Synthesis of heterocylic compounds of biological interest from carbohydrate derivatives

Article abstract of DOI:10.3390/50300418

The synthesis of some isoxazolic compounds from carbohydrate derivatives is described. These products are obtained by 1,3-dipolar cycloaddition reaction and their functionalization leads to derivatives with potential biological activities.

Full text of DOI:10.3390/50300418

418
Molecules 2000, 5
Synthesis of Heterocylic Compounds of Biological Interest from
Carbohydrate Derivatives
M. F. Martinez Esperón, M. L. Fascio and N. B. D’Accorso
Centro de Investigaciones de Hidratos de Carbono (CIHIDECAR). Departamento de Química Or-
gánica. Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Ciudad Universitaria,
Pab. II 1428, Buenos Aires, Argentina
E-mail: norma@qo.fcen.uba.ar
Abstract: The synthesis of some isoxazolic compounds from carbohydrate derivatives is
described. These products are obtained by 1,3-dipolar cycloaddition reaction and their func-
tionalization leads to derivatives with potential biological activities.
Introduction
The isoxazoles derivatives are a family of interesting compounds due to their biological activities.
Some of these are used as muscle relaxants [1] and for the treatment of hypercholesteremia, arterio-
sclerosis, and hyperlipidemia [2].
In previous papers we performed the synthesis of 3-glycosyl-5-substituted-2-isoxazoles by 1,3-
dipolar cycloaddition, where the N-oxide came from protected carbohydrate derivatives [3]. In this
work we describe the deprotection and functionalization of the polihydrated moiety as synthetic pre-
cursors of new di-heterocyclic compound.
Experimental part
Ph
Ph
O
O
N
CH2OH
N
O
a)
O
OH
OH
b)
O
OH, H
OH
H,OH
OH
O
O
OH
H
H
OH
Ph
1
2
Ph
O
N
Ph
O
O
N
N
c)
BzO
H
BzO
H
OBz
H
d)
BzO
H
BzO
H
OBz
H
N
O
OH
NHOH,H
X = NH; Y = N
X = O; Y = C
H
OH
N
Y
C
X
N
R
3
4

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Molecules 2000, 5
The following synthetic route is applied.
Results and discussion
The 3-(1’,2’-O-isopropylidene-α-D-xilofuranos-4’-il)-5-phenyl-2-isoxazol (1) was obtained by 1,3-
dipolar cycloaddition, where the N-oxide was a glucose derivative and the dipolarophile was phen-
ylacetylene. The treatment of compound 1 with acetic acid (10%) yielded compound 2. The reaction of
2 with hydroxylamine gave the oxime (3). The benzoylation of the oxime allowed us to obtain the ni-
trile 4, which is the suitable synthetic intermediate to prepare different heterocyclic compound with
biological interest.
All the compounds were characterized for 1H-MNR, 13C y mass spectrometry.
Acknowlegments: The authors thank to UBA and CONICET for financial support research and to
UMYMFOR for mass spectra.
References and Notes
1. Mitsui Toatsu Chemicals; Mitsui Seiyaku Kogyoo, K.K; Toyama Chemical Co. Ltd. Jpn. Kokai
1994, 06, 116-146.
2. Marquis, E. T.; Sanderson, J. R. US Pat. 52833356 (1994) (Chem. Abstr., 1994, 120, 217 649).
3. Fascio, M. L.; Montesano, V. J.; D’Accorso, N. B. J. Carbohydrate Chem., accepted.