Synthesis of the Novel 3-Benzotriazole-5-yl difluoromethyl-5-trifluoromethyl benzotriazole Nucleosides

Break, Laila M.

doi:10.5539/ijc.v7n2p99

Cited by 2 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ten signals of carbon were assigned to two of the sugar moieties (see the Experimental section). The 13 C NMR of the CF3 group showed at δ121.54, 104.87 and 108.52 of Compounds 3, 6, and 7, respectively Mass: M + 493.01, 173.04 (100%) [8,9].…”

Section: Resultsmentioning

confidence: 99%

Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone

Break¹,

Al-harthi²

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

Fluorinated nucleosides are very important for increased biological and chemical stability of organ fluorine compounds. Synthesis of (1H)-8-trifluloromethyl-2-methyl-4-quinazolinone 3 from 2-amino-3-(trifluoromethyl) benzoic acid 1 was performed. Ribosylation of compound 4 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose 5 using the silylation method created the benzoylated nucleoside derivative 6. Debenzoylation of the protected nucleoside 6 via reaction with sodium metal in dry methanol to create the corresponding free nucleoside 1,3-bis-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)-8-(trifluoromethyl)-2-methyl-4-quinazolinone 7. The structures of the newly synthesis compounds have been confirmed on the basis of IR, 1HNMR, 13CNMR, and mass spectral data.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone

Break¹,

Al-harthi²

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

View full text Add to dashboard Cite

show abstract

“…[49], benzofuran-2-carbaldehyde (1q) [50], 3-(4fluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1v) [51], and 2-N-phenylbenzene-1,2-diamine (2v) [52] were synthesized according to a known procedure. Starting 4chlorobenzene-1,2-diamine (2b), 4-fluorobenzene-1,2-diamine (2c), 4,5-dimethylbenzene-1,2-diamine (2e), 4-(trifluoromethyl)benzene-1,2-diamine (2f), 4-methoxybenzene-1,2diamine (2g), 4-methylbenzene-1,2-diamine (2h), 4,5-dichlorobenzene-1,2-diamine (2i), 4nitrobenzene-1,2-diamine (2j), 3-methylbenzene-1,2-diamine (2k), 3,4-dimethylbenzene-1,2diamine (2p), 3,4-difluorobenzene-1,2-diamine (2q), 4-[ (3,4-diaminophenyl)methyl]benzene-1,2-diamine (2w), and phenazine-2,3-diamine (2x) were synthesized according to a known procedure [53]. N-Substituted phenylenediamines 2-N-methylbenzene-1,2-diamine (2r), 2-N-(propan-2-yl)benzene-1,2-diamine (2s), N-allyl-o-phenylenediamine (2t), and 2-Nbenzylbenzene-1,2-diamine (2u) were synthesized according to a known procedure [54].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Antimicrobial and Antibiofilm Activities, and Molecular Docking Investigations of 2-(1H-Indol-3-yl)-1H-benzo[d]imidazole Derivatives

Mendogralo,

Nesterova,

Nasibullina

et al. 2023

Molecules

View full text Add to dashboard Cite

The treatment of many bacterial and fungal infections remains a problem due to increasing antibiotic resistance and biofilm formation by pathogens. In the present article, a methodology for the chemoselective synthesis of 2-(1H-indol-3-yl)-1H-benzo[d]imidazole derivatives is presented. We report on the antimicrobial activity of synthesized 2-(1H-indol-3-yl)-1H-benzo[d]imidazoles with significant activity against Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 43300 (MRSA), Mycobacterium smegmatis (mc(2)155/ATCC 700084), and Candida albicans ATCC 10231. High activity against staphylococci was shown by indolylbenzo[d]imidazoles 3ao and 3aq (minimum inhibitory concentration (MIC) < 1 µg/mL) and 3aa and 3ad (MIC 3.9–7.8 µg/mL). A low MIC was demonstrated by 2-(1H-indol-3-yl)-1-methyl-1H-benzo[d]imidazole (3ag) against M. smegmatis and against C. albicans (3.9 µg/mL and 3.9 µg/mL, respectively). 2-(5-Bromo-1H-indol-3-yl)-6,7-dimethyl-1H-benzo[d]imidazole (3aq) showed a low MIC of 3.9 µg/mL against C. albicans. Compounds 3aa, 3ad, 3ao, and 3aq exhibited excellent antibiofilm activity, inhibiting biofilm formation and killing cells in mature biofilms. Molecular docking analysis identified three potential interaction models for the investigated compounds, implicating (p)ppGpp synthetases/hydrolases, FtsZ proteins, or pyruvate kinases in their antibacterial action mechanism.

show abstract

Synthesis of the Novel 3-Benzotriazole-5-yl difluoromethyl-5-trifluoromethyl benzotriazole Nucleosides

Cited by 2 publications

References 25 publications

Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone

Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone

Synthesis, Antimicrobial and Antibiofilm Activities, and Molecular Docking Investigations of 2-(1H-Indol-3-yl)-1H-benzo[d]imidazole Derivatives

Contact Info

Product

Resources

About