• N g h i e n CLFU - K y thuat<br />
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N g h i e n c i r u t o n g h o p v a t h a m d o t a c d u n g<br />
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s i n h h o c c u a 5 - ( 2 ' - c l o r o b e n z y l i d e n ) r h o d a n i n<br />
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v a m o t so d a n c h a t b a s e M a n n i c h<br />
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Dinh Thj Thanh Hai, Tran Ngoc Bao Chau<br />
Bo mdn Hoa Huu co - Trudng Dai hoc Duoc Ha Noi<br />
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D a t v a n de thu tac dung sinh hpc cua mpt so din chit cua<br />
Rhodanin (2-thioxo-4-thiazolidinon) va cac rhodanin. Tiip tuc va phat then hudng nghien<br />
din chit da duoc nhieu nha khoa hpc nghien cuu v i cac din chat cua rhodanin, trong bai bao<br />
ciru ve tong hpp hda hpc va tac dung sinh hpc. nay, chung tdi trinh bay kit qua tong hpp va thu<br />
Cac cdng trinh nghien cuu cua cac tac gia trong hoat tinh khang khuin, khang nim, khang t l<br />
va ngoai nude da cong bo cho thiy cac din bao ung thu cua 5-(2'-clorobenzyliden)rhodanin<br />
chit rhodanin c6 hoat tinh sinh hpc da dang nhu va din chit base Mannich cua nd.<br />
khang khuin, khang nim, chong ung thu, khang Ket q u a v a b a n l u a n<br />
virus [1-7| Tong hpp hda hpc<br />
Trong cac th6ng bao trudc day ' , chung 1 1 4 l<br />
Cac din chit cua rhodanin dupe tong hpp<br />
tdi da trinh bay kit qua nghien cuu tong hpp va theo so do phan ung sau day:<br />
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CHO CI •NH N — CH — NR,R<br />
•NH<br />
2 2<br />
<br />
+ HCHO • HNR|R<br />
CH<br />
2<br />
<br />
Q<br />
s -s<br />
Rhodanin (1)<br />
Vdi:<br />
Chat -NR1R2 Chat -NR1R2 Chat -NRiR2<br />
<br />
<br />
r \<br />
2 5 - H N<br />
- •<br />
Tong hop 5-(2'-clorobenzyliden)rhodanin (1) Tong hop cac dan chat base Mannich (2 -10)<br />
Tong hpp 5-(2'-clorobenzyliden)rhodanin Tong hpp cac din chit base Mannich cua 5-<br />
(chit 1) bing phan ung ngung tu cua 2- (2'-clorobenzyliden)hydantoin (2-10) bing phan<br />
clorobenzaldehyd vdi rhodanin trong dung moi ung cua chit (1) vdi formol va cac amin<br />
acid acetic bang, xuc tac natri acetat khan, nhiet (morpholin, piperidin, toluidin, p-fluoroanilin, p-<br />
d§ phan ung 117 - 121°C. Phan ung dupe theo cloroanilin, N-methylpiperazin, dimethylamin, m-<br />
ddi bing sic ky Idp mong (SKLM) de xac dinh nitroanilin, p-iodoanilin) trong dung moi ethanol,<br />
thdi gian phan ung thich hpp. Kit qua la d i nhi$t d6 phan ung 60 - 65°C. Cac phan ung<br />
tong hpp dupe din chit ngung tu cua 2- dupe theo doi bing SKLM de xac djnh thdi gian<br />
clorobenzaldehyd vdi rhodanin (chit 1), hieu phan ung thich hpp. Kit qua la da tong hpp<br />
suit va m6t so hing so vat ly cua san pham dupe 9 dan chit base Mannich (2-10) vdi dac<br />
dupe ghi d bang 1. so \\&u ghi d bang 1.<br />
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24 TAP CHI DUQC HQC - 10/2010 (SO 414 NAM 50)<br />
• N g h i e n CLPU - K y thuat<br />
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Bang 1: Kit qua ting hap cac chit 1 -10<br />
Thai gian Nhi?t do Dung moi Diem chay Hieu suit<br />
Chat CTPT KLPT phan Ung phan Ung ket tinh lai<br />
CO (°C) (%)<br />
(gid)<br />
1 C H ONS CI<br />
10 255<br />
6 7,5 117-121<br />
2<br />
DMF: Aceton (1:1) 186-188 93,2<br />
2 C15H15O2N2S2CI 354 2 60 Ethanol 139-141 65,2<br />
3 Ci H ON S2CI 352<br />
6 17 22 60 Ethanol 96-98 51,0<br />
4 CieH ON S2CI 37415 2,5<br />
2<br />
65 Ethanol: CHCI (2:1) 3 135-137 58,8<br />
5 Ci7Hi ON S CIF 378 2 2,5<br />
2 65<br />
2 Ethanol: CHCI (2:1)<br />
3 144- 146 63,1<br />
6 Ci Hi ON S CI 396<br />
7 2 2,5 2 65 2 2 Ethanol: CHCI (2:1) 3 131 - 133 65,2<br />
7 Ci HieON S CI 367<br />
6 2.5 3 65 2 Ethanol: CHCI (2:1) 3 136-138 52,4<br />
8 C Hi ON S CI 312<br />
13 3 2 2 60 2 Ethanol 123-125 56,0<br />
9 Ci H 0 N S CI 392<br />
7 12 3 2.5 2 65 2 Ethanol: CHCI (2:1) 3 138-140 61,3<br />
10 Ci H ON S CII 486<br />
7 12 2,5<br />
2 65<br />
2 Ethanol: CHCI (2:1) 3 130-133 52,7<br />
06 tinh khiet cua cac chat tong hop duac da 1435cm' ) va dai hip thy cua nh6m >C=S cua nhan<br />
1<br />
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dugc so bp kiem tra bing do nhiet dp nong rhodanin trong vung (1240 - 1235cm" ). Pho IR cua<br />
1<br />
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chay va SKLM. Cau true cua 10 chat (1 - 10) chit 1 c6 dai hip thu -NH amid cua nhan rhodanin<br />
dupe xac nhan qua phan tich pho IR, MS, H - 1<br />
(3069cm" ), trong khi d6 cac din chit base Mannich<br />
1<br />
<br />
<br />
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NMR , C-NMR . Ket qua phan tich pho dupe<br />
13<br />
cua n6 khong 06 dai hip thu -NH amid va xuit hi$n<br />
trinh bay 0 bang 2, bang 3 va bang 4. dai hip thu cua nh6m CH trong cac vung (2945 -<br />
2<br />
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Pho IR cua 10 chat diu co dai hap thu dac 2921cm" va 2864 - 2833cm" ). Pho IR cua 5 chit<br />
1 1<br />
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trung cho dao dpng h6a tri cua nh6m >C=0 trong (4, 5, 6, 9, 10) c6 dai hip thu -NH cua hpp phan<br />
vung (1734 - 1701cm" ), lien ket C=C ethylenic la 1<br />
amin tham su dung ban diu la amin bac nhit.<br />
lien ket dupe tao ra sau phan ung ngung tu trong Pho khoi lupng cua 10 chit tong hpp dupe<br />
vung (1625 - 1594cm" ) deu xuat hien trong pho IR 1<br />
co pic phan tu phu hpp vcVi cong thuc du kiin<br />
cua chat ngung tu va cac din chit base Mannich va tuan theo "quy t i c nito", tren pho do MS c6<br />
tong hpp dupe, dai hip thu cua lien kit C m C cac pic cua cac ion manh dac trung phu hpp vd\<br />
tham trong cac vung (1603 - 1584cm" , 1452 - 1<br />
sa do phan manh.<br />
Bang 2: S6 li&u phi IR va MS cua cac chit tinghap duac<br />
Pho IR (KBr),cm' 1<br />
Pho khoi<br />
Chat<br />
VH vCH v =o N v =c Vc— c 2 c c vc=s Vc-Cl (NT)<br />
1 1734 1594 1594 1070 255<br />
3069 1239<br />
1435<br />
2 2945 1599 354<br />
1714 1599 1240 1051<br />
2864 1450<br />
3 2935 1595 1078 352<br />
1702 1595 1236<br />
2851 1439<br />
4 2921 1594 374<br />
3389 1701 1615 1236 1058<br />
2858 1436<br />
5 2925 1584 1058 378<br />
3424 1703 1614 1238<br />
2854 1437<br />
6 2926 .1585 1062 396<br />
3415 1711 1600 1235<br />
2852 1448<br />
2926 1594 1237 1077 367<br />
7 1702 1594<br />
2833 1438<br />
8 2852 1584 1066 312<br />
1717 1598 1235<br />
1442<br />
9 3405 2925 1592<br />
1713 1625 1238 1072 406<br />
2853 1452<br />
10 3427 2925 1603<br />
1705 1603 1240 1084 486<br />
2857 1436<br />
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TAP CHI DUQC HQC - 10/2010 (SO 414 NAM 50) 25<br />
• N g h i e n CLFU - K y thuat<br />
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Chung toi da phan tich pho H-NMR cua 10 diu xuit hien pic co dp chuyen djch hoa hpc<br />
1<br />
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chat tong hpp dupe va pho C-NMR cua chat 1 13<br />
trong vung 5 = 4,91 - 5,52ppm cua cac proton<br />
va chat 2. Kit qua phan tich pho H-NMR cho 1<br />
cua hpp phin aminomethyl (-CH -N
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