75843-20-8Relevant academic research and scientific papers
Synthesis and antimicrobial activity evaluation of novel 4-thiazolidinones containing a pyrone moiety
Nechak, Rosa,Bouzroura, Samia Aichouche,Benmalek, Yamina,Salhi, Lydia,Martini, Sophie P.,Morizur, Vincent,Dunach, Elisabet,Kolli, Bellara Nedjar
, p. 262 - 272 (2015)
A series of thiosemicarbazones 3a-d and 4-thiazolidinones 5a-d, 7a-d, and 9a-h were synthesized and evaluated for their in vitro antimicrobial activity. Condensation of 3-acetyl-4-hydroxy-6-methyl-2H pyran-2-one1 (dehydroacetic acid) with thiosemicarbazide 2a-d in ethanol at room temperature yielded the thiosemicarbazones 3a-d. These compounds were exploited to synthesize the 4-thiazolidinones 5a-d via their reactions with ethyl 2-bromo propionate4. Derivatives 7a-d were prepared by reaction of the thiosemicarbazones 3a-d with phenyl bromoacetate 6. The 4-thiazolidinones 9a-h were obtained by treatment of compound 3a or 3c with maleimide derivatives 8a-d in refluxing ethanol, under sulfuric acid catalysis. All compounds were screened in vitro for their antibacterial and antifungal activities against five human pathogens microorganisms: Escherichia coli ATCC 25992, Pseudomonas aeruginosa ATCC 27852, Staphylococcus aureus ATCC 43300, Staphylococcus aureus ATCC 25923, and Candida albicans.
Ruthenium(II) carbonyl complexes of dehydroacetic acid thiosemicarbazone: Synthesis, structure, light emission and biological activity
Kannan, Sethuraman,Sivagamasundari,Ramesh,Liu, Yu
, p. 2251 - 2257 (2008)
The reaction of [RuHCl(CO)(B)(EPh3)2] (where E = As, B = AsPh3; E = P, B = PPh3, py, pip, or mor) and dehydroacetic acid thiosemicarbazone (abbreviated as H2dhatsc where H2 stands for the two dissociable protons) in benzene under reflux afford a series of new ruthenium(II) carbonyl complexes containing dehydroacetic acid thiosemicarbazone of general formula [Ru(dhatsc)(CO)(B)(EPh3)] (where E = As, B = AsPh3; E = P, B = PPh3, py, pip or mor; dhatsc = dibasic tridentate dehydroacetic acid thiosemicarbazone). All the complexes have been characterized by elemental analyses, FT-IR, UV-Vis, and 1H NMR spectral methods. The thiosemicarbazone of dehydroacetic acid behaves as dianionic tridentate O, N, S donor and coordinates to ruthenium via phenolic oxygen of dehydroacetic acid, the imine nitrogen of thiosemicarbazone and thiol sulfur. In chloroform solution, all the complexes exhibit metal-to-ligand charge transfer transitions (MLCT). The crystal structure of one of the complexes [Ru(dhatsc)(CO)(PPh3)2] (1) has been determined by single crystal X-ray diffraction which reveals the presence of a distorted octahedral geometry in the complexes. All the complexes exhibit an irreversible oxidation (RuIII/RuII) in the range 0.76-0.89 V and an irreversible reduction (RuII/RuI) in the range -0.87 to -0.97 V. Further, the free ligand and its ruthenium complexes have been screened for their antibacterial and antifungal activities. The complexes show better activity in inhibiting the growth of bacteria Staphylococcus aureus and Escherichia coli and fungus Candida albicans and Aspergillus niger. These results made it desirable to delineate a comparison between free ligand and its ruthenium complexes.
Synthesis and antimicrobial evaluation of some 1-(4-arylthiazol--2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[4,5′-bi-1H-pyrazol]-5-ols
Mor, Satbir,Mohil, Rajni,Nagoria, Savita,Kumar, Ashwani
, p. 127 - 139 (2017/03/27)
A series of sixteen 1-(4-arylthiazol-2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[ 4,5′-bi-1H-pyrazol]-5-ols (7a.p) was synthesized starting from dehydroacetic acid (DHA, 1) via the stepwise formation of thiosemicarbazone (2), 3-(1-(2-(4-arylthiazol-2-yl)hydrazono)ethyl)-4-hydroxy-6-methyl-2H-pyran- -2-ones (4a.d) and 1-(1-(4-arylthiazol-2-yl)-5-hydroxy-3-methyl-1H-pyrazol- -4-yl)butane-1,3-diones (5a.d) in high yields. The in vitro antibacterial and antifungal activities of the synthesized bipyrazoles 7a.p were investigated against two Gram-positive bacterial strains, viz. Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443), one Gram-negative bacterial strain, viz. Escherichia coli (MTCC 42), and two fungal strains, viz. Candida albicans (MTCC 183) and Aspergillus Niger (MTCC 282). The compounds 7a and 7e were found to exhibit better inhibitory activity against A. Niger than the reference fluconazole. Moreover, the antifungal activities of the title compounds were more prolific than their antibacterial activities. Furthermore, in order to study binding interactions, docking simulations of compounds 7a, 7m and 7o were performed into the active site of S. aureus 1,4-dihydroxy-2-naphthoyl- -CoA synthase.
Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles
Mor, Satbir,Mohil, Rajni,Kumar, Devinder,Ahuja, Munish
, p. 3541 - 3548 (2013/02/23)
A series of isoxazolyl thiazolyl pyrazoles 5a-d was synthesized by multi-step process, starting from 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (dehydroacetic acid, DHAA) 1. DHAA 1 was easily converted to thiosemicarbazone 2 which on reaction with a-βromo
