

3,5-Bis(4-fluoro-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

Project description:In the title compound, C(21)H(16)F(2)N(2), the dihedral angle between the fluoro-phenyl groups is 66.34?(8)°, and the dihedral angle between the envelope-configured pyrazole group (N/N/C/C/C) and the benzene ring is 11.50?(9)°. The dihedral angles between the benzene and the two fluoro-substituted phenyl groups are 77.7?(6) and 16.7?(5)°. Weak C-H?? interactions contribute to the stability of the crystal structure.

| S-EPMC3007318 | biostudies-literature

3,5-Bis(4-methyl-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

Project description:In the title compound, C(23)H(22)N(2), the dihedral angle between the methyl-benzene groups is 77.62 (6)°, and the dihedral angle between the envelope-shaped pyrazole ring [in which one C atom displaced by 0.109 (1) Å from the mean plane of the other four atoms] and the phenyl ring is 17.57 (7)°. The dihedral angles between the phenyl ring and the two methyl-benzene rings are 13.24 (6) and 81.02 (7)°. In the crystal, weak C-H⋯π inter-actions link the mol-ecules.

| S-EPMC3099927 | biostudies-literature

3,5-Bis(4-meth-oxy-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

Project description:In the title compound, C(23)H(22)N(2)O(2), the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth-oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C-H⋯π stacking inter-actions and weak π-π inter-actions [centriod-centroid distance = 3.891 (2) Å].

| S-EPMC3051598 | biostudies-literature

Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives.

Project description:A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC50 values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.

| S-EPMC6968685 | biostudies-literature

3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde.

Project description:In the title mol-ecule, C(12)H(12)N(2)O, the five- and six-membered rings form a dihedral angle of 68.41?(16)°. The aldehyde group is nearly coplanar with the pyrazole ring [C-C-C-O torsion angle = -0.4?(5)°]. The three-dimensional architecture is sustained by weak C-H?O and C-H?? inter-actions.

| S-EPMC3344012 | biostudies-literature

catena-Poly[[diiodidocadmium]-?-[4,4'-(2,3,5,6-tetra-methyl-1,4-phenyl-ene)bis-(methyl-ene)]bis-(3,5-dimethyl-1H-pyrazole)-?N:N].

Project description:The heterocylic ligand of the polymeric title compound, [CdI(2)(C(22)H(30)N(4))], links two adjacent CdI(2) units, forming a chain running parallel to [[Formula: see text]01]. The Cd(II) atom is located on a twofold rotation axis and shows a distorted tetra-hedral CdI(2)N(2) coordination. The mid-point of the benzene ring of the ligand lies on a center of inversion. There are no classical hydrogen-bonding inter-actions present.

| S-EPMC3212128 | biostudies-literature

3,5-Bis(4-bromo-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

Project description:In the title compound, C(21)H(16)Br(2)N(2), the central pyrazole ring adopts an flattened envelope conformation, with the stereogenic C atom in the flap position. The deviations from planarity for this ring are relatively minor (r.m.s. deviation = 0.045?Å) and the dihedral angles formed with the N- and C(imine)-bound benzene rings are 7.73?(13) and 11.00?(13)°, respectively. By contrast, the benzene ring bound at the chiral C atom is almost orthogonal to the rest of the mol-ecule; the dihedral angle formed between this ring and the pyrazole ring is 79.53?(13)°. In the crystal, the packing is stabilized by C-H?N and C-H?Br inter-actions.

| S-EPMC2979444 | biostudies-other

Synthesis and Antimicrobial Studies of Coumarin-Substituted Pyrazole Derivatives as Potent Anti-Staphylococcus aureus Agents.

Project description:In this paper, synthesis and antimicrobial studies of 31 novel coumarin-substituted pyrazole derivatives are reported. Some of these compounds have shown potent activity against methicillin-resistant Staphylococcus aureus (MRSA) with minimum inhibitory concentration (MIC) as low as 3.125 µg/mL. These molecules are equally potent at inhibiting the development of MRSA biofilm and the destruction of preformed biofilm. These results are very significant as MRSA strains have emerged as one of the most menacing pathogens of humans and this bacterium is bypassing HIV in terms of fatality rate.

| S-EPMC7356691 | biostudies-literature

Bis[?-3,5-bis-(pyridin-2-yl)-1H-pyrazole]-bis-[di-bromido-iron(III)].

Project description:The title dinuclear complex, [Fe2Br4(C13H9N4)2], which lies on an inversion center, features two approximately planar bis-(pyridin-2-yl)pyrazole (bpypz(-)) ligands [maximum deviation = 0.082?(3)?Å] and four bromide ions. Each Fe(III) ion is octa-hedrally coordinated by four N atoms of two bpypz(-) ligands and two Br ions. ?-? stacking inter-actions [centroid-centroid distances = 3.7004?(17)-4.0123?(18)?Å] are observed between pyridyl and pyrazole rings, and between pyridyl and pyridyl rings of adjacent complex mol-ecules.

| S-EPMC3884243 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data