Seco C-nucleoside analogs of the 1,2,4-triazole

Article abstract of DOI:10.1081/NCN-100002455

The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D-galacto-pentitol-1-yl)-1H-1,2,4-triazoles (6 and 7) were obtained in one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (

Full text of DOI:10.1081/NCN-100002455

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SECO C-NUCLEOSIDE ANALOGS OF THE 1,2,4-
TRIAZOLE
El Sayed H. El Ashry a & Laila F. Awad a
a Chemistry Department, Faculty of Science , Alexandria University , Alexandria, Egypt
Published online: 07 Feb 2007.
To cite this article: El Sayed H. El Ashry & Laila F. Awad (2001) SECO C-NUCLEOSIDE ANALOGS OF THE 1,2,4-TRIAZOLE,
Nucleosides, Nucleotides and Nucleic Acids, 20:4-7, 901-902
To link to this article: http://dx.doi.org/10.1081/NCN-100002455
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NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, 20(4–7), 901–902 (2001)
SECO C-NUCLEOSIDE ANALOGS
OF THE 1,2,4-TRIAZOLE
El Sayed H. El Ashry∗ and Laila F. Awad
Chemistry Department, Faculty of Science,
Alexandria University, Alexandria, Egypt
ABSTRACT
The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D-galacto-
pentitol-1-yl)-1H-1,2,4-triazoles (6 and 7) were obtained in one pot by
deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-
1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite
in orthophosphoric acid and subsequent acetylation. The structures were con-
firmed by using 1H, 13C and 2D NMR spectra, DQFCOSY, HMQC and HMBC
experiments. The favored conformational structures were deduced from the
vicinal coupling constants of the protons.
The biological activity of naturally occuring C-nucleosides has stimulated
extensive research for the synthesis of their analogues (1–3). Some acyclic
C-nucleosides of the 1,2,4-triazole have potential biological activities as antivi-
ral, herbicides, fungicides or insecticides. A part of our ongoing research program
has been devoted to the synthesis of acyclo N- and C-nucleosides (4,5). Thus, a
novel synthesis of acyclo C-nucleosides of the 1,2,4-triazole is the subject of this
work. The synthesis has been achieved by reaction of 3-(D-alditol-1-yl)-4-amino-
5-mercapto-1,2,4-triazole (4) (1,2) at O◦C with sodium nitrite in orthophosphoric
acid followed by neutralization with sodium hydroxide. The products of the tria-
zole type 4 and 5 have been obtained which could be isolated upon acetylation with
acetic anhydride in pyridine whereby the respective crystalline products 6 and 7
were obtained in 52 and 48% yield, respectively.
∗Corresponding author.
901
ꢀ
C
Copyright 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
REPRINTS
902
EL ASHRY AND AWAD
In order to establish that the formation of 3-substituted-1H-1,2,4-triazole from
4-amino-5-mercapto-3-substituted-1,2,4-triazole has taken place via the diazotiza-
tion step and not under the condition of acetylation, the model compound 4-amino-
5-mercapto-3-methyl-1,2,4-triazole (3) was diazotized under the same reaction
conditions whereby it gave 8 which was identical with an authentic sample.
H
N
H
N
N
HS
H
H
i NaNO / H PO
4
2
3
Ac O / Py
2
N
N
N
ii
NaOH / H O
N
2
H N
2
N
N
R
(CHOH)
(CHOAc)
4
4
CH OAc
1 R = D-gluco
2 R = D-galacto
3 R = Me
CH O H
4 D-gluco
5 D-galacto
2
2
6 D−gluco-Ac
D−galacto-Ac
7
NaNO / H PO
4
i
2
3
ii
NaOH / H O
2
H
N
H
N
N
Me
8
REFERENCES
1. Watanabe, K. A. The Chemistry of C-Nucleosides in Townsend, L. B., Ed.; Chemistry
of Nucleosides and Nucleotides, Vol. 3, Plenum Press, New York, 1994, pp. 421–435;
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2. Knutsem, L. J. S. Nucleosides Nucleotides, 1992, 11, 961–983; Hacksell, U.; Daves Jr.,
G. D. Progr. Med. Chem., 1985, 22, 2–65; Chu, C. K.; El-Kabbani, F. M.; Thompson,
B. B. Nucleosides Nucleotides, 1984, 3, 1–31.
3. Buchanan, J. G. Fortschr. Chem. Org. Nat. Prod, 1983, 44, 243–299; Ogura, H.;
Takahashi, H. Yuki Gosei Kagaku Kyokaishi, 1980, 38, 756–768; Chem. Abstr., 1981,
94, 157143n.; James, S. R. J. Carbohydr. Nucleosides Nucleotides, 1979, 6, 417–465.
4. Awad, L. F.; El Ashry, E. S. H. Carbohydr. Res., 1998, 312, 9–22; El Ashry, E. S. H.;
Awad, L. F.; Winkler, M. J. Chem. Soc., Perkin. Trans. 1, 2000, 829–834.
5. El Ashry, E. S. H.; El Kilany, Y. Adv. Heterocycl. Chem., 1997, 67, 391–432; El Ashry,
E. S. H.; El Kilany, Y. Adv. Heterocycl. Chem., 1997, 68, 1–88; El Ashry, E. S. H.;
El Kilany, Y. Adv. Heterocycl. Chem., 1998, 69, 129–215.

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