... 232 ,5- 253 ,0- 0, 450 65, 22 0 ,52 0 58 0 ,53 0 59 0,180 42 0,230 54 254 ,5 248 ,52 50,0 Két tinh, màu dơ sâm 298 ,5- Két tinh 240- 30 63,8 270 ,5 510 nhat 0, 350 268,0- 257 ,5- Br 9 ,5: 0 ,5 234 ,5 Két tinh màu vàng... hydrazon cüa 5- (5 -bromovanilyliden)- thiazolidin- 2,4- dion (Chât VI) * 2,4- dinitro phenyl hydrazon cüa 5- (5 -bromovanilyliden)- thiazolidin2 ,4 -dion (Chât VII) * Isonicotinoyl hydrazon cüa 5- (5 -bromovanilyliden)- thiazolidin- 2, 4dion. .. chï tham dơ tâc dung sinh hoc cüa chât thiazolidin- 2,4- dion; 5- (5 bromovanilyliden)- thiazolidin- 2,4- dion; 2,4- dinitrophenylhydrazon cüa 5- (5 bromovanilyliden)- thiazolidin- 2,4- dion vơi chüng vi khn
..... ........ 5.. m B Ô Y TE T R l / Ô N G BAI H À NÔI. .■ H O■ C Dl/OC ■ ■ ______________* * * __________________ NGUYEN VÂN PHUC TÔNG HOP VÀ THÂM DÔ TAC DUNG SINH HOC CÜA 5-(5’-BROMOVANILYLIDEN)-THIAZOLIDIN-2,4-DION VÀ DÂN CHAT. KHO LUÂN TÔT NGHIÊP DUdC SÎ KHO 1998-2003. Giâo viên hwâng dan: TS Nai thuc hiên: . Pham Thj Minh Thüy. Bô mon Hoâ hCfu ca. Thdi gian thuc hiên: 02/03/2003-20/05/2003. HÀ NÔI 5 - 2003. m t — M @ r m '' LCJI CAM ON (San 3 fh am f /à n i oiêe tielt euo où U hâit tru ’&tig., d u o ! su ’ (filift ïtiï n h iê t fin/t e u a e a e thaï/ et) t/iât) eut îtü h f)àn th à n h U hoâ lu tin 9 f ÇJmty li d p tut ih a m d è tac. dung, iin h ht)e eu a 5-(5 hv(m it)tuinilifliden) thiaïL()Udhi-2,4-dUm tut d a n ch û t . (Z)âi long hiet on $au sae em æin ch an thành eàm tin: ÇJien sJ ^Phani Ç jlii Jllin h ÇJhug QZgtioi tru'e tièft huong dan tan finit eho em thue h/en Uhoa lugn u àg. 2.0000 ABS Base line Erase Uieu Re-scale Zoom Use the graphies cursor■ track■ slope____ 400.00 2.0 MM "35E33- 360.00 : 200.00 -> Label More 400.00 400.00 357.000 255.000 Pho tû ngoai cüa chât I Mau 02 - Phuc/HCo Gain 84 SBU Page Basel ine____ OFF 0.0003 ABS___________ 23 Apr 2003 2.0 3___________ 550.00 __________ MM DISPLAŸ DATA 2.0000 1.6000. 1 .2000. fv _ . 0.8000- / \ 0.4000- 0.0000Ji---200.00 ABS________ 300.00 0.0000 -> 2.0000 Baseline Erase Uiew Re-scale Zoom Use the graphies cursor. track. slope_____ 400.00 500.00 200.00 MM Labe1 Pho tû ngoai cüa chât II More -> 550.00 0 .01905 0 .04214 0 .45611 0 .46020 0.49857 ABS ABS ABS ABS ABS - 0.0045 _______ a bs NM NM NM NM NM 726 .000 543 .000 385 .000 220 .000 208.000 Mau 07 - Phuc/HCo Gain 120 Basel ine_____ OFF 23 Apr 2003 SBU Page 6 0 0 .0 0 2.0 3__________ ___________ MM DISPLAŸ DATA 0.8000 0.6000- •N-NH-C6H3(N 02)2 c h , /" 0.4000' 0.2000 1 0.0000 i---200.00 " 0.0000 -> 0.8000 ABS________ Re-scale 2oom Baseline Erase Uieu Use the graphies cursor, track. slope____ ABS ABS ABS 0.83195 0.38956 0.67475 600.00 400.00 NM NM NM NM ~5TEB33~ 800.00 : 200.00 Label More 800.00 354.000 253.000 217.000 Pho tu’ ngoai cüa chât VII 0.0004 ABS _____ Mau 08 - Phuc/HCo Gain 93 SBU Base 1ine____ OFF Page 23 Apr 2003 2.0 3____________ 500.00 __________ NM DISPLAY DATA 2 .0000 1.6000. 1 . 2000 _ 0.80000.4000- 0.0000 200.00 — i------------------------------ 1----- 1 400.00 300.00 0.0000 -> 2.0000 ABS Uieu Re-scale 2oom Baseline Erase Use the graphies cursor, track, slope MM ~3!B5SIBr~ : 200.00 -> Label More Pho tir ngoai cüa chât VIII 2 500.00 500.00 1 .66635 0 .67265 1 .01964 ABS ABS ABS 0.0001 ABS___________ NM NM NM 357.000 253 .000 217.000 Mau 03 - Phuc/HCo Gain 84 Basel ine____ OFF SBU Page 23 Apr 2003 2.0 3___________ 550.00 ___________ MM DISPLAY DATA 3.0000 2 .0000 _ / 1 . 0000 - 0 . 0000 200.00 0.0000 -> 3.0000 ABS________ Baseline Erase Uieu Re-scale Zoom Use the graphies cursor. track. slope____ ABS ABS ABS 0.90756 0.38986 0.59026 NM NM NM 500.00 400.00 300.00 200.00 NM M Label -> 550.00 More 357.000 252.000 218.000 Pho tir ngoai cüa chât III - 0 .0 0 0 2 ABS___________ Mau 04 - Phuc/HCo Gain 84 SBU Basel ine____ OFF Page 23 Apr 2003 2.0 3____________ 550.00 __________ MM DISPLAY DATA 2 .0000' 1.6000. 1 . 2000 . 0.8000- / 0.4000- / : * 0.0000 200.00 ABS 300.00 r 0.0000 -> 2.0000 Baseline Erase Uieu Re-scale Zoom Use the graphies cursor, track. s i o p e _ NM ~m s s r ~ Label Pho tir ngoai cüa chât IV 3 500.00 400.00 200.00 More -> 550.00 0 ,70290 0 .29398 0.45044 ABS ABS ABS 0.0006 _flBS___________ NM NM NM 358.000 251.000 217 .000 Mau 05 - Phuc/HCo Gain 84 Basel ine____ OFF 23 Apr 2003 SBU Page 2.0 3___________ 550.00 NM DISPLAŸ DATA 1.2000 0.8000- 0.4000- 0.0000 i---- T 200.00 400.00 300.00 NM 0.0000 -> 1.5000 ABS________ Baseline Erase Uieu Re-scale Zoom Use the graphies cursor. track, slope____ 0 .64234 0.26782 0.39844 ABS ABS ABS 0.0002 ABS___________ ' 5 0 0 . 0 0 : 200.00 -> Label More 550.00 357 .000 250 .000 216.000 NM NM NM Pho tur ngoai cüa chât V Mau 06 - Phuc/HCo Gain 84 Basel ine____ OFF 23 Apr 2003 SBU Page 2.0 3 ___ 550.00 __________ MM DISPLAV DATA 1 .2000' 0.8000- 0.4000- 0 . 0000 - 200.00 ABS 0.0000 -> 500.00 400.00 300.00 1.4000 Base line Erase Uieu Re-scale Zoom Use the graphies cursor. track. slope____ NM Label Phô tir ngoai cüa chât VI 4 200.00 -> More 550.00 PEHKIN ELMER 35.73-1 XT 00 m UD 11.75- ..t 4000 3500 3000 2500 03/04/25 13:35 Phong TNTT-DH Duoc X: 1 scan, 4.0cm-i, fiat, smooth Samp.01-Phuc/Hco 2000 thiazolidin-2,4-dion p h ^ h ^ n g ngoai cûa 1500 j PERKIN ELMER 2 7 .5 5 - ZT esI a . ‘.O rH i3 2 I LlO LT> rO LTÏ CS> UD UD IN- m en GD OJ e s CD CO CVI l.\J t) iS CT' r_ -0 .4 9 4000 3500 ...h3000 2500 2000 1500 5-(5 ’-bromovanilyliden) thiazolidin-2,4dion 03/04/25 13:39 Phong TNTT-DH Duoc Y: 1 scan, 4.0cm-l, fiat, smooth Samp.02-Phuc/Hco Pho hông ngoai cüa chât II 1000 cm-1 500 PERKIN ELMER 33.14-1 XT ■^T I UD CT. I Clo r o CSJ 1J 1 en CD CD CD CS CO OJ s 7I §r-» LO co I LO 1 . 64—y 4000 3500 3000 2500 2000 en fq 1500 1000 ♦> Oxim cüa 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion. 03/04/25 13:57 Phong TNTT-DH Duoc Y: 1 scan, 4.0cm-l, fia t, smooth Samp.03-Phuc/Hco PhOh°Dg ngoai cüa chât III 500 cm- PERKIN ELMER 26. 46-1 XI 00 i-D I :en» u'jro ü m'i œ i3D iS ï- m CD I nt UD LT> œ m en 7.124000 3500 3000 2500 2000 1500 1000 ❖ Semicarbazon cûa 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion. 03/04/25 13:49 Phong TNTT-DH Duoc X: 1 scan, 4.0cm-l, fia t, smooth Samp.04-Phuc/Hco Pho hông ngoai CÜa chât IV PERKIN ELMER 27.90-] ZT ■ ^r UD I en CD 00 LO UD I CD ! ‘D i u'> CD r eo s en r- OJ s 0.964000 W r- f3 s —t — 3500 3000 2500 2000 ❖ Thiosemicarbazon cûa 03/04/25 14:02 Phong TNTT-DH Duoc Z: 1 scan, 4.0cm-l, fiat, smooth Samp.05-Phuc/Hco 1500 1000 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion. Pho hông ngoai CÜa chât V 500 cm-1 PERKIN ELMER 27.90-1 ZI m GD en •jo s cô I «-1 OJ en TJ- co LTj UD •Xi LTÎ T —cr ■* I fr;fi SKÎ I I^ CO CO 'T CD CD CD CO OJ Si f*4- § £ \à 0.964000 3500 3000 2500 2000 1500 1000 ❖ Phenyl hydrazon cüa 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion. 03/04/25 14:07 Phons TNTT-DH Duoc X: 1 scan, 4.0cm-l, fiat, smooth Samp.06-Phuc/Hco Pho hông ngoai cüa chât VI 500 cr PERKIN ELMER 2 7 .9 0 ZT NH N ~ N H -C 6H3(N 0 2) c h LT* in rH m INÇVJ œ i i m ro co CS)CS) 00 ^r R - >JD 0.964000 - 1— 3500 ■..i— 3000 2500 >000 1500 1000 ❖ 2,4- dinitro phenyl hydrazon cûa 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion 03/04/25 14:13 Phong TNTT-DH Duoc Y: 1 scan, 4.0cm-l, fiat, smooth Samp.07-Phuc/Hco PhÔ hông ngoai CÜa chât VII 500 cm*1 , PERKIN ELMER 27.40XT 3 en I cô^ ® CS.» t2 LO f fi >.JD II en en uu>r> co c -~es ÜOLD mm CD r -a TT en en r- CD ro ,r: I m m 0.454000 -- !--- 3500 3000 2500 ♦> Isonicotinoyl 03/04/25 14:21 Phong TNTT-DH Duoc Z: 1 scan, 4.0cm-l, fiat, smooth Samp.08-Phuc/Hco 2000 hydrazon ra IÛ en TT 1500 cüa 1000 500 5-(5’-bromovanilyliden)-thiazolidin-2,4-dion Pho hông ngoai CUa chât VIII errr [...]... S\^N-NH-C6H3(N02)2 VII N H o S^/^N-NH-CH^ 'N VIII Xổ 232 ,5- 253 ,0- 0, 450 65, 22 0 ,52 0 58 0 ,53 0 59 0,180 42 0,230 54 254 ,5 248 ,52 50,0 Kột tinh, mu dụ sõm 298 ,5- Kột tinh 240- 30 63,8 270 ,5 510 nhat 0, 350 268,0- 257 ,5- Br 9 ,5: 0 ,5 234 ,5 Kột tinh mu vng nhat mu vng suõt % 166 ,5 420 449 Hiờu 0 ,51 0 50 0,770 56 0 ,58 0 35 258 ,5 302,0 243 ,5 ... phenylhydrazon cỹa 5- (5- bromovaniIyIiden )thiazolidin- 2,4- dion (chõt VI) *Nguyờn tõc: -NH + h 2n - n h - c 6 h 5 H H20 n - n h - c 6h 5 ,OC H, CTPT:C17H 140 3N3SBr M=420,0 *Tiộn hnh: Trong binh cõu dõy tron dung tfch 150 ml cho vo dụ 1,65g (0,005mol) 5- (5- bromovanilyliden)- thiazolidin- 2,4- dion v 0,5ml phenyl hydrazon (0,005mol), roi thờm 25ml alcol ethylic tuyờt dụi, ho tan cho tan hột roi thờm vi giot (3 -5 giot)... HOP Dua vo tfnh chõt v khõ nng phõn ỷng cỹa dõn chõt thiazolidin- 2, 4dion v vanilin Chỹng tụi dụng vong giỷa thioure v acid monocloroacetic thu duoc thiazolidin- 2,4- dion Sau dụ cho thiazolidin- 2, 4dion ngung tu vụi 5 bromovanilin thu duoc 5- (5- bromovanilyliden)- thiazolidin- 2,4- dion Sõn phõm cụn nhom carbonyl vi tri sụ 4 (trong khung thiazolidin- 2,4- dion) cụ thộ tham gia phõn ỷng ngung tu vụi cõc hop... semicarbazon cỹa 5- (5- bromovanilyliden )thiazolidin - 2,4- dion (chõt IV) *Nguyờn tõc: - NH ^ S - NH o n -n h -c -n h 2 CTPT:CHn0 4N4SBr M=387,0 *Tiộn hnh: Cõnl, 65( g) (0,005mol) 5- (5- bromovanilyliden)- 2,4- dion v 0 ,56 (g) (0,0 05 mol) semicarbazid, cho vo bợnh cu dõy trụn dung tfch 150 ml roi thờm vo 25ml alcol ethylic tuyờt dụi, ho tan nụng hụn hop trờn sau dụ thờm (3 -5 giot) acid acetic dc Lp sinh hn hụi... H20 /5: l hoc hụn hỗfp dung mụi Aceton:Ethanol/8:3 Sõn phõm sau khi tinh chộ dem sõy 50 -60C Thu duofc 9 ,58 g sõn phõm kờt tinh hinh kim, mu vng chanh * Ket quõ: Hiờu suõt 58 % Nhiờt dụ nụng chõy 232 ,5- 234,5C Rj=0 ,52 0 (CH3C1: H20 / 9:1) 2.3.4 Tong hofp dõn chõt oxim cỹa 5- (5- bromovanilyliden)- thiazolidin2 ,4 -dion (chõt III) *Nguyờn tac: CIPT :Cj jH80 4N2SBr M=3 45, 0 *Tiộn hnh: Cõn 1,65g (0,005mol) 5- (5, -bromovanilyliden)- thiazolidin- 2,4- dion. .. isonicotinoylhydrazon cỹa 5- (5- bromovanilyliden )-thiazo!idin -2,4- dion (chõt VIII) *Nguyờn tac: CTPT :C 17H120 4N4SBr M=449,0 *Tien hnh: Trong binh cõu dung tich 150 ml cho vo dụ 1,65g (0,005mol) 5- ( 5bromovanilyliden)- thiazolidin- 2,4- dion v 0,69g (0,005mol) rimifon (isonicotinoyl hydrazon) Sau dụ thờm 25ml alcol ethylic tuyờt dụi, ho tan 28 nụng hụn hỗfp trờn roi thờm vi giot (3 -5 giot) acid clohydric dc Lp sinh hn... CHCl3:MeOH/9:l, vột sac k thu duoc sach, gon vụi Rp0, 35 2.3.3 Tong hop 5- (5- bromovanilyliden)- thiazolidin- 2,4- dion (chõt II) *Nguyờn tõc: CTPT:CnH80 4NSBr M=330,0 *Tiộn hnh: Trong binh cu dung tfch 150 ml ho tan 5, 85g (0,05mol) thiazolidin2 ,4 -dion v 8,4g natriacetat (0,1 mol) trong 60ml acid acetic dc, sau cho tiộp 11 ,55 g (0,05mol) 5- bromovanilin 22 Lp sinh hn hụi liru, mõy khuõy, roi dun soi hụn hop phõn ung trong... C6 H3 (N 0 2 ) 2 CTPT:C17H 120 7N5SBr M =51 0,0 *Tiộn hnh: Cõn 1,65g (0,005mol) 5- (5- bromovanilyliden)- thiazolidin- 2,4- dion v 0,99g (0,005mol) 2,4- dinitrophenylhydrazon, cho vo bùnh cu dõy trụn dung tfch 150 ml rụi thờm 25ml alcol ethylic tuyờt dụi Ho tan nụng hụn hop trờn rụi thờm vi giot (3 -5 giot) acid clohydric dõc Lp sinh hn hụi luu v dun cõch thu trong thụi gian 2 ,5 giụ Sau dụ do hụn hop phõn rùng... oh Br CTPTặ^HnO.N^Br M=403,0 *Tiộn hnh: Trong binh cõu dung tfch 150 ml, cho vo 1,65g (0,005mol) 5- (5- bromo vanilyliden) -thiazolidin- 2,4- dion v 0,46g (0,005mol) thiosemicarbazid Ho tan hụn hỗfp trờn trong 25ml alcol nụng roi thờm (3 -5 giot) acid acetic, lp sinh hn hụi luu v dun cõch thu trong 2 ,5 giụ Hụn hop sau phõn ỷng duoc do ra 25 cục, dộ nguụi, lm lanh, cho tỹa hon ton thi dem loc qua phờu Buchner... metylen(-CH2-) trong nhõn thiazolidin- 2,4- dion +Tham gia phõn ỷng thộ :Nguyờn tỷ hydro trong nhụm metylen cụ thộ bi thộ bụi cõc nhụm thộ khõc nhau Bhagara [12] cho thiazolidin- 2,4- dion phõn lợng vụi PhN2+Cl' v thu duoc sõn phõm thộ azo -N R 'O +phN>c l ^ 5 c ợ D.J Taylor [26] cho thiazolidin- 2,4- dion phõn ỷng vụi benzylclorid trong mụi truụng amoniac long tao thnh 5- benzyl thiazolidin- 2,4- dion > ^ N H 1 I