u tng ht s 4-
acetylsydnone tetra-O-acetyl--D-
galactopyranosyl thiosemicarbazon th  H i hc Khoa hc T 
Lu ThS.  ; : 60 44 27
ng dn: PGS.TS. Nguy
o v: 2012 Abstract. Tng hp cht 3-(R-  


 -(R-  -nitroso-N-(R-  ng.
Chuyp cht 4-acetyl-3-(R-n xut 4-bromacetyl-3-
(R-ng. Tng hp cht 2--(tetra-O-acetyl-
-D-galactopyranosyl-amino)]-5--arylsydnone)-6H-1,3,4-  u
c  h c  p cht 2--(tetra-O-acetyl--D-
galactopyranosylamino)]-5--arylsydnone)-6H-1,3,4-
sinh hc cng hc.

Keywords. ; Hp cht h; Hoc Content
p cht u hoc bit
 c th-thiadiazin  ho




. 
 



-carbon(C
4

  

C
4
- 

~1730cm
1

O
N
N
O
Ph
O
N
N
O
Ph

+0.01
+0.35
-0.14
+0.3
2 3
4
5

Hình 1.1. Biểu diễn điện tích trong vòng sydnone.
-
3




3

4

4,
O
1,
O
6

5

 
3


N-CN
PhCN
9

1-(Benzensulfonyl)-3-phenylnaphtho[2,3-e]1,3,4-thiadiazin-5,10-diol (10)   
-(benzensulfonyl)-3-phenyl-1H-benzo[f]indazole-4,9-un

N
N
S
O
O
SO
2
Ph
Ph
O
O
N
N
SO
2
Ph
Ph
t°, toluen
-S
10
11

1,3,4-thiadiazin    (20)  

2
R
3
H
+
-S
20
21

     - -3-methyl-2,3-dihydro-6H-1,3,4-thiadiazin(22)
(23)
     -phenyl-  -ethoxycarbonyl-6H-1,3,4-thiadiazin(20)
(R
2

H-1,3,4-thiadiazin
-40% 5-imino-1,2-


N
N
S
Ph
NR
Me N
N
Ph
NHR
Me
H

N
H
S
HOOC
NPh
Ph
N
H
N
HOOC
NHPh
26
27
PPA
-S
N
N
N
H
N
H
O
O
Ph
PhN NPh
Ph
28

      -thiadiazin       -
         -thiadiazin   


  -nitrobenzaldehyd (R
2
=H, NO
2
 
acid, thu  -(benzylideN-  -[(4-nitrobenzylidene)hydrazino]thiazole
(32).
NH
N
S NH
2
+
R
1
H
CH
3
31
N
S
CH
3
NH
2
NH
R
1
N
CH

1
34
Mel, Me
2
CO
t°, 10h

2-Dialkylamino-5-aryl-6H-1,3,4-thiadiazin
1,3,4-thiadiazin        -dialkylamino-6H-1,3,4-
thiadiazin            dimethyl sulfoxide
-pyrrolidino- -cyclohexylamino-5-phenyl-6H-1,3,4-thiadiazin
-dialkylamino-
5-phenyl-6H-1,3,4-thiadiazin
N
N
S
Ph
R
1
N
N
+
S
Ph
R
1
R
2
35
X

N
S
R
2
R
1
36
ButOCl,DMF, 0 °C
-CO
2

 6H-1,3,4-thiadiazin-2-amin (37) -halogen keton cho 2H-
imidazo[2,1-b]6H-1,3,4-thiadiazin(38) (R
1
=Ar; R
2
=H).
N
N
S
Ph
NH
2
+
R
2
Br
O
R
1

NH
NHAc
N
S
MeCOOC
Ph
NH
NH
2
N
S
MeCOOC
Ph
NH
N
CH
3
CH
3
N
N
S
MeOOC
Ph
NH
2
HCl
Me
2
CO

 

2


2
, phm 1956[21]. 
-mercapto-1,3,4-thiadiazol. Ph
sau:



 DMF, d




  

 
               


              

       

 




  -        -acetyl-3-(R-phenyl)sydnone  
percloric HClO
4
510C.
- bromo

N-(R-phenyl)glycine
N-(R-phenyl)glycine em N-
 
Phương pháp 1:N-(R-phenyl)



 N-(R-phenyl)glycine
 
 N-(R-phenyl)glycine.
Phương pháp 2;





Phương pháp 3:            


N-(R-phenyl)glycine
N-nitroso-N-(R-phenyl)glycine
N-nitroso-N-(R-phenyl)glycine
N-(R-phenyl)glycine 

5
   

 acetic 


m 96
0

Phương pháp lạnh
10
4

 
15
30-

em 

   
2
O
5

c 


dunn-hexan : ethy
-bromoacetyl-3-(R-phenyl)sydnone
           bromo   












 



, 


. 



  




2






 
o

 
n-hexan 
        2-3     
 


.4.

Bảng kết quả tổng hợp và dữ kiện vật lý của 2-(2’,3’,4’,6’-(tetra-O-acetyl-β-D-
galactopyranosylamino)-5-(3”-arylsydnone)-6H-1,3,4-thiadiazin
N
R
Màu sắc
Hiệu suất(%)
Đ
nc
(°C)
7a
H

75
107,2-108,1
7b
4-Me

,3
’
,4
’
,6
’
-tetra-O-acetyl-β-D-galactopyranosylamino)-5-[3
’’
-(4-
bromophenyl)sydnone]-6H-1,3,4-thiadiazin.

Bảng băng sóng hấp phụ phổ IR của các hợp chất2-(2
’
,3
’
,4
’
,6
’
-tetra-O-acetyl-β-
D-galactopyranosylamino)-5-(3
’’
-arylsydnone)-6H-1,3,4-thiadiazin
N
0

R

NH


1747
1227, 1056
1573, 1498
1600
7d
-MeO
3324
1744
1223, 1059
1515, 1490
1605
7e
4

-Cl
3479
1746
1231, 1056
1577, 1500
1600
7f
4

-Br
3376
1745
1229, 1060
1571, 1500
1600
- Phổ

135,5--4 -5 
104,7-104,3. 
-61,6ppm. Ba carbon C-5, C---thiadiazin 
   -     
3
    
(CH
3
CO) n--

- Phổ 2D-NMR: COSY, HMBC, HSQC
-NMR: 1,3,4-thiadiazin
7f
1
H NMR 
13
C NMR 
   2-(2

,3

,4

,6

-tetra-O-acetyl--D-galactopyranosylamino)-5-(3

-arylsydnone)-
6H-1,3,4-thiadiazin7a-f.


H--6b (3,60)
 
-2(=168.9 ppm)
-6a (=3.72 ppm) -6b ((=3.60 ppm)
  -        -6a (=3.72 ppm)  -6b ((=3.60
ppm), 





 ppm) 





-3-5 ppm).

1
H-
13
C -5

-
roton H- (=4,02- H-=5,24 
1
H-
13
C  


+



V th hom: nh hoc cthiadiazin
b nghi c ch
ti thing 96 mit th nghim bao g
chng: Vi khun gram (-):Vi khun gram (+):Nm si; Nm men
Kt qu c ch ra  bng sau:

Bảng 3.5.1. Kết quả thử hoạt tính kháng khuẩn và kháng nấm của thiadiazin
Kí
hiệu
mẫu
Nhóm thế R
Nồng độ ức chế tối thiểu MIC, µg/ml
Vi khuẩn
gram(-)
Vi khuẩn
gram(+)
Nấm mốc
Nấm men
E. coli
P. aer
B. sub
S. aur
A.nig
F.oxy
S.cer

25
7c
2-Me
-
-
-
100
100
-
-
-
7d
4-OMe
-
-
100
-
-
-
-
-
7e
4-Cl
100
-
100
-
-
-
-




N-nitroso-N-(R-phenyl)glycine
- -arylsydnone.
  -           -acetyl-3-

2
O
5

-bromoacetyl-3-

2 --(tetra-O-acetyl--D-galactopyranosyl amino)-5-
-arylsydnone)-6H-1,3,4-    -(tetra-O-acetyl--D-
-bromoacetyl-3-

3. 
1
H NMR,
13
CNMR,

4.          
Gram-(-) Escherichia coli Pseudomolas aeruginosa   -(+) Bacillus
subtillisStaphylococcus aureusAspergillus niger Fusarium oxysporum
men Candida albicansSaccharomyces cerisiae
t 7b 7f 




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