32023-50-0Relevant academic research and scientific papers
Design and synthesis of sulfur cross-linked 1,3,4-oxadiazole-nitro(furan/thiophene)-propenones as dual inhibitors of inflammation and tuberculosis: molecular docking and Hirshfeld surface analysis
Turukarabettu, Vishwanath,Kalluraya, Balakrishna,Sharma, Monika
, p. 1999 - 2010 (2019/11/16)
Abstract: A series of 3-[5-nitro(furan/thiophene)-2-yl]-1-aryl-3-(5-aryl-1,3,4-oxadiazol-2-ylthio)prop-2-en-1-one derivatives was synthesized and studied with the aim of developing dual inhibitors of multidrug-resistant tuberculosis and inflammation. The in vivo anti-inflammatory activity results showed excellent inhibition of rat paw edema. The methoxybenzene/nitrofuryl derivative of title compounds showed 83% inhibition of inflammation during 2–6?h after carrageenan injection. All compounds showed anti-tuberculosis activity at MIC of 50?μg/cm3. The molecular docking studies revealed that the oxadiazole and nitrofuran groups played a significant role in the inhibiting site of the enzymes COX1, COX2, 5-LOs, and InhA by forming hydrogen bonding with Tyr 385, Ser 530, Tyr 467, and Tyr 158 amino acid residues, respectively. The novel compounds are active antibacterial agents with potential inhibition on E. coli bacteria. The toxicity results showed good percentage viability of human kidney cell lines with IC50 value greater than 100?μg/cm3 concentration. The Hirshfeld surface analysis and electrostatic potential map of compound showed good intermolecular contacts and hydrogen bonding donor and acceptor potential. Graphic abstract: [Figure not available: see fulltext.].
Regioselective synthesis of nitrofuran containing novel spiropyrrolidine library through 1,3-dipolar cycloaddition reactions
Mallya, Sahana,Kalluraya, Balakrishna,Girisha
, p. 527 - 531 (2015/03/30)
A novel series of nitrofuran containing spiropyrrolidines has been synthesized with high regioselectivity in moderate to excellent yields via 1,3-dipolar cycloaddition reaction of azomethine ylides with various substituted chalcones.
Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop- 2-en-1-one derivatives as potent antitubercular agents
Tawari, Nilesh R.,Bairwa, Ranjeet,Ray,Rajan,Degani, Mariam S.
experimental part, p. 6175 - 6178 (2010/11/19)
Based on stereoelectronic feature analysis using density functional theory (DFT) at B3LYP/3-21G level, a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives with low LUMO energies (90/CC50: >1800). Thus, this study shows the potential of stereoelectronic property analysis in developing improved nitroaromatics as antitubercular agents.
Synthesis and antibacterial properties of nitrofuryltriazolothiadiazepines
Holla, B. Shivarama,Shridharab,Shivananda
, p. 3113 - 3116 (2007/10/03)
Methyl aryl ketones 1 on reaction with 5-nitrofurfuraldehyde 2 give 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones 3 which on bromination affords 2,3-dibromo-1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones 4. Debromination of 4 by triethylamine in benzene results in 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones 5 which on condensation with 3-substituted-4-amino-5-mercapto-1,2,4-triazole 6 furnishes Michael adducts 7. The Michael adduct 7 undergoes cyclization in conc. sulphuric acid to give 3-aryloxymethyl-6-aryl-8-(5-nitro-2-furyl)-1,2,4-triazolothiadiazepines 8. Antibacterial activity of 7 and 8 has been reported.
