New carbocyclic nucleosides derived from indan

Article abstract of DOI:10.1081/NCN-100002503

Seven new carbocyclic nucleosides derived from indan (1a-g) were efficiently prepared from 1,2-indanedimethanol via Mitsunobu reaction with 6-chloroadenine and subsequent introduction of the appropriate substituent.

Full text of DOI:10.1081/NCN-100002503

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NEW CARBOCYCLIC NUCLEOSIDES DERIVED FROM
INDAN
a
a
a
a
b
F. Abad , F. Álvarez , F. Fernández , X. García-Mera & J. E. Rodríguez-Borges
a
Universidad de Santiago , Dpto. Química Orgánica, Facultad de Farmacia, Santiago de
Compostela, E-15706, Spain
b
Universidad de Santiago , Dpto. Química Orgánica, Facultad de Farmacia, Santiago de
Compostela, E-15706, Spain
Published online: 07 Feb 2007.
To cite this article: F. Abad , F. Álvarez , F. Fernández , X. García-Mera & J. E. Rodríguez-Borges (2001) NEW CARBOCYCLIC
NUCLEOSIDES DERIVED FROM INDAN, Nucleosides, Nucleotides and Nucleic Acids, 20:4-7, 1127-1128, DOI: 10.1081/
NCN-100002503
To link to this article: http://dx.doi.org/10.1081/NCN-100002503
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NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, 20(4–7), 1127–1128 (2001)
NEW CARBOCYCLIC NUCLEOSIDES
DERIVED FROM INDAN
´
∗
F. Abad, F. Alvarez, F. Fern a´ ndez, X. Garc ´ı a-Mera,
and J. E. Rodr ´ı guez-Borges
Dpto. Qu ´ı mica Org a´ nica, Facultad de Farmacia, Universidad
de Santiago, E-15706 Santiago de Compostela, Spain
ABSTRACT
Seven new carbocyclic nucleosides derived from indan (1a–g) were efficiently
prepared from 1,2-indanedimethanol v ´ı a Mitsunobu reaction with 6-chloroa-
denine and subsequent introduction of the appropriate substituent.
Carbovir (1) and Abacavir (2) are carbocyclic analogues of nucleosides
CANs), in both of which the core of the pseudo-sugar moiety is a cyclopentene
(
ring. Recently, others CANs with interesting antiviral properties have been pre-
pared in which a cyclopentane ring is fused to another saturated ring; this structure
appears to facilitate interaction with viral enzymes (3).
O
N
HN
N
N
N
N
HN
H N
N
H N
HO 2
N
HO 2
Carbovir
Scheme 1.
Abacavir
∗
Corresponding author.
1
127
Copyright ꢀC 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
REPRINTS
1
128
ABAD ET AL.
O
O
H
H
Mg
F
i) O3
ultrasound
ii) Me2S
95%
Br
66%
74% LiAlH4
AcO
OSO Me
AcO
OH
HO
OH
2
ClSO Me
Ac O / Pyr
2
2
NEt / DMAP
3
55%
78%
Cl
N
N
N
65%
N
H
R
N
Compound
1a
R
Yield (%)
Cl
OH
OCH3
63
65
60
54
60
N
N
N
N
1
b
N
1c
OCH CH3
N
2
N
HO
1d
NH2
2
AcO
i)RH
ii) NaOH
1
e
NHCH CH CH
2
3
1f
NHCH(CH3)2
NHCH(CH2)2
52
44
1
g
1
Scheme 2.
We hypothesize that CANs with a cyclopentene ring fused to an aromatic ring
wouldpossesstheseconformationaladvantagesandalsobemoreliposoluble, which
would favour their access to the CNS, an important reservoir for the replication of
viruses such as HIV.
We report now a suitable synthetic route to CANs of type 1, (X=OR or NHR;
R=H, alkyl or cycloalkyl). Our approach proceeds via generation of benzonorbor-
nadiene, preparationofthecorrespondingdifunctionalizeddiol, Mitsunobureaction
with 6-chloroadenine, introduction of the appropriate substituent at position 6 of
the adenine, and final deacetylation.
REFERENCES
1
2
.
.
Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
Daluge, S.M.; Good, S.S.; Faleto, M.B.; Martin, M.T.; Miller, W.H.; Averett, D.R.;
St. Clair, M.H.; Boone, L.R.; Tisdale, M.; Reardon, J.E. Antiviral Res. 1995, 26, A229.
Jeong, L.S.; Marquez, V.E. Tetrahedron Lett. 1996, 37 (14), 2353.
3.

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