538
M. Ko¨ksal et al. / Il Farmaco 57 (2002) 535–538
3. Results and discussion
References
All the compounds were synthesized using the pro-
cedure given in the above by reacting 2-benzoxazoli-
none sodium salt with appropriate phenacyl bromide
in ethanol. The synthesis results are presented in
Table 1. The IR and 1H NMR spectra of the com-
pounds are given to evidence the structure of the
compounds. Spectral data of 6-acyl-3-(4-substituted
[1] A. Lespagnol, M. Durbet, G. Mongy, Sur le pouvoir hypnotique
de la benzoxazolone, Comp. Rend. Soc. Biol. Lille 135 (1941)
1255–1258.
[2] J. Sam, J.L. Valentine, Preparation and properties of 2-benzoxa-
zolinones, J. Pharm. Sci. 58 (1969) 1043–1054.
[3] R.L. Clark, A.A. Pessolano, Synthesis of some substituted benzox-
azolinones, J. Am. Chem. Soc. 80 (1953) 1662–1664.
[4] R.S. Varma, W.L. Nobles, Synthesis and antibacterial activity of
certain 3-substituted benzoxazolinones, J. Pharm. Sci. 57 (1968)
39–44.
[5] N. Go¨khan, H. Erdog˘an, B.C. Tel, R. Demirdamar, Analgesic and
antiinflammatory activity screening of 6-Acyl-3-piperidinomethyl-
2-benzoxazolinone derivatives, Eur. J. Med. Chem. 31 (1996)
625–628.
benzoylmethyl)-2-benzoxazolinone
derivatives
are
shown in Table 2. Antimicrobial activity results of the
compounds were evaluated against two Gram-posi-
tive, one Gram-negative bacteria, and three different
fungi by comparing with standards. These results are
given in Table 3.
[6] M.P. Vaccher, D. Lesieur, C. Lespagnol, J.P. Bonte, J. Lamar, M.
Beaughard, G. Dureng, Benzoxazolinone phenylethanolamines:
adrenergic receptor antagonists, chemical and pharmacodynamic
study, Farmaco Ed. Sci. 41 (1986) 257–269.
4. Conclusions
[7] R.S. Varma, A. Kapoor, Potential biologically active agents. Part
XXI. 1-(4-Benzoxazolylmethylaminobenzoyl)morpholines and
piperidines as antimicrobial agents, Indian J. Chem. 18B (1979)
200–204.
[8] D.D. Erol, H. Erdog˘an, N. Yulug˘, Synthesis and biological
activity of 6-acyl-3-substituted-2(3H)-benzoxazolinones, J.
Pharm. Belg. 44 (1989) 334–336.
[9] V. Kalcheva, Z. Mincheva, P. Andreeva, Synthesis and in vitro
activity of new cephalosporin derivatives containing a benzoxa-
zolone ring, Arzneim. Forsch. 40 (1990) 1030–1034.
[10] E.M. Basel, J.B. Riehen, US Patent 2,922,794 (Cl. 260–304),
January 26, 1960.
The structure of the compounds was confirmed by
IR, 1H NMR and elemental analysis. In IR spectra
of the compounds, the bands seen at 1775–1785 (lac-
tam CꢁO) and 1680–1705 (CH2ꢀCꢁO)/cm are in ac-
cordance with the assumed structures. Furthermore,
NꢀH stretching bands belonging to 2-benzoxazolinone
ring disappeared with the reaction of benzoylmethyl
1
bromides. In the H NMR spectra of the compounds,
the signals of aromatic ring protons were observed as
multiplet at about 7.00–8.00 ppm and methylene pro-
tons were seen as singlets at 5.2–5.7 ppm that proved
the presence of benzoylmethyl moiety. In elemental
analysis the results support the structures with
90.4% of the theoretical values. Antimicrobial activ-
ity results of the compounds were evaluated against
two Gram-positive, one Gram-negative bacteria, and
three different fungi by comparing with standards.
[11] J.P. Bonte, D. Lesieur, C. Lespagnol, M. Cazin, C. Brunet, J.C.
Cazin, Acyl-6-benzoxazolinones, Eur. J. Med. Chem. Chim. Ther.
9 (1974) 491–497.
[12] H. Erdog˘an, M. Debaert, J.C. Cazin, Synthesis of some 2-benzox-
azolinone derivatives and their analgesic properties, Arzneim.-
Forsch./Drug Res. 41 (1991) 73–76.
[13] T. Immediate, A.R. Day, Naphthyl derivatives of ethanolamine
and N-substituted ethanolamines, J. Org. Chem. 5 (1940) 512–
518.
[14] D.D. Erol, M.D. Aytemir, Synthesis of ethanone and ethanol
derivatives of 2-benzoxazolinone: potent analgesic and antiinflam-
matory compounds inhibiting prostaglandin E2, II Farmaco 50
(1995) 167–173.
[15] National Committee for Clinical Laboratory Standards, Methods
for dilution antimicrobial susceptibility tests for bacteria that grow
aerobically, Approved Standard, M7-A4, Viallanova, PA, 1997.
[16] National Committee for Clinical Laboratory Standards, Refer-
ence method for broth dilution antifungal susceptibility testing of
yeasts, Approved Standard, M27-A, Viallanova, PA, 1997.
Acknowledgements
We would like to thank the Research Fund of
Hacettepe University (project number: 00.02.301.002)
for financial support of this research.