111858-63-0Relevant academic research and scientific papers
CATALYTIC ACYLATION OF BENZOXAZOLIN-3-ONES IN THE PRESENSCE OF ZINC CHLORIDE
Mukhamedov, N. S.,Kristalovich, E. L.,Plugar, V. N.,Giyasov, K.,Aliev, N. A.,Abdullaev, N. D.
, p. 982 - 984 (1994)
In the acylation of benzoxazolin-2-ones by aromatic acid chlorides in the presence of 10-2 mole ZnCl2, the yields of the corresponding 6-aroylbenzoxazolin-2-ones depend on the electronegativity of the acylating agent and the nucleophilicity of
'Fries like' rearrangement: A novel and efficient method for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones
Ucar, Huseyin,Van Derpoorten, Kim,Depovere, Paul,Lesieur, Daniel,Isa, Majed,Masereel, Bernard,Delarge, Jacques,Poupaert, Jacques H.
, p. 1763 - 1772 (2007/10/03)
6-Acyl-2(3H)-benzoxazolone and 6-acyl-2(3H)-benzothiazolone derivatives have particularly interesting anti-inflammatory, antiepileptic, analgesic and antiviral properties. In this study, we report an original method of acylation on the 6-position of 2(3H)-banzoxazolone and 2(3H)benzothiazolone which consists in a two-step procedure involving migration of the acyl group from the N-position to the 6-position of the hetexocycle, at 165 °C and catalyzed by AlCl3. This new procedure was found to be more efficient with regard to the consumption of AICI3 and the yield (76-90%) than other acylation methods previously described.
Synthesis and antibacterial and antifungal properties of thiazolinoethyl-2(3H)-benzoxazolone derivatives. II
Erol,Aytemir,Yulug
, p. 731 - 734 (2007/10/03)
Cyano derivatives of 6-acyl-2(3H)-benzoxazolones were reacted with cysteamine HCl in ethanol to give the corresponding 6-acyl-3-thiazolinoethyl-2(3H)-benzoxazolones and their antibacterial and antifungal activities were investigated. The chemical structures were proved by means of their IR and 1H-NMR spectra and elemental analysis. Investigation of antimicrobiaI activity of the compounds was carried out by tube dilution and disc techniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853 and Streptococcus faecalis ATCC 29212) and yeast-like fungi (Candida parapsilosis, C albicans, C pseudotropicalis and C stellatoidea). Inhibitory effects were observed for many compounds against S aureus and Bacillus subtilis. Compounds 13 and 15 had minimum inhibitory concentrations (MIC) of 8.4 and 4.2 μg/mL respectively. The antifungal studies against C albicans (10 and 16, MIC = 67.5 μg/mL), C parapsilosis (15, MIC = 67.5 μg/mL) and C stellaatoidea (9, MIC = 67.5 μg/mL) were more successful in comparison.
Analgesic and antiinflammatory activity screening of 6-acyl-3-piperidinomethyl-2(3H)-benzoxazolone derivatives
Erol,Demirdamar
, p. 663 - 666 (2007/10/02)
6-Acyl-2(3H)-benzoxazolone derivatives were reacted with appropriate piperidine derivatives and formaldehyde in methanol to give the corresponding 6-acyl-3-piperidinomethyl-2(3H)-benzoxazolones. The obtained compounds were screened for their analgesic and antiinflammatory activities. Analgesic activity of these compounds was investigated by modified Koster test. Antiinflammatory activity was assayed by using carrageenan induced mouse paw edema test and arachidonic acid edema. The 15 compounds synthesized showed good analgesic activities; compounds 1, 3 and 6 moved to be active inhibitors of edema.
Synthesis of some new Mannich bases derived from 6-acyl-3-(3,5-dimethylpiperidinomethyl)-2(3H)-benzoxazolones and their biological activities
Erol,Rosen,Erdogan,Yulug
, p. 851 - 853 (2007/10/02)
A number of 6-acyl-3-(3,5-dimethylpiperidinomethyl)-2(3H)-benzoxazolones have been synthesized by Mannich reaction and their antibacterial and antifungal activities have been tested. Their chemical structures have been proved by means of their IR, NMR, mass spectroscopic data and by elementary analysis. Investigation of antimicrobial activity of compounds was done by tube dilution and paper disc techniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Staphylococcus faecalis RSKK 10541) and yeast-like fungi (Candida parapsilosis, Candida albicans, Candida pseudotropicalis, Candida stellatoidea). Among the compounds tested 6-(2-chlorobenzoyl)-3-(3,5-dimethylpiperidinomethyl)-2(3H)-benzoxazolone (Compound 2) and 6-(3-chlorobenzoyl)-3-(3,5-dimethylpiperidinomethyl)-2(3H)-benzoxazolone (Compound 3) showed the most favorable activity.
