111846-31-2Relevant academic research and scientific papers
'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.
3-Substituted piperazinomethyl benzoxazolinones. Analgesic and anti-inflammatory compounds inhibiting prostaglandin E2
Palaska,Unlu,Ozkanli,Pilli,Erdogan,Safak,Demirdamar,Gumusel,Duru
, p. 693 - 696 (2007/10/02)
Fourty-three new benzoxazolinone derivatives having a piperazinomethyl group at the third position of the ring were synthesized by using appropriate benzoxazolinones and 4-substituted piperazines via a Mannich reaction. The structures of the compounds were elucidated by spectral data and microanalyses. Analgesic activities were evaluated by a modified Koster test. All compounds, except 7, 14, 21, 32 and 41, showed analgesic activity higher than that of acetylsalicylic acid. The compounds were also screened for their anti-inflammatory activity using a carrageenan paw edema test, and those exhibiting high anti-inflammatory activity were investigated for their ability to inhibit prostaglandin E2 induced paw edema. The results of anti-inflammatory testing indicated that most of the compounds were more active than indomethacin. Ulcerogenic activities of the compounds were also studied and no gastrointestinal bleeding was observed at the 100 mg/kg dose level.
Some new benzoxazolinone derivatives with analgesic and anti-inflammatory activities
Pilli,Erdogan,Sunal
, p. 1351 - 1354 (2007/10/02)
Fourteen new 6-acyl-2-benzoxazolinone, ethyl-(6-acyl-2-benzoxazolinone)acetate and (6-acyl-2-benzoxazolinone-3-yl) acetic acid derivatives were synthesized, and their physical properties and UV absorption data were determined. Their chemical structures we
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.
