Tliymin lii hop chaL rat i)h6 bie'n Lrong tii Mau hoL ciic thuoc khiing HIV-AIDvS dang
iihiiMi. No lii thimh phim ca'u lao niai ciic axil thfdc Ung dung deu chiia di vong Lhymin nucleic - chat di truyen trong CO the smh viiL. nhu AZT. d,T... [1,2,3]. Trong noi dung Ngiiy nay. thymin dudc: ling dung rat riing cong trinh nay chung toi cong bo ket qua nli liini trung gian trong (lua trinh long hdp tong hdj) Thymin bang con dUdng thuan Igi cac hdp chat c6 boat tfnh sinh hoc nhii nhat lam nguyen lieu trung gian cho qua
khang khuan. khang nam, khang ung thvi ' trinh Long hdp c\;[' vii AZT. (Stavudin va
vi\ diic hii'l IA ciic lluuVc kliimg MIV - AIDS. Zinovudin). IL KET QUA VA THAO LUAN S(jf do plii'ui ling tong h(;p Thymin:
H O O C - C O O H -1^"^""^"' > K L O O C - C O O K L '^""'" > CH.CH.COOH CH.CHXOOKt 2)CH:,C00H COOLt CIM. CH COOEt (I) COOEt C=0 NaBH. CHOH CMC COOEt (II) Ure/Olcum
Ket qua n g h i e n cuTu k h o a h o c B a n g k e t q u a t h i / c n g h i e m : STT 1, 2 3 4 5 S a n p h a m Dietyl o x a l a t l^^tyl p t o p i o n a t E t y l e t o x a l y l p r o p i o n a t P-metyl m a l a t T h y m i n H a n g so v a t ly t,s = 99"C t s ^ IS.V'C t s = 114 - IIG'^C ( l O m m H g ) S;in pbiim Iho
Ir - 3 2 6 - 330"C H i e u s u a t H^V'n H'Vn 8 1 " . •10".
Phim lfng este hoa difOc thiic hien Lir ai^icol
vaaxiL cacboxylic v6i xue tiu: axit vo cO manh
H.,SO|. He n a n g eao hieu suiU. ciia qua t n n h , ancol diidc diing dU ga'p doi ket hop viJi ky
thuat liicli loai lufcJc bang dang phf voi dung moi beir/cn. Tuy nhien, qua trinh i;uh wvioc bting dimg phi diiOc thuc hien sau 10 gid klu
ma phim img da gan d a t thioc trang thai cim bang. Vdi phiidng |)hii]) niiy Ihiii gian phim
ling dLi{.fc riit ngan tu! 24 [;iu xuong cdn 15 gitJ do 10 gid dau nhiet do pluin ifng duy Lri 0 85"C. 5 gid sau nhiet do phi'm itnij; chi U 75"C tlie Iil Li-ong 10 gid d a u phan dng xiiy ra vdi toe-
do Idn luJn. Hieu s u a t cua pluin ring dat 84%. Pho hdng ngoai xuat hien pic C = 0 riiL dac
trUng. pic OH axit da ma't di [4].
Phim d n g ngiing lu giiia elyl i^i-opionat v6i dietyloxalat tao ra eLy]etoxalylj)ropionat (I) sii d u n g xiic tac C.H.ON^i va d u n g mdi eted nhiet do tu: 5-10**C. San phiim ra't de bi tach loai ( T ) , d n h i e t do tren 1 iiO^C ni'ii diioC
chirng ciil d 114- lliy'C ( l O m m l i g ) [C)\. Thd
hong ngoai xiutt hien pic v, .^ - ^'^'^d cm . Trong ciie cong trinh Irifdc day ciic Liic gi;i
thUc 'udn khii hoii e t y l e t o x a l y l p r o p i o n a t
Oil
I
.c.
N^ CFh
h a n g Liu: nhim Hidro vdi xuc lac Pt |(i|. Tuy nhien, ti-ong cdng I.iinh nii>' p h a n ifng khii hoil dLfoc LJuic hicn b a n g Liic nliim khii iau diu va chpn loc la Nal.-iH, Li'ong mdi Lriidng
kii'm \'ii dung mdi clanol - M.O o nluel dn 0-
.')"('. I 'hit hi Mi;; n|;oai iu;i s.iii pli.'iiii \u;il
hien \\ ,, 1739cm ', x',,,, = 3-1S0.7cm '.
i^him itn^i, (long vdng^ Lhymin diiOc Lluic
hii'u Lii etyleUixalylpropioiiat va uri' \'di xiic 'liic oleum (IdM. SO,) d nliicL dp 0(1 D . / V va
thdi gian 1.5 gid (7). San phiim d dang Linh
Die khdng miui, tan it trong luidc va co diem chiiy326"'C. hieu smVt 40%. (adsbygoogle = window.adsbygoogle || []).push({});
Ca'u t r u e cua Lhymin dudc xiic dinh
biing phiiong phiip IR. ' H - \ M R vi'i ^'C-
NMR. Pho hong ngoai cua Lhymin r-iit phu hdp vdi pho c h u a n . O t r a n g thiu Linh t h e do ton tai ciic lien koL ciui ludi'ij m'-n cac dao dong cua lien ket N'-M ciio pic clu'in rdng hdn \'a lim vdi ciie dao ddng cua cac
lien ke'l khiic. \\n - 3300cm '.
v., ii = dO(;2enV' , \ ' , , p 2931cm '. 2S50cm'. Hai dao dpng cua C = 0 cd cudng do Idn.
chim rpng \'ii ra't dac Lrung d 17 15cm' va
1077cm '. UU N' (Ille) O I 2 , C H N 13 o'' \Nir '^ 4 [Wh^} >
Ket qua n g h i e n cifu k h o a n o c
Tren phd ' H - N M R co cac pic s a u : 5 = lO.ySppm (s, I H ) dac trUng cho H '
5 = 10,57ppm (s, I H ) dac trirng cho H ' 5 = 7.25ppm (q. I H ) J = 15Hz dac triing 5 = 7.25ppm (q. I H ) J = 15Hz dac triing
cho H" va xuiil hi<>n LiiOng tiie k h o n g gian vdi Hidro t r o n g CH;,.
T r e n pho " C - N M R x u a t hien 5 pic dac
t r a n g vil ra't rd n e t S^i = IGoppnu o^:, =
I S l p p m , 6.:, = 138ppm. a^, = 108ppm. 5(., ^ l l , 8 p p m .
TCr c;'ir du- kicii phii IR.'H-NiVIU. ''(^ - N M R C h u n g Ld r i m g s a n pha'm t h y m i n
5 = l , 7 3 p p m (d,3H) J = 15Hz dac trUng diTdc t o n g hdp cd cau t r u e d u n g dir kien,
c^oH'. ^ do t i n h k h i e t cao dUa t r e n con d u d n g
Do vay dUa vao p h o ' H - N M R chiing td t a o n g doi t h u a n Idi tir cac n g u o n n g u y e n r^ng trong d u n g dich hdp c h a t ton tai d lieu ddn gian, s5n co tii' cdng nghie|> hoa d a n g ( H U . . . c h a t .
UL P H A N T H T / C N G H : ! ] : M
Pho hong ngoai dUdc do theo phiidng H.SO., dac 2,6ml (0,05mol). phap mau long t i n h k h i e t (cha't long) va ep
vien KHr (cha't I'iin) t r e n rniiy pho AVATA 360 - h a n g Nicolet (FT-IR). P h o 'H- NMR, '•^C - NMR dUdc do t r e n m a y 500MHz, dung mdi D M S O . Tong hc'p e t y l p r o p i o n a t : Hon h d p p h a n l i n g gom 3 7 m l a x i t propionic ( 0 , 5 m o l ) , 5 8 m l C J I ^ O H Vsp = 57ml: (ts = ISo'^C''^ 115"C'"; d = 1,08); hieu sua't = 84%,. T o n g hop e t y l e t o x a l y l p r o p i o n a t :
2,3g Na (O,lmol) dUdc cho vao binh chiia 50ml ete va nhd tiT tii 5,8ml C,H,OH (O,lmol) vao hon hdj) vii lam lanh den 0-5"C. Hdn hdp dietyl oxalat L3,5ml (O.lmol) va etyl ijro|)ionat 11,5ml (0,1 mol) diidc; nhd tir tit vao binli phan
(Imol); 2,()nil H;^SO, dAc ( 0 , 0 5 m o ] ) diidc ting va dvUk: khua'y trong 2 gid d nhiet do 5-
dun hdi lu'u 10 gid d 82*'C ( h e t h d n g cd bay tach nu'dc). S a u 10 gid, 4 5 m l b e n z e n
(n.rnnid) du*»,(e clu) s'ao hon lu,'p \':\ Lhiic
hien quii t r i n h loai luidc d e u k h i k h d n g con nirdc bi t a c h r a ( k h o a n g 5 gid nOa). Sau philn d n g ca't loai b e n / c n va e t a n o l , rila est(; b a n g niidc s a u dd biing NaHCO;, b a o b o a vii r d a lai b a n g midc, lam kho b i m g NavSO.,. s a n p h a m tinh khiet llui tliioV bAng c l u i n g ca't d 9 8 - 9 9 " C :
V --^ 48ml (d,-'" --= 0 . 8 9 . t s ; 9 9 " C ) ; h i e n
suiit - 84%..
Tong ho^p d i e t y l o x a l a t :
TiiiJng tl/ n l u i e t y l p r o p i o n a t . Sim pliiim (adsbygoogle = window.adsbygoogle || []).push({});
tinh khiti't diidc cat diidi ap s u a t giam d
70mmHg.
Axit oxalic 45g (0,5 mol ); (^,M,OM lUJml (2mol)
lO'^C. Sau pluin dng. them 10ml CM.COOH sau dd 50ml HvO vii chiet san pham bang
30mi etc. Cho ba\' hdi o\n vii cat du'('ii iip sua't lOmmHg Os - 111 110"Cj lhu dvuy sim
pham tmh khiet V = 15ml; hieu s'.-:Y! - 8]%>. Tong hg^p dietyl-p-metylmalat:
Hon hdp phim d n g gom 9,2ml (O.Oomol)
etyletoxaly-propionat; 15ml Cd \r,()\l vii 2ml N a O H 2N duoc liim lanh dC-n 0- 5**C.
Nhd Lir tir (id'c do 0.5ml/phut) d u n g dich NaBH,,(0.5g), 20ml N a O H 0,2N, khua'y vii gid n h i e t do d 0-5*'C. S a u p h a n dng, etanol diTdc loai bd b a n g c h u n g cat. sim j)ham diidc cliiet b a n g 50ml ete sau khi pha loang hdn hdjj bang* 50ml HvO. Loai bd ete b a n g chiing cat l h u diidc sim p h a m (ho V = 7,5ml k h o n g can tinh che mil d u n g ngay viio phim ling n g u n g tu sau.
18 HOA HOC V A Q N G DUNG-So 9-2003
Ket qua n g h i e n cijfu k h o a hoc T I E N - T h y m i n , DMSO, IH fj i\A V A - 1^.-^. Ml T I E N - T h y i n i n , DMSO, C13CPD Y
(Xfiii tiep (i (inti '2-)
HOI HOA HOC VIET NAM PHAN HOI HOA HUU CO PHAN HOI HOA HUU CO
Hoa ligc Huu ca vi su nghiep
Cong nghiep Iwa vd Hien dai hoa ddt nudc
TUYEN TAP CAC CONG TRINH HOI NGHI KHOA HOC VA CONG NGHE HOI NGHI KHOA HOC VA CONG NGHE
• • - •
HOA H Q U CO
HOI NGHI TOAN QUOC LAN THLf HAI
Hdi nghi Khoa hpc yii Cdnji nfjUc Hda Hilu co iudn quoc idn thu 2
f T 6 N G H O P , XAC DINH CAU TRUC VA THLT HOAT TINH
SINH HOC CUA M O T SO D A N X U A T T H ^ 6 VITRIsd 5 CUA 2-AMINO-l,3,4-THIADIAZOL VA l,2-DIAMINO-l^,4.TRIAZOL 2-AMINO-l,3,4-THIADIAZOL VA l,2-DIAMINO-l^,4.TRIAZOL
Synthesis, structural determination and biologicai activities of some 1 5-substitudd 2-amino-1,3,4-thiadiazol and 3.4-diamino-1,3,4-triazoi
i , Nguyin Dinh Triiu, Trdn Thi Phuang Thdo
Khoa Hod hqc-Dqi hpc Khoa hpc Tu Nhien-Dai hpc Qudc gia Hd Ndi
SUMMARY . •
Severaf derivatives of 2-amino-5-furyt-1 J.4'thiailiazol and 1,2-diamino-5-furyi-lJ.4- triazof have been syntt\esized and tested for their antimicohial and fungicidal activity. The stntttiues of the synthesized cnmpoumts have been estabhshed on tlie basis of their spectral data.
I.M6 DAU :
Tix Uu, cdc hap ch^t di vong noi chung da dugc bi^t den do nhung hoai lmh sinh
hpc ohong phu ciia chiing. Dac bi6t,v6ng 1,3,4-lhiadiazol v& l,3.4-tTia2ol cung da duoc (adsbygoogle = window.adsbygoogle || []).push({});
|nhi4u lac'gia nghi6n curu do cdc hoat tfnh khang khua'n v^ dac bidt U khk n5ng khdng ndm.
jM^t s6 dSn xua't cua v6ng l.3.4-thiadiazol co kha nang ch6ng b^nh hen xiiySn cho ngu&i,
b^nh 6 chim vh. ciru. Nguoi la cung da dijng chiing l&m ihutfc ch5ng co giat, thu6c an thdn.
tdy giun, Ihud'c didt co va lhu6c trir sSu (4). Ben canh do. nhi^u d3n xu^l 1,3,4-lriazoI c6n CO lac dung chd'ng vi6m. chong kh6'i u va chua bSnh lao ph6i [5]. Vdi muc dfch tim ki^m cac hgp cha't co kha nang co boat ifnh sinh hoc cao. trong cong irinh n^y, chung t6i da lien hanh t6ng hgp. nghi€n cuu ca'u tnic va thif hoat tinh sinh hoc ciia m6l so d3n xuA'l 2-amino- i5-furyl-l,3,4-thiadiazoI va l,2-diamino-5-furyI-l,3>4-triazol di tu cha't ddu la fufuroh