Nghiên cứu tổng hợp và tính chất của một số dẫn xuất 1 aryltetrazole và bis thiazolidin 4 on

ĐẠI HỌC QUỐC GIA HÀ NỘI
TRƯỜNG ĐẠI HỌC KHOA HỌC TỰ NHIÊN


NGUYỄN THỊ THANH MAI

NGHIÊN CỨU TỔNG HỢP VÀ TÍNH CHẤT
CỦA MỘT SỐ GLUCOPYRANOSYL THIOURE
CĨ CHỨA DỊ VỊNG PYRIMIDIN

LUẬN ÁN TIẾN SĨ HÓA HỌC

HÀ NỘI – 2010


ĐẠI HỌC QUỐC GIA HÀ NỘI
TRƯỜNG ĐẠI HỌC KHOA HỌC TỰ NHIÊN


NGUYỄN THỊ THANH MAI

NGHIÊN CỨU TỔNG HỢP VÀ TÍNH CHẤT
CỦA MỘT SỐ GLUCOPYRANOSYL THIOURE
CĨ CHỨA DỊ VỊNG PYRIMIDIN
Chun ngành: Hóa Hữu cơ
Mã số: 62.44.27.01

LUẬN ÁN TIẾN SĨ HĨA HỌC

NGƯỜI HƯỚNG DẪN KHOA HỌC:
PGS. TS.NGUYỄN ĐÌNH THÀNH

HÀ NỘI – 2010

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MỤC LỤC
MỞ ĐẦU .............................................................................................................................................. 1
CHƯƠNG 1. TỔNG QUAN ................................................................................................................. 2
1.2. TỔNG QUAN VỀ THIOURE ....................................................................................................... 2
1.2.1. Cấu trúc và các liên kết trong phân tử [46,55] ......................................................................... 2
1.2.2. Tính chất của thioure ............................................................................................................... 2
1.2.3. Ứng dụng của thioure ............................................................................................................... 5
1.2.4. Phương pháp điều chế của dẫn xuất thioure ........................................................................... 7
1.3. TỔNG QUAN VỀ GLUCOSYL ISOTHIOXYANAT ................................................................... 13
1.3.1. Giới thiệu về glucosyl isothioxyanat ....................................................................................... 13
1.3.2. Tính chất hố học của glycosyl isothioxyanat[70,71,83,84] .................................................. 13
1.3.3. Phương pháp tổng hợp glycosyl isoxyanat và glucosyl isothioxyanat [83,101] ..................... 15
1.3. TỔNG QUAN VỀ DỊ VÒNG PYRIMIDIN................................................................................... 17
1.3.1. Tổng hợp vịng pyrimidin ........................................................................................................ 17
1.3.2. Tính chất của pyrimidin [7,9,86,96] ........................................................................................ 20
1.4. ỨNG DỤNG LỊ VI SĨNG TRONG HOÁ HỌC CACBOHYDRAT [14,56,75,88] .................... 22
1.5 MỐI LIÊN QUAN GIỮA CẤU TRÚC HÓA HỌCVÀTÁC DỤNG SINH HỌC ............................ 25
CHƯƠNG 2. THỰC NGHIỆM ...........................................................................................................30
2.1. TỔNG HỢP MỘT SỐ XETON α,β-KHÔNG NO ....................................................................... 32
1. 1,3-Diphenylprop-2-en-1-on (hay benzylidenaxetophenon) (3a1) ............................................... 33
2. 3-(4’-Fluorophenyl)-1-phenylprop-2-en-1-on [hay (4’-fluorobenzyliden)-axetophenon] (3b1) ..... 33
3. 3-(4’-Clorophenyl)-1-phenylprop-2-en-1-on [hay (4’-clorobenzyliden)-axetophenon] (3c1) ........ 33
4. 3-(3’-Clorophenyl)-1-phenylprop-2-en-1-on [hay (3’-clorobenzyliden)-axetophenon] (3d1) ........ 33
5. 3-(4’-Bromophenyl)-1-phenylprop-2-en-1-on [hay (4’-bromobenzyliden)-axetophenon] (3f1) ..... 33

6. 3-(4’-Metylphenyl)-1-phenylprop-2-en-1-on [hay (4-metylbenzyliden)-axetophenon] (3g1) .......... 33
8. 3-(3’-Metoxyphenyl)-1-phenylprop-2-en-1-on [hay (3’-metoxybenzyl-iden)axetophenon] (3j1) ... 34
9. 3-(3’,4’-Dioxymetylenphenyl)-1-phenylprop-2-en-1-on [hay (3’,4’-dioxymetylenbenzyliden)axetophenon] (3l1) ............................................................................................ 34
10. 3-(4’-Hydroxyphenyl)-1-phenylprop-2-en-1-on [hay (4’-hydroxy-benzyliden)axetophenon] (3m1)34
11. 3-(3’-Hydroxyphenyl)-1-phenylprop-2-en-1-on [hay (3’-hydroxy-benzyliden)axetophenon] (3n1)34
12. 3-(2’-Hydroxyphenyl)-1-phenylprop-2-en-1-on [hay (2’-hydroxy-benzyliden)axetophenon] (3o1)34
13. 3-[4’-(Dimetylamino)phenyl]-1-phenylprop-2-en-1-on [hay (4’-dimetylaminobenzyliden)axetophenon] (3p1) .............................................................................................. 34
15. 3-(4’-Clorophenyl)-1-(4-metoxyphenyl)prop-2-en-1-on [hay (4’-cloro-benzyliden)-4metoxyaxetophenon] (3c2) ............................................................................................................... 35

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16. 3-(3’-Clorophenyl)-1-(4”-metoxyphenyl)prop-2-en-1-on [hay (3’-cloro-benzyliden)-4metoxyaxetophenon] (3d2)............................................................................................................... 35
17. 3-(2’-Clorophenyl)-1-(4”-metoxyphenyl)prop-2-en-1-on [hay (2’-cloro-benzyliden)-4metoxyaxetophenon] (3e2)............................................................................................................... 35
18. 3-(4’-Bromophenyl)-1-(4”-metoxyphenyl)prop-2-en-1-on [hay (4’-brom-obenzyliden)-4metoxyaxetophenon] (3f2)................................................................................................................ 35
19. 1-(4’-Metoxyphenyl)-3-(4”-metylphenyl)prop-2-en-1-on [hay (4’-metylbenzyliden)-4metoxyaxetophenon] (3g2)............................................................................................................... 35
20. 1-(4’-Metoxyphenyl)-3- [4”-(propan-2-yl)phenyl]prop-2-en-1-on [hay (4’-isopropylbenzyliden)-4metoxyaxetophenon] (3h2)............................................................................................................... 35
22. 3-(3’-Metoxyphenyl)-1-(4”-metoxyphenyl)prop-2-en-1-on [hay (3’-metoxybenzyliden)-4metoxyaxetophenon] (3j2) ................................................................................................................ 36
23. 3- [4’-(Dimetylamino)phenyl]-1-(4”-metoxyphenyl)prop-2-en-1-on [hay (4’dimetylaminobenzyliden)-4-metoxyaxetophenon] (3p2) .................................................................. 36
24. 1-(4’-Bromophenyl)-3-(4”-fluorophenyl)prop-2-en-1-on [hay (4’-fluorobenzyliden)-4bromoaxetophenon] (3b3) ................................................................................................................ 36
25. 1-(4’-Bromophenyl)-3-(4”-clorophenyl)prop-2-en-1-on [hay (4’-clorobenzyliden)-4bromoaxetophenon] (3c3) ................................................................................................................ 36
26. 1-(4’-Bromophenyl)-3-(3”-clorophenyl)prop-2-en-1-on [hay (3’-clorobenzyliden)-4bromoaxetophenon] (3d3) ................................................................................................................ 36
27. 1-(4’-Bromophenyl)-3-(2”-clorophenyl)prop-2-en-1-on [hay (2’-clorobenzyliden)-4bromoaxetophenon] (3e3) ................................................................................................................ 36
29. 1-(4’-Bromophenyl)-3-(4”-metylphenyl)prop-2-en-1-on [hay (4-metylbenzyliden)4bromoaxetophenon] (3g3) ................................................................................................................ 37
30. 1-(4’-Bromophenyl)-3- [4”-(propan-2-yl)phenyl]prop-2-en-1-on [hay (4’-isopropylbenzyliden)-4bromoaxetophenon] (3h3) ................................................................................................................ 37
31. 1-(4’-Bromophenyl)-3-(4”-metoxyphenyl)prop-2-en-1-on [hay (4’-metoxybenzyliden)-4bromoaxetophenon] (3i3) ................................................................................................................. 37
32. 1-(4’-Bromophenyl)-3-(3”-metoxyphenyl)prop-2-en-1-on [hay (3’-metoxybenzyliden)-4bromoaxetophenon] (3j3) ................................................................................................................. 37
33. 1-(4’-Bromophenyl)-3-(2”-metoxyphenyl)prop-2-en-1-on [hay (2’-metoxybenzyliden)-4bromoaxetophenon] (3k3) ................................................................................................................ 37
34. 1-(4’-Bromophenyl)-3- [4”-(dimetylamino)phenyl]prop-2-en-1-on [hay (4’dimetylaminobenzyliden)-4-bromoaxetophenon] (3p3) .................................................................... 37
A-Phương pháp đun hồi lưu truyền thống (QTA1) ........................................................................... 37

B-Phương pháp sử dụng lị vi sóng (QTA2) ..................................................................................... 38
1. 2-Amino-4,6-diphenylpyrimidin (4a1) ........................................................................................... 39
2. 2-Amino-4-phenyl-6-(4”-fluorophenyl)pyrimidin (4b1). ................................................................. 39

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3. 2-Amino-4-phenyl-6-(4”-clorophenyl)pyrimidin (4c1). .................................................................. 39
4. 2-Amino-4-phenyl-6-(3”-clorophenyl)pyrimidin (4d1) ................................................................... 39
5. 2-Amino-4-phenyl-6-(4”-bromophenyl)pyrimidin (4f1) .................................................................. 39
7. 2-Amino-4-phenyl-6-(4”-metoxyphenyl)pyrimidin (4i1) ................................................................. 40
8. 2-Amino-4-phenyl-6-(3”-metoxyphenyl)pyrimidin (4j1) ................................................................. 40
9. 2-Amino-4-phenyl-6-(3”,4”-dioxymetylenphenyl)pyrimidin (4l1) ................................................... 40
10. 2-Amino-4-phenyl-6-(4”-hydroxyphenyl)pyrimidin (4m1) ........................................................... 40
11. 2-Amino-4-phenyl-6-(3”-hydroxyphenyl)pyrimidin (4n1) ............................................................ 40
13. 2-Amino-4-phenyl-6-(4”-dimetylaminophenyl)pyrimidin (4p1) .................................................... 41
14. 2-Amino-4-(4’-metoxyphenyl)-6-(4”- fluorophenyl)-pyrimidin (4b2) ............................................ 41
15. 2-Amino-4-(4’-metoxyphenyl)-6-(4”-clorophenyl)pyrimidin (4c2) ............................................... 41
16. 2-Amino-4-(4’-metoxyphenyl)-6-(3”-clorophenyl)-pyrimidin (4d2) .............................................. 41
17. 2-Amino-4-(4’-metoxyphenyl)-6-(2”-clorophenyl)-pyrimidin (4e2) .............................................. 41
19. 2-Amino-4-(4’-metoxyphenyl)-6-(4”-metylphenyl)-pyrimidin (4g2) ............................................. 42
20. 2-Amino-4-(4’-metoxyphenyl)-6-(4”- isopropylphenyl)-pyrimidin (4h2) ..................................... 42
21. 2-Amino-4,6-bis(4’-metoxyphenyl)pyrimidin (4i2) ...................................................................... 42
22. 2-Amino-4-(4’-metoxyphenyl)-6-(3”-metoxyphenyl)-pyrimidin (4j2) ........................................... 42
23. 2-Amino-4-(4’-metoxyphenyl)-6-(4”-dimetylaminophenyl)pyrimidin (4p2) .................................. 42
24. 2-Amino-4-(4’-bromophenyl)-6-(4”-fluorophenyl)pyrimidin (4b3) ............................................... 42
26. 2-Amino-4-(4’-bromophenyl)-6-(3”-clorophenyl)pyrimidin (4d3)................................................. 43
27. 2-Amino-4-(4’-bromophenyl)-6-(2”-clorophenyl)pyrimidin (4e3)................................................. 43
28. 2-Amino-4,6-bis(4’-bromophenyl)pyrimidin (4f3) ........................................................................ 43
29. 2-Amino-4-(4’-bromophenyl)-6-(4”-metylphenyl)-pyrimidin (4g3)............................................... 43

30. 2-Amino-4-(4’-bromophenyl)-6-(4”-isopropylphenyl)-pyrimidin (4h3) ......................................... 43
31. 2-Amino-4-(4’-bromophenyl)-6-(4”-metoxyphenyl)-pyrimidin (4i3) ............................................. 43
33. 2-Amino-4-(4’-bromophenyl)-6-(2”-metoxyphenyl)-pyrimidin (4k3) ............................................ 44
34. 2-Amino-4-(4’-bromophenyl)-6-(4”-dimetylaminophenyl)-pyrimidin (4p3) .................................. 44
35. 2-Amino-4-(4’-isopropylphenyl)-6-phenylpyrimidin (Phản ứng ‘one-pot’ từ 3 cấu tử) (4h1) ...... 44
2.3. TỔNG HỢP N-(2,3,4,6-TETRA-O-AXETYL-β-D-GLUCO-PYRANOSYL)-N’-(4’,6’DIARYLPYRIMIDIN-2’-YL)THIOURE .............................................................................................. 44
A-Phương pháp đun hồi lưu ............................................................................................................. 44
B-Phương pháp khơng dung mơi trong lị vi sóng ............................................................................ 44
1. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-(4’,6’-diphenylpyrimidin-2’-yl)thioure (6a1) ... 45
2. N-(2,3,4,6-tetra-O-axetyl--D-glucopyranosyl-N’-[4’-phenyl-6’-(4”’-flurophenyl)pyrimidin-2’yl]thioure (6b1) ................................................................................................................................. 45
3. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(4”’-clorophenyl)pyrimidin-2’yl]thioure (6c1) .................................................................................................................................. 45

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4. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(3”’-clorophenyl) pyrimidin-2’yl]thioure (6d1) ................................................................................................................................. 45
5. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(4”’-bromophenyl)pyrimidin-2’yl]thioure(6f1) ................................................................................................................................... 45
6. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(4”’-metylphenyl)pyrimidin-2’yl]thioure (6g1) ................................................................................................................................. 45
7. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(4”’-isopropylphenyl)pyrimidin-2’yl]thioure (6h1) ................................................................................................................................. 46
8. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(-4”’-metoxyphenyl) pyrimidin-2’yl]thioure (6i1) ................................................................................................................................... 46
9. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-phenyl-6’-(3”’- metoxyphenyl)pyrimidin-2’yl]thioure (6j1) ................................................................................................................................... 46
10. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-phenyl-6’-(2”’-hydroxyphenyl)pyrimidin2’-yl]thioure (6o1) ............................................................................................................................. 46
11. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-metoxyphenyl) - 6’-(4”’fluorophenyl)pyrimidin-2’-yl]thioure (6b2) ......................................................................................... 46
12. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-metoxyphenyl)- 6’-(4’”clorophenyl)pyrimidin-2’-yl]thioure (6c2) .......................................................................................... 46
13. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-metoxyphenyl)- 6’-(3’”clorophenyl)pyrimidin-2’-yl]thioure (6d2) .......................................................................................... 47
14. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-(4”-metoxyphenyl)- 6’-(2’”clorophenyl)pyrimidin-2’-yl]thioure (6e2) .......................................................................................... 47
15. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-metoxyphenyl) -6’-(4’”bromophenyl)pyrimidin-2’-yl]thioure (6f2) ......................................................................................... 47
16. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-metoxyphenyl)- 6’-(4’”metyphenyl)pyrimidin-2’-yl]thioure (6g2) .......................................................................................... 47
17. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-(4”-metoxyphenyl)-6’-(4’”-isopropylphenyl)pyrimidin-2’-yl]thioure (6h2) .................................................................................................. 47
18. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’,6’-bis(4”-metoxy-phenyl)pyrimidin-2’yl]thioure (6i2) ................................................................................................................................... 47

20. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-(4”-metoxyphenyl) 6’-(4’”-dimetylaminophenyl)pyrimidin-2’-yl]thioure (6p2) .................................................................................................. 48
21. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-[4’-(4”-bromophenyl)-6’-(4’”fluorophenyl)pyrimidin-2’-yl]thioure (6b3) ......................................................................................... 48
22. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-bromophenyl)-6’-(4’”clorophenyl)pyrimidin-2’-yl]thioure (6c3) .......................................................................................... 48

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23. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-bromophenyl) -6’-(3’”clorophenyl)pyrimidin-2’-yl]thioure (6d3) .......................................................................................... 48
25. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’,6’-bis(4”-bromo-phenyl)pyrimidin-2’yl]thioure (6f3) .................................................................................................................................. 49
26. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-bromophenyl) -6’-(4’”metylphenyl)pyrimidin-2’-yl]thioure (6g3) ......................................................................................... 49
27. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-bromophenyl) -6’-(4’”isopropylphenyl)pyrimidin-2’-yl]thioure (6h3) ................................................................................... 49
29. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4”-bromophenyl) -6’-(3’”metoxyphenyl)pyrimidin-2’-yl]thioure (6j3) ....................................................................................... 49
2.4. DEAXETYL HĨA CÁC DẪN XUẤT N-(2,3,4,6-TETRA-O-AXETYL-β-D-GLUOPYRANOSYL)N’-(4’,6’-DIARYLPYRIMIDIN-2’-YL)THIOURE................................................................................ 50
2.4.1. Hoạt hố nhựa trao đổi ion Wofatit KPS ................................................................................ 50
2.4.2. Deaxetyl hoá một số dẫn xuất N-(2,3,4,6-tetra-O-axetyl--D-glucoyranosyl)-N’-(4’,6’diarylpyrimidin-2’-yl)thioure .............................................................................................................. 50
1. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’-(4’,6’-diphenyl-pyrimidin-2’-yl)thioure (7a1) .. 50
3. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(3”-clorophenyl)-6’-phenylpyrimidin-2’yl]thioure (7d1) ................................................................................................................................. 51
4. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(4-bromophenyl)-6’-phenylpyrimidin-2’yl]thioure (7f1) .................................................................................................................................. 51
5. N-(2,3,4,6-Tetra-O-axetyl--D-glucopyranosyl)-N’- [4’-(-4”-metoxyphenyl) -6’-phenylpyrimidin-2’yl]thioure (7i1) ................................................................................................................................... 51
2.5. TỔNG HỢP 2-IMINOTHIAZOLIDIN-4-ON .............................................................................. 51
1. (Z)-2- [4”- phenyl-6’’-(4’”-Fluorophenyl)pyrimidin]-2”-ylimino)-3-(2’,3’,4’, 6’-tetra-O-axetyl-β-Dglucopyranosyl)thiazolidin-4-on (8b1) và (Z)-3- [4”-(4’”-fluorophenyl)-6”-phenylpyrimidin]-2”-yl)-2(2’,3’,4’,6’-tetra-O-axetyl-β-D-glucopyranosyl-1’-imino)thiazolidin-4-on (8b1 và 8’b1) ..................... 51
5. (Z)-2-[4”-phenyl-6”-(2’”’-Hydroxyphenyl)pyrimidin]-2”-ylimino)-3-(2’,3’, 4’,6’-tetra-O-axetyl-β-Dgluco-pyranosyl)thiazolidin-4-on và (Z)-3-[4”-(2’”-hydroxyphenyl)-6”-phenylpyrimidin]-2”-yl)-3(2’,3’,4’,6’-tetra-O-axetyl-β-D-gluco-pyranosyl-1’-imino)thiazolidin-4-on (8o1 và 8’o1) ................... 52
8. (Z)-2-[4”-(4’”- bromophenyl)-6”-(4””-Dimetylaminophenyl) ........................................................... 53
pyrimidin]-2”-ylimino)-3-(2’,3’,4’,6’-tetra-O-axetyl-β-D-gluco-pyranosyl)thiazolidin-4-on và (Z)-3- [4”(4’”-dimetylaminophenyl)-6”-(4””-bromophenyl)pyrimidin]-2”-ylimino)-3-(2’,3’,4’,6’-tetra-O-axetyl-βD-gluco-pyranosyl)thiazolidin-4-on (8p3 và 8’p3) ............................................................................ 53
2.6. HOẠT TÍNH SINH HỌC CỦA DẪN XUẤT 2-AMINO-4,6-DIARYLPYRIMIDIN VÀ CÁC HỢP
CHẤT THIOURE TƯƠNG ỨNG ...................................................................................................... 53
2.6.1. Các chủng khuẩn và nấm dùng thử nghiệm. ......................................................................... 53
2.6.3. Phương pháp thử ................................................................................................................... 54
1. Nguyên tắc ................................................................................................................................... 54

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Chương 3. KẾT QUẢ VÀ THẢO LUẬN ...........................................................................................55
3.1. TỔNG HỢP CÁC XETON α,β-KHÔNG NO ............................................................................. 55
3.2. TỔNG HỢP CÁC 2-AMINO-4,6-DIARYLPYRIMIDIN…………………………………………... 58
3.2.2. Phổ IR .................................................................................................................................... 71
1

3.2.3. Phổ H-NMR ........................................................................................................................... 71
3.2.3. Phổ MS ................................................................................................................................... 75
3.3 TỔNG HỢP CÁC N-(2,3,4,6-TETRA-O-AXETYL--D-GLUCOPYRANOSYL)-N’-(4’,6’DIARYLPYRIMIDIN-2’-YL)THIOURE .............................................................................................. 77
3.3.1. Tổng hợp N-(2,3,4,6-tetra-O-axetyl--D-glucopyranosyl)-N’-(4’,6’-diarylpyrimidin-2’yl)thioure. .......................................................................................................................................... 77
3.3.2. Phổ IR .................................................................................................................................... 78
3.3.3. Phổ NMR ................................................................................................................................ 83
3.3.4. Phổ MS ................................................................................................................................. 105
3.4. VỀ PHẢN ỨNG DEAXETYL HÓA MỘT SỐ HỢP CHẤT N-(2,3,4,6-TETRA-O-β-DGLUCOPYRANOSYL)-N’-(4’,6’-DIARYLPYRIMIDIN-2’-YL)THIOURE ....................................... 110
3.5. VỀ TỔNG HỢP MỘT SỐ DẪN XUẤT 2-IMINOTHIAZOLIDIN-4-ON..................................... 112
3.6. HOẠT TÍNH SINH HỌC CỦA DẪN XUẤT 2-AMINO-4,6-DIARYLPYRIMIDIN VÀ CÁC HỢP
CHẤT THIOURE TƯƠNG ỨNG .................................................................................................... 132
KẾT LUẬN……………………………………………………………………………………………… 139
DANH MỤC CÁC CƠNG TRÌNH LIÊN QUAN ĐẾN LUẬN ÁN…………………………………….140
TÀI LIỆU THAM KHẢO ..................................................................................................................142

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