38874-88-3Relevant academic research and scientific papers
Synthetic and theoretical investigation on nano-Au/TiO2 catalyzed hydrothiolation for construction of C─S bond: Experimental and DFT study
Turukarabettu, Vishwanath,Kalluraya, Balakrishna
, (2020)
In this article, we describe a new synthetic and theoretical approach for the construction of C─S bond in heterocyclic molecules undergoing nanogold catalytic hydrothiolation reaction. The experimental studies showed that the reaction proceeded via regioselective Michael-type anti-addition and gave the corresponding sulfur bridged 1,3,4-oxadiazole-propenone in excellent yield. The compounds were characterized by analytical and spectral techniques. A gas phase molecular modeling study of nanogold-catalyzed hydrothiolation of acetylenic ketone with 5-aryl-1,3,4-oxadiazol-2-thiol was carried out using density functional theory (DFT) calculations. It showed the adsorption of acetylenic ketone on nanogold and preferable coordination at the β carbon of the alkyne group. The charge calculations showed that on adsorption over nanogold, the alkyne group became more polar in nature. The frontier highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) analysis showed a possible overlap of molecular orbitals between thiol and acetylenic β carbon to give Z isomer. The experimental and theoretical validation of bond parameters was carried out. A possible mechanism of hydrothiolation reaction was proposed based on the analogy with the results of theoretical calculations and experimental evidence.
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.].
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.
Reactions of aryloxyacetylhydrazines with α,β-acetylinic ketones
Holla, B Shivarama,K, Shridhara
, p. 1139 - 1141 (2007/10/02)
Reactions of aryloxyacetyl hydrazines with 1-aryl-3-(5-nitro-2-furyl)-2-propyn-1-ones (3) yield 5-aryl-1-aryloxyacetyl-5-hydroxy-3-(5-nitro-2-furyl)-pyrazolines (4) rather than the expected pyrazoles (5).These hydroxypyrazolines have been subjected to acid-catalyzed dehydration.Dehydration using con. sulfuric acid in refluxing ethanol yields 5-aryl-3-(5-nitro-2-furyl)pyrazoles (6) while on stirring with a few drops of con. sulphuric acid in gl. acetic acid results in the formation of 5-aryl-1-aryloxyacetyl-3-(5-nitro-2-furyl)pyrazoles (5).
