الفهرس 
Chapter 1 IntroductionOnly 14 pages are availabe for public view
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Abstract
P-chlorobenzaldehyde and ethylcyanoacetate was heated under
reflux to afford ethyl (Z)-3-(4-chlorophenyl)-2-cyanoacrylate (1) as a white
powder in 85% yield.
Ethylcyanoacetate and hydrazine hydrate was reacted to afford
cyanoacid hydrazide (2) as a white powder in 77% yield.
Cyanoacid hydrazide (2) with D-glucose or D-xylose or D-galactose
was heated under reflux to afford 2-cyano-N’-[(2S,3R,4R,5R,E)-2,3,4,5,6-
pentahydroxyhexylidene]acetohydrazide (3a), 2-cyano-N’-[(2S,3S,4S,E)-
2,3,4,5-tetrahydroxy pentylidene]aceto hydrazide (3b) and 2-cyano-N’-
[(2S,3R,4S,5R,E)-2,3,4,5,6-penta hydroxyhexylidene]acetohydrazide (3c)
as a white powder in 83%, 85% and 83% respectively.
Compound (3a) or (3b) or (3c) with arylidine cyanoacetate (1) in
absolute ethanol was heated under reflux to afford ethyl 7-(4-
chlorophenyl)-6-cyano-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-penta
hydroxypentyl]-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate
(4a), ethyl 7-(4-chlorophenyl)-6-cyano-5-oxo-2-[(1S,2R,3R)-1,2,3,4-
tetrahydroxybutyl)-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-
carboxylate (4b) and ethyl 7-(4-chlorophenyl)-6-cyano-5-oxo-2-
[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl)-1,5-dihydro-[1,2,4]
triazolo[1,5-a]pyridine-8-carboxylate (4c) as a colourless powder in 83%,
82% and 83% respectively .
Compound (4a) or (4b) with hydrazine hydrate in absolute ethanol
was heated under reflux to afford ethyl 7-(4-chlorophenyl)-6-
(hydrazinyl(imino)methyl)-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-
pentahydroxypentyl]-1,5-dihydro-[1,2,4] triazolo[1,5-a]pyridine-8-
carboxylate (5a) and ethyl 7-(4-chlorophenyl)-6-(hydrazinyl
(imino)methyl)-5-oxo-2-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-1,5-
dihydro-[1,2,4]triazolo [1,5-a]pyridine-8-carboxylate (5b) as a colourless
powder in 83% yield.
Compound (5a) and malononitrile in absolute ethanol was heated
under reflux to afford ethyl 6-(6-amino-5-cyano-2,5-dihydro-1,2,4-triazin3-yl)-7-(4-chlorophenyl)-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-
pentahydroxypentyl]-1,5-dihydro-[1,2,4] triazolo[1,5-a]pyridine-8-
carboxylate (6) as a colorless powder in 78% yield.
Compound (6) and formamide was heated under reflux to afford
ethyl 6-(5-amino-2,4a-dihydropyrimido[5,4-e][1,2,4]triazin-3-yl)-7-(4-
chlorophenyl)-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-pentahydroxypentyl]-
1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (7) as a colorless
powder in 77% yield.
Compound (7) with carbon disulfide and potassium hydroxide as a
basic medium in absolute ethanol was heated under reflux to afford ethyl
7-(4-chlorophenyl)-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-pentahydroxy
pentyl]-6-(9-thioxo-9,10,10a,10b-tetrahydro-3H-[1,2,4] thiadiazolo
[2’,3’:1,6] pyrimido[5,4-e][1,2,4]triazin-2-yl)-1,5-dihydro-[1,2,4]triazolo
[1,5-a]pyridine-8-carboxylate (8) as a colorless powder in 76% yield.
Compound (7) and phenyl isothiocyanate in absolute ethanol was
heated under reflux to afford ethyl 7-(4-chlorophenyl)-5-oxo-2-
[(1S,2R,3R,4R)-1,2,3,4,5-penta hydroxypentyl]-6-[5-(3-phenylthio
ureido)-2,4a-dihydropyrimido[5,4-e] [1,2,4]triazin-3-yl]-1,5-dihydro-
[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (9) as a colorless powder in
78% yield.
Compound (9) with carbon disulfide and potassium hydroxide as a
basic medium in absolute ethanol was heated under reflux to afford ethyl
7-(4-chlorophenyl)-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-penta hydroxyl
pentyl]-6-(9-phenyl-8,10-dithioxo-8,9,10,11b-tetrahydro-3H-[1,3,5]
triazino [1’,2’:1,6] pyrimido[5,4-e][1,2,4]triazin-2-yl)-1,5-dihydro-
[1,2,4]triazolo [1,5-a]pyridine-8-carboxylate (10) as a colorless powder in
76% yield.
Compound (9) and ethyl methyl malonate in absolute ethanol was
heated under reflux to afford ethyl 7-(4-chlorophenyl)-6-[5-(4,6-dioxo-3-
phenyl-2-thioxotetrahydropyrimidin-1(2H)-yl)-2,4a-dihydropyrimido
[5,4-e][1,2,4] triazin-3-yl]-5-oxo-2-[(1S,2R,3R,4R)-1,2,3,4,5-penta
hydroxypentyl]-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate
(11) as a colorless powder in 76% yield.
Compound (5b) and ethyl methyl malonate in absolute ethanol was
heated under reflux to afford ethyl 6-(1-amino-4,6-dioxo-1,4,5,6-
tetrahydropyrimidin-2-yl)-7-(4-chlorophenyl) -5-oxo-2-[(1S,2R,3R)-
1,2,3,4-tetrahydroxybutyl]-1,5-dihydro- [1,2,4] triazolo[1,5-a] pyridine-8-
carboxylate (12) as a colorless powder in 78% yield.
Compound (12) and acetaldehyde in absolute ethanol was heated
under reflux to afford ethyl 6-[(E)-1-amino-5-ethylidene-4,6-dioxo1,4,5,6-tetrahydro pyrimidin-2-yl]-7-(4-chlorophenyl)-5-oxo-2-
[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-1,5-dihydro-[1,2,4]triazolo[1,5-
a]pyridine-8-carboxylate (13) as a colorless powder in 78% yield.
Compound (13) and hydrogen peroxide was heated under reflux to
afford ethyl 6-(7-amino-2-methyl-4,8-dioxo-1-oxa-5,7-diazaspiro
[2.5]oct-5-en-6-yl)-7-(4-chlorophenyl)-5-oxo-2-[(1S,2R,3R)-1,2,3,4-tetra
hydroxy butyl]-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate
(14) as a colorless powder in 76% yield.
Compound (14) and formamide was heated under reflux to afford
ethyl 6-(7-amino-2-methyl-4,8-dioxo-1,5,7-triazaspiro[2.5]oct-5-en-6-yl)-
7-(4-chlorophenyl)-5-oxo-2-[(1S,2R,3R)-1,2,3,4-tetrahydroxy butyl]-1,5-
dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (15) as a colorless
powder in 73% yield.
Compound (15) and dimethyl sulphate in dimethyl formamide was
heated under reflux to afford ethyl 6-(7-amino-1,2-dimethyl-4,8-dioxo1,5,7-triazaspiro[2.5]oct-5-en-6-yl)-7-(4-chlorophenyl)-5-oxo-2-
[(1S,2R,3R)-1,2,3,4-tetrahydroxy butyl]-1,5-dihydro-[1,2,4]triazolo[1,5-
a]pyridine-8-carboxylate (16) as a colorless powder in 70% yield.
Compound (4c) with ethyl choloroacetate and potassium carbonate
anhydrous in dimethyl formamide was heated under reflux to afford ethyl
7-(4-chlorophenyl)-6-cyano-1-(2-ethoxy-2-oxoethyl)-5-oxo-2-
[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1,5-dihydro- [1,2,4]
triazolo[1,5-a] pyridine-8-carboxylate (17) as a colorless powder in 86%
yield.
Compound (17) with thiocarbazide in methanol and sodium
methoxide solution was heated under reflux to afford ethyl 1-[(4-amino-5-
thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-7-(4-chlorophenyl)-6-
cyano-5-oxo-2-[(1S,2R,3S,4R)-1,2,3,4,5-penta hydroxypentyl]-1,5-
dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylate (18) as a colorless
powder in 80% yield.
Compound (18) and phthalic anhydride was fused in an oil bath to
afford ethyl 7-(4-chlorophenyl)-6-cyano-1-[(4-(1,3-dioxoisoindolin-2-yl)-
5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-5-oxo-2-
[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1,5-dihydro-[1,2,4]
triazolo[1,5-a]pyridine-8-carboxylate (19) as a colorless powder in 83%
yield.
Compound (18) with carbon disulfide and potassium hydroxide as a
basic medium in absolute ethanol was heated under reflux to afford ethyl
7-(4-chlorophenyl)-6-cyano-5-oxo-2-[(1S,2R,3S,4R)-1,2,3,4,5-
pentahydroxypentyl]-1-[(6-thioxo-5,6-dihydro-[1,2,4]triazolo[3,4-
b][1,3,4]thiadiazol-3-yl)methyl]-1,5-dihydro-[1,2,4]triazolo[1,5-
a]pyridine-8-carboxylate (20) as a colorless powder in 80% yield.
Compound (18) and D-xylose in absolute ethanol/ glacial acetic acid
was heated under reflux to afford ethyl 7-(4-chlorophenyl)-6-cyano-5-oxo2-[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1-[(4-[{(2S,3R,4R,Z)-
2,3,4,5-tetrahydroxy pentylidene}amino]-5-thioxo-4,5-dihydro-1H-1,2,4-
triazol-3-yl)methyl]-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine-8-
carboxylate (21) as a colorless powder in 85% yield.
Compound (18) and benzaldehyde in absolute ethanol was heated
under reflux to afford ethyl 1-[(4-[{(E)-benzylidene)amino}-5-thioxo-4,5-
dihydro-1H-1,2,4-triazol-3-yl]methyl]-7-(4-chlorophenyl)-6-cyano-5-
oxo-2-[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1,5-dihydro-[1,2,4]
triazolo[1,5-a]pyridine-8-carboxylate (22) as a colorless powder in 84%
yield.
Compound (18) with polyphosphoric acid and ethyl cyanoacetate
was fused in an oil bath to afford ethyl 7-(4-chlorophenyl)-6-cyano-1-[{6-
(2-ethoxy-2-oxoethyl)-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-3-
yl}methyl]-5-oxo-2-[(1S,2R,3S,4R)-1,2,3,4,5-pentahydroxypentyl]-1,5-
dihydro-[1,2,4]triazolo[1,5-a] pyridine-8-carboxylate (23) as a colorless
powder in 83% yield.
Compound (18) with ethyl choloroacetate and potassium carbonate
anhydrous in dimethyl formamide was heated under reflux to afford ethyl
1-[(4-amino-5-[(2-ethoxy-2-oxoethyl)thio]-4,5-dihydro-1H-1,2,4-triazol3-yl)methyl]-7-(4-chlorophenyl)-6-cyano-5-oxo-2-[(1S,2R,3S,4R)-
1,2,3,4,5-pentahydroxypentyl]-1,5-dihydro-[1,2,4]triazolo[1,5-a]pyridine8-carboxylate (24) as a colorless powder in 84% yield.
The new Derivatives that were prepared were tested in terms of their
biological activity as anti-cancer, anti-virus, anti-bacterial and antifungal agents, and the compounds demonstrated good biological
activity.