IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Synthesis and Characterization of New Schiffs Bases Derived from D-Erythroascorbic Acid and Pyrimidines A. A. Mukhlus , M.S. Al-Rawi , J. H. Tomma , A. H. Al-Dujaili Department of Chemistry , College of Education Ibn Al- Haitham University of Baghdad. Received in : 3 April 2011 Accepted in : 22 May 2011 Abstract The new C-5 schiff bases derived from D-erythroascorbic acid contaning pyrimidine unit were synthesized by condensation of D-erythroascorbic acid with aromatic amine (containing pyrimidine unit)in dry benzene using glacial acetic acid as a catalyst. D-erythroascorbic acid was synthesized by four steps(Schem 1), while the aromatic amine which is containing oxopyrimidine or thiopyrimidine synthesized by the reaction of chalcone urea or thiourea in acid or basic medium, respectively . The structure of synthesized compounds have been characterized by their melting points , FTIR , UV-Vis and 1HNMR spectroscopy . All the synthesized compounds have been screened for their antibacterial activities. They exhibited good antibacterial activity against Escherichia coli (G-) and Staphylococus aureus (G+) , while the compounds [V]b , [VI]b and [VII]b did not show any biological activity against this type of bacteria. Key word : Shiff bases , L-Ascorbic acid , Pyrimidines Introduction L-Ascorbic acid is one of the most important biomolecules . It acts as an antioxidant and radical scavenger widely d istributed in aerobic organisms [1]. L-Ascorbic acid derivatives have been found to possess antitumorand antiviral activities [2-4]. IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Pyrimidines have a great interest due to the wide variety of interesting biological activities observed for these compounds such as antiviral [5] , antitumor [6] , anticancer , anti- inflammetory [7] and antimicrobial [8]activities. Pyrimidine nucllosides containing C-5 alkynyl groups have been shown to possess significant antiviral and anticancer properties[9]. Herdewijn [9] synthesized many C-5 substituted pyrimidine derivatives(1) and (2) of L-ascorbic acid . These compounds exhibited antiviral and cytostatic evaluations. HN N O O O O PhCH 2O OCH 2Ph R N NO O O PhCH 2O OCH 2Ph O C R R = A lk yl or A ryl g ro up s [1] [2] Recently , Malic and et al [10] synthesized anti tumor pyrimidine derivatives of L- ascorbic acid (3) and (4) . HN N O O O O PhCH 2 O OCH 2Ph HN N O O O O OH R RO R HO [3] [ 4] R = H , F , C F 3 a nd R = H or C H 3 Ali et al [11] synthesized carbohydrate derivatives containing imine group as antibacterial . More recently , El-Sayed et al [12] and EL-Sekily [13]synthesized L-ascorbic acid derivatives containing imine group at 2- and 3- position ,compounds(5) and (6), respectivly. O O NNHPh [5] PhHNN [6] OHH OH OH O O NNHCOPhPhCOHNN OH IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Here in this work (Scheme 1) , we reported the synthesis , characterization and antibacterial activity of novel imines of L-ascorbic acid containing pyrmidine unit. O O C NH2 O X HN N S NH2 HN N O NH2 X X O OOH C O O HO HO HO OH [ I] [ II] [II I] [ IV] [V]a -d [VI]a-d [VI I]a-d [VII I]a-d [IX]a-d O O O O HO OH Me Me O O O O HO Me Me O2CAr O O HO CH CH Th io ur ea NaO H acetone d ry HCl 65% G AA NaIO4 ansoyl chloride py X CHO + C NH 2 O CH3 NaOH U rea H Cl N CH HN N S X O ON CH HN N X X = 4-NO2 , 4-Cl , 4-Me2N , 3-NO2 ; Ar= 4-CH3OC6H4- Scheme 1 ArCO2 ArCO2 Ar CO2 ArCO2 O2CAr O2CAr O2CAr O2CArAr CO2 O + O OOH C [ IV] ArCO2 O2CAr + Experimental Materials : All chemicals were supplied from Merck , GCC and Aldrich Chemicals Co. and used as received . Techniques : FTIR spectra were recorded using potassium bromide discs on a 8400s Shimadzu spectrophotometer and FTIR spectrophotometer , Shimadzo (Ir prestige-21) . 1HNMR spectra were carried out by : Bruker , model: ultra shield 300 MHz , origin : Switzerland and are reported in ppm(S), DMSO was used as a solvent with TMS as an IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 internal standard . M easurements were made at chemistry depart ment, Al-alby at university , Uncorrected melting points were determined by using Hot-Stage, Gallen Kamp melting point apparatus. UV spectra of solutions were performed on CECL 7200 Ingland Spectrophotometer using CHCl3 as a solvent . Synthesis preparation of 5,6-O-isopropylidene-L-ascorbic acid[I]: This compound was prepared from the reaction of L-ascorbic acid with Acetone in a acidic media , following Salomon methode [14]. Synthesis of 2,3-O-dianisoyl-5,6-O-isopropylidene-L-ascorbic acid [II]: To a cold solution of [I](10gm , 0.046mol) in pyridine(50 mL) , Anisoyl chloride was added (17.5mL , 0.129mol) with stirring for 2 hrs, then kept in dark place at room temperature for 24 hrs.The mixture was poured into ice-water the oil layer was extracted with (150ml) chloroform,washed with water and drived over anhydrous magnesium sulfate [15]. Filtered and the solvent evaporated, purified from chloroform:petroleum ether(1:5) to give[II] (15gm,76.5%) as a pale yellow solid ,m.p(102-104 0 C) Rf(0.80) (benzene:methanol) (5:5). Synthesis of 2,3-O-dianisoyl-L-ascorbic acid[III]: Compound[II] (10gm, 0.0236 mol) was dissolved in a mixture of (65%) acetic acid (30ml), absolute methanol(10mL) and stirred for 48 hrs at room temperature. To the resulting solution a benzene(40ml) was added and evaporated to yield[III] [16], yield (7gm, 78%) as a white crystals, m.p(130-132 0C), Rf (0.42) (benzene:methanol) (4:6). Synthesis of pentulosono-Lacton-2,3-ene - dianisoate[IV]: To a stirred solution of sodium periodate (5.6gm) in distilled water (60mL) at (0 0C), a solution of [III] (10gm, 0.026mol) in absolute ethanol (60mL) was added dropwise . After stirring 15 min, ethy lene glycol (0.5mL) was added and stirring for one hour. The mixture was extracted with ethyl acetate (3x50ml)[17]. The extracts dried over anhydrouse MgSO4 , filtered and the solvent evaporated , the residue recrystallized from benzene to y ield [IV] (4gm, 45%) as a white crystals , m.p (156-158 0 C), Rf(0.7) (benzene: methanol) (6:4). Synthesis of chalcone: 4-[3-(4`-substituted phenyl)-2-propene-1-one]-aniline [V]a-d: Equimolar quantities of 4-amino acetophenone (0.01 mol),(1.35 g) and 4- or 3- substituted benzaldehyde (0.01 mol) were dissolved in minimum amount of alcohol. Sodium IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 hydroxide solution (0.02 mol) was added slowly and the mixture became cold. Then the mixture was poured slowly into 400 mL of ice water with constant stirring and kept in refrigerator for 24 hrs [18]. The precipitate obtained was filtered , washed and recrystallized from chloroform . Synthesis of 4[6-(4`- substituted phenyl)-2-oxo-1,2, -di -hydropyrimidine-4- yl] aniline [VI]a-d : A mixture of chalcone[V]a-d (0.001 mol) and urea (0.06gm, 0.001mol ) in ethanol (20mL) and conc.hydrochloric acid (5mL) was refluxed for 6 hrs .The reaction mixture was then concentrated to half of its volume .Cooled and neutralized with ammonium hydroxide. The precipitated solid was filtered off , washed with water [19] ، dried and recrystallized from ethanol . Synthesis of 4-[6-(4`-substituted phenyl )-2-thioxo-1,2-dihydropyrimidine-4- yl) aniline [VII]a-d : A mixture of chalcone [VI]a-d (0.001mol), thiourea (0.076gm , 0.001mol) and sodium hydroxide (0.1 g) in (25 mL) of 80% (v\v) ethanol was refluxed for 6hrs. The reaction mixture was concentrated , cooled and the solid was filtered off , washed with water[19] , dried and then crystallized from ethanol. Physical data of compound[V]a-d , [VI]a-d and [VII]a-d are given in Table 1. Synthesis of Schiff bases [VIII]a-d and [IX]a-d A mixture of new amino compounds [VI]a-d (0.01 mol) , aldehyde [IV] (0.012 mol) , dry benzene (15 mL) and 2 drops of glacial acetic acid was refluxed for 6hrs . The solvent was evaporated under vaccum and the residue crystallized from chloroform. The physical data of all Schiff bases are listed in Table 2. Results and Discussion 5,6-O-isopropylidene-L-ascorbic acid[I] was prepared by the reaction of L-ascorbic acid with acetone in dry HCl (14) . The FTIR spectrum showed a broad stretching band at (3240-3074) cm-1 for(O-H) vinylic, stretching bands at (2993-2908) cm-1 for (C-H) aliphatic, acetal linkage stretching band at(1755) cm-1 due to (C=O) of Lactone ring , stretching band at(1685) cm-1 for (C=C) and stretching bands at (1141-900) cm-1 for C-O stretching . Compound [I] reacts with excess of anisoyl chloride in dry pyridine to give the corresponding ester [II]. The FTIR spectrum exhibited appearance of stretching band IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 (C=O) of the ester , and disappearance of the stretching bands for (O-H) of compound [I] , stretching bands at( 2961-2935) cm -1 for (C-H) aliphatic group , finally stretching band at (1604) cm -1 could be attributed to (C=C) aromatic. The hydrolysis of compound [II] in acid media result hydrolyzed of isopropylidene ring to yield 2,3-O-dianisoyl-L-ascorbic acid [III] which characterized by melting point and FTIR .The FTIR spectrum showed a band at (3445 ) cm-1 for (O-H) , a stretching at (3074) cm-1 for (C-H) aromatic. Glycols [III] oxidized by periodate, which is cleaves the C5- C6 bond (bearing OH groups) and formation the aldehyde compound D-erythroascorbic acid [IV].This compound is characterized by melting point , FTIR,UV-VIS, Mass and 1HNMR spectroscopy. The FTIR spectrm showed two bands at (2839-2677)cm-1 for (C-H) aldehyde stretching, a stretching band at (1715) cm -1 for (C=0) of aldehydic group , UV-Vis showed λmax at 300 nm. Mass spectrum showed M +1 =413. 1 HNMR spectrum( δ, DMSO) showed the following singal:a singlet signal at δ( 12.5) ppm that could be attributed to the aldehydic proton. Two doublet of doublets in the region δ (7.00 – 7.97) ppm due to eight aromatic protons, a singlet at δ( 3.86) ppm for proton of lactone ring at C4 . A sharp singlet at δ(3.82) ppm for the (OCH3) group. Chalcones [V]a-d are synthesized by Claisen-Schmidt condensation of 4-amino aceto phenone and 4- or 3- substituted benzaldehyde by base catalyzed followed by dehydration to yield the desire chalcons .The structural assignments of the chalcones are based on melting points and their spectral data of FTIR ,UV-Vis and 1HNMR spectroscopy. The FTIR spectra indicated the appearance of two bands in the region (3483-3273) cm -1 which could be attributed to a symmetric and symmetric stretching vibration of NH2 group , a weak band at (3119-3105) cm -1 due to stretching vibration of (CH=CH) group , two peaks at (1650) cm -1 and (1635) cm-1 are due to of (C=O) and (C=C) stretching vibration , respectively. The FTIR spectral data and UV-Vis data for the chalcones are listed in Table( 3).The 1HNMR of chalcon [V]a (δ , DMSO) fig (1), shows the following features: two pairs of doublet of doublets in the region δ (7.6-8.2) ppm which can be attributed to eight protons of two p-substituted of benzene ring showing different substituted at positions 1,4 . A doublet band at δ ( 6.6)ppm is due to two protons of (COCH=CH) [19] moiety and a doublet band at δ (8.3) ppm for proton of (=CHAr). The two protons of amine group appear as a singlet band at δ( 6.24 ) ppm. The oxopyimidine was synthesized from reaction of chalcone [V]a-d with urea in acidic medium. The structure of the oxopyrimidine [VI]a-d characteristic by FTIR spectra which are showed the disappearance of two absorption bands of new absorption bands for NH,C=O (amid) and C=N (endocyclic at ( 3433) cm -1 , (1639) cm -1 and (1610) cm -1 , respectively. FTIR characteristic bands and UV-Vis data of the synthesized compounds [VI]a- IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 d listed in Table (4) . 1 HNMR spectrum of compound [VI]b fig (2) , shows the following signals: eight aromatic protons appeared as two pairs of doublet at δ (6.7-7.5) ppm and δ (7.9- 8.0) ppm , a singlet signal at δ( 7.6) ppm could be attributed to the one proton of 1H (oxo- pyrimidine) and a singlet at δ (7.5) ppm due to the proton of CH(oxo-pyrimidine) , as singlet broad signal two protons of NH2 group appeared as δ( 5.0) ppm [19]. Thiopyrimidiens[VII]a-d were synthesized from the reaction of chalcones[V]a-d with thiourea in basic medium .The structure of the compounds [VII]a-d is characterized by FTIR, UV-VIS and 1HNMR spectroscopy . The characteristic FTIR adsorption band of thiopyrimidines showed the disappearance of two absorption bands of the (CH=CH) and (C=O) groups in the chalcones and appearance of new absorption bands for(NH, C=N and C=S) groups around (3341)cm -1 , (1620)cm -1 and (1305)cm -1 , respectively[19]. The FTIR spectral data and the UV-Vis data of these compounds are shown in Table 4 . 1 HNMR spectrum of thiopyrimidine [VII]a-d exhibited eight aromatic protons appeared as many pairs of doublet at δ (6.5-7.9)ppm,a singlet signal at δ (6.05)ppm could be attributed to the NH(Thiopyrimidine) and asinglet at δ (6.55)ppm for proton of –CH(Thiopyrimidine) , A sharp singlet at δ( 6.18)ppm due to two protons of NH2 group. The novel Schiff bases[VIII]a-d and [IX]a-d were synthesized by refluxing equemolare of D-erythroascorbic acid [VI] with amino compounds of pyrimidine[VI]a-d or [VII]a-d in dry benzene with some drops of glacial acetic the s ixteen aromatic protons , and a singlet signal at δ( 3.86)ppm that could be attributed to the proton at C4 of Lactone ring. Biological Activity The antibacterial activity of the synthesized compounds was performed according to the agar diffusion method [20]. The prepared compounds were tested against E.coli and Staph. aureus .Each compounds was dissolved in DM SO to give concentration 1ppm. The plates were then incubated at 37 0 C and examined after 24 hrs. The zones of inhibition formed were measured in millimeter and are represented by (-), (+), (+ +) and (+ + +) depending upon the diameter and clarity as in Table (6). All the compounds exhibit the highest or low biological activity while the compounds[V]b , [VI]b , and [VII]b showed no activity against both the organisms, and compound [VI]d did not show activity against only (G+) . The compounds showed good inhibition against of the two types of the bacteria, this could be related to the presence of the D-erythroascorbic acid , oxopyrimidine , thiopyrimidine and imine linkage. IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 References 1.Du ,c.; Liu , j.; Su, w.; Ren, y. and Wei, d. (2003) "The protective effect of ascorbic acid derivative on PC12 cells,Involvement of Its ROS scavenging ability" , Life Sci. , 74:771-780. 2. Tanuma, S.; Shiokawa, D.; Tanimoto,Y.; Ikekita, M. and Takeda , M.,(1993). "Benzylidene ascorbate induces apoptosis in L929 Tumor cell, Biochem, Biophys, Rrs, Commun., 194 :29- 35. 3. Velri, R.; Fodor, G.; Liu, C. and Woolverton , C. (1986) "A new class of synthetic biological response modifiers,the methylfuryl butyrolactones" , J. Biol, Res. Mod. , 5: 444- 461. 4. Woolverton,C.; Veltri, R.and Snyder , I. (1986) "Stimulation of human pmn in vitroi by asuccinimide molecular complex of methylfuryl butyrolactones", J.Biol,Res.Mod., 5 :527-538 . 5. Nasr, M. and Gineinah, M. , (2002) "Pyrido[2,3-d]pyrimidin pyrimido[5’,4’:5,6]- pyrido[2,3-d] pyrimidines as new antiviral agents: Synthesis and biological activity" Arch.pharm., 335 :289-295. 6. Baraldi, P.; Pavani, M.; Nunez, M.; Brigidi, P. ; Vitali, B.; Gambari, R. and Romagnoli R. (2002)" Antimicrobial and antitumor activity of N-heteroimine-1,2,3- diathiazoles and their transformation in triazolo-, imidazo- and pyrazolopyrimidines" .Bio.org.Med.Chem. 10: 449-456. 7. Sondhi, S.; Johar, M.; Rajvanshi,S.; Dastidar, G. ; Shukla, R.; Raghubir , R. and Lown, J. (2001)" Anticancer, anti-inflammatory and analgesic activity evaluation of heterocyclic compounds synthesized by the reaction of 4-isothiocyanato-4-methylpentan-2-one with substituted o-phenylenediamines, o-diaminopyridine and (unsubstituted o-diamino- pyrimidines". Austr. J. Chem. , 54: 69-74. 8. Chowdhury, A.; Matin , M.; and Anwar, M. (1997) "Synthesis and antimicrobial activities of fused pyrimidines: Benzothieno[2,3- d]imidazol[1,2-c] pyrimidine", Chittagong. Chittagong Univ. stud. Part(II) , 21 :79-83. 9. Herdewijn,P. (1994) "5-substituted-2-deoxy uridines as anti-HSV-1Agents : synthesis and structure-activity relationship, Antiviral Chem,Chemother". 5: 131-146. 10. Malic, S.; Sverdnzic, D.; Gazivoda , T. and Marunovic, A.(2000) "Synthesis and antitumor activities of novel pyrimidine der ivatives of 2,3-O,O-Dibenzyl-6- deoxy-L-Ascorbic acid",J. Med. Chem. 43: 4806-4811. IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 11. Ali, U .; AL-Rawi , A. and AL-Rawi , M. (1998) "Synthesis of some new Schiff bases derived from glucosamine of possible anti microbial activity" J.Drrasat,Natural and Engineering sciences,25(1):95. 12. El- Sayed , H. ; Atta , K. ; Aboul-Ela , S. and Beldi , R. (2007)" Microwave Assistant synthesis of Mono- and Bis- Phenylhydrazones of L-Threo-and-D-Erythro-2,3- Hexodiulosono-1,4-Lactones for The Synthesis of an Array of Heterocyclic Compounds", Jordan J. of Chemistry , 2(1): 117-124. 13. EL-Sekily , A. (2008) "Hydrogenation products from dehydro-D-Erythro- and L-Threo- Ascorbic acids mono- and bishydrazones".,The Arabian Jou.for science and engineering,33(1A), 7-13. 14. Salomon, L.(1963) Experientia ,19(12) :619. 15. Jwad, R. (2006) "Synthesis of new oxazepine derivatives starting from L-ascorbic acid", Thesis , Education College Ibn Al-Haitham, University of Baghdad. 16. Loudon, G. (2002) "Organic Chemistry",4th Ed.,Oxford University press,Inc.,New York, ,855-856,869 and 873. 17. Al-Ogiady, R. (2010)"Synthesis of new Malonate and Barbiturate derivatives of D- Erythroascorbic acid and their Metal complexes",Ph.D.Thesis, Education College Ibn Al- Haitham ,University of Baghdad. 18. Kalirajan , R.; Sivakumar, S.; Gowramma , S. ; Jubic, B. and Saresh , B. (2009) International J. Chem.Tech Res.,1(1): 27-34. 19. Fathalla , O . ; Awad, S. and Mohamed, M. (2005) "Synthesis of new 2-Thiouracil-5- Sulphonamide derivatives with Antybacterial and Anti Fungl activity",Arch pharm Res.,28(11):1205-1212. 20. Allawy, H. (2000) "Synthesis of some new bis-1,4-substituted butane derivatives containing 1,3,4-Oxadiazole or 1,2,4-Trizole unit", M.Sc Thesis, Education College Ibn Al- Haitham,Baghdad University. IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Table(1):The physical properties compounds[V]a-d,[VI]a-d and [VII]a-d. Color Yield % M.P C0 Molecular Formula Structural Form ula Nomenca lture Comp. No. Orange 90 210 C15H12N2O3 CH NHC O CHO2N 4[3-(4`-nitropheny l)-2- propene-1-one] aniline [V]a Yellow 75 164 C15H12 NOCl CH NHC O CHCl 4[3-(4`-chloropheny l)-2- propene-1-one] aniline [V]b Red 60 140 C17H18N2O CH NC O CHMe2N 4[3-(4`-N,N-dimethy lpheny l)- 2-propene-1-one] aniline [V]c Dark Orange 80 204 C15H12N2O3 CH NC O CH O2N 4[3-(3`-nitropheny l)-2- propene-1-one] aniline [V]d Orange 70 214- 218 C16H12N4O3 HN N NHO2N O 4[6-(4`-nitropheny l)-2-oxo-1, 2-dihy dro- py rimidine-4- y l]aniline [VI]a Yellow 55 208 C16H12N3OC l HN N O NCl 4[6-(4`-chloropheny l)-2-oxo- 1,2-dihy dro- py rimidine-4- y l]aniline [VI]b Red 50 212 C18H18N4O HN N NMe2 N O 4[6-(4`-N,N-dimethy l pheny l)- 2-oxo-1, 2-Dihydro py rimidine -4-yl] aniline [VI]c Orange 70 197 C16H12N4O3 HN N O O2N 4[6-(3`-nitropheny l)-2-oxo-1, 2-Dihydropy rimidine -4-yl] aniline [VI]d Pale brown 60 276 C16H12N4O2S HN N O2N S 4[6-(4`-nitropheny l)-2-thioxo- 1, 2-dihy dro-py rimidine-4- y l]aniline [VII]a Yellow 65 200 C16H12N3SCl HN N Cl S 4[6-(4`-chloropheny l)-2- thioxo-1, 2-Dihy dro py rimidine -4-yl] aniline [VII] b Yellow 50 162- 164 C18H18N4S HN N NMe 2N S 4[6-(4`-N,N-dimethy l pheny l)- 2-thioxo-1, 2-Di hy dro py rimidine -4-y l] aniline [VII]c Brown 50 150 C16H12N4O2S HN N S O2N 4[6-(3`-nitropheny l)-2-thioxo- 1, 2-Dihydro py rimidine -4-yl] aniline [VII] d IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Table(2):The physical properties compounds [VIII]a-d and [IX]a-d. Color Yield % M.P 0C Molecular formula Rf Structural formula Comp. No. Yello w 50 185- 187 C37H26O11N4 0.31 O O ArCO 2 O 2CAr N CH HN N O O 2N [VIII]a Brow n 55 190 C37H26O9N3Cl 0.35 O O ArCO 2 O 2CAr N CH HN N O Cl [VIII]b Brow n 50 >300 C39H32O9N4 0.16 O O ArCO 2 O 2CAr N CH HN N O Me 2 N [VIII]c Oran g 60 124- 126 C37H26O11N4 0.36 O O ArCO 2 O 2 CAr N CH HN N O 2N O [VIII]d Brow n 55 >300 C37H26O10N4S 0.37 O O ArCO 2 O 2CAr N CH HN N S O 2N [IX]a Brow n 50 >300 C37H26O8N3Cl S 0.47 O O ArCO 2 O 2CAr N CH HN N Cl S [IX]b Red 60 170 C39H32O8N4S 0.28 O O ArCO 2 O2 CAr N CH HN N S Me 2N [IX]c Yello w 65 144 C37H26O10N4S 0.21 O O ArCO 2 O 2 CAr N CH HN N O 2N S [IX]d IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Table(3) :Charcterrisitic FTIR absorption band and UV data ( λ max) of compound [V] Table(4):Characteristic FTIR absorption bands and UV data (λmax) of compounds [VI]a- d and[VII]a-d Characteristic bands FTIR spectra (cm-1) UV data Comp. No. others νC=S νC=C aromatic νC=N endocyclic νC=O amide νC-H aromat ic νNH2 asy . , sy. and νNH λmax (nm)in CHCl 3 4-NO2 :1508 ,1343 1589 1610 1640 3100 3484,3387,3256 307 [VI]a 4-Cl:1080 1605 1630 1645 3053 3460,3342,3217 318.5 [VI]b 4-N(Me)2:1168 1567 1610 1643 3036 3425,3390,3213 339 [VI]c 3-NO2 :1346 1609 1636 1645 3094 3472,3418,3341 279 [V I]d 4- NO2:1512,1338 1312 1597 1628 3067 3460 , 3333,3221 354.5 [VII]a 4-Cl:1087 1288 1597 1620 3050 3456,3341,3221 319.5 [VII]b 4-N(Me)2:1168 1304 1597 1620 3053 3476,3433,3329 408.5 [VII]c 3-NO2:1346 1308 1589 1628 3086 3410,3383,3360 266 [VII]d Characteristic bands FTIR spectra (cm-1) UV data Comp. No. others νCH=CH νC=O νNH 2 asy . , sy. λmax (nm) in CHCl3 4-NO2 :1504,1342 1635 1650 3483 , 3387 306 [V]a 4-Cl:1089 1632 1670 3385-3273 341.5 [V]b 4-N(Me)2 :1165 1630 1662 3480-3236 342.5 [V]c 3-NO2:1346 1632 1651 3426-3333 284.5 [V]d IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Table(5):Characteristic FTIR absorption bands and UV data (λmax) of compounds [VII]a-d and [IX]a-d Table(6): Antibacterial activity of the prepared compounds Key to symbols: Highly active = + + +(mor than)15 mm. Moderately active = + +(11-15) mm. and Slightly active = + (5-10) . Character istic bands FTIR spec tra (cm-1) UVdata Comp. No. νC- O νC=S νC= C aro m. νC=N endocy c. νC=N exocyc . νC=O am id νC=O ester VC=O Lacton νC-H aliph. ν C-H arom. νNH λmax(nm) in CHCl3 1263 1602 1615 1637 1653 1738 1760 2982-2847 3052 3390 258 [VIII]a 1261 1590 1605 1630 1659 1735 1767 2962-2839 3059 3417 234 [VIII]b 1257 1585 1605 1640 1650 1715 1766 2978-2839 3060 3402 258.5 [VIII]c 1237 1580 1605 1632 1642 1724 1770 2984-2878 3059 3337 268.9 [VIII]d 1257 1310 1601 1610 1630 1645 1720 1766 2962-2843 3078 3348 252.6 [IX]a 1261 1300 1585 1605 1627 1650 1730 1766 2981-2843 3050 3406 261 [IX] b 1258 1305 1580 1600 1630 1642 1715 1766 2908-2949 3078 3383 258.5 [IX] c 1263 1304 1580 1605 1627 1645 1720 1769 2982-2843 3059 3368 252.4 [IX]d Staph.aureus (G+) E.Coli (G-) Comp. No. Staph.aurus (G+) E.Coli (G-) Comp. No. + + + + + [VIII]a + + + + + [V]a + + + + + + [VIII]b - - [V]b + + + + + + [VIII]c + + + + [V]c + + + + + + [VIII]d + + + + ++ [V]d + + + [IX]a + + + + [VI]a + + + + + + [IX] b - - [VI]b + + + + + + [IX] c + + + + + + [VI]c + + + + + + [IX]d - + [V I]d + + + + [IV] + + + + + [VII]a - - [VII]b + + + [VII]c + + + + + + [VII]d IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Fig. (1): 1HNMR- spectrum of compound[V]a Fig . (2): 1 HNMR-spectrum of compound[VI]b IBN AL- HAITHAM J. FOR PURE & APPL. SCI. VOL.24 (2) 2011 Fig .(3): FTIR-spectrum of compound[VIII]d Fig .(4) : 1HNMR-spectrum of compound[VIII]a 2011) 2( 24المجلد مجلة ابن الھیثم للعلوم الصرفة والتطبیقیة ارثرو اسكوربیك - Dتحضیر و تشخیص مشتقات جدیدة من قواعد شف لحامض و البیرمیدین عمار ھاني الدجیلي، جمبد ھرمز توما ، منى سمیر الراوي ، عبد الجبار عبد القادر مخلص جامعة بغداد ، ابن الھیثم –كلیة التربیة ، سم الكیمیاء ق 2011نیسان 3: في استلم البحث 2011آیار 22: قبل البحث في الخالصة ارثرو اسكوربیك مع مركبات البیریمیدین التي - Dحضرت المركبات الجدیدة لقواعد شف المشتقة من حامض في البنزین ) المحتویة على وحدة البیرمیدین(ارثرواسكوربیك مع االمینات االروماتیة - Dحضرت من تكاثف حامض ت - Dحضر الحامض . الجاف وباستعمال قطرات من حامض الخلیك الثلجي محفزا ارثرواسكوربیك باربع خطوا الیوریا او الثایوریا في وسط بینما حضر االمین االروماتي من تفاعل الجالكونات مع ) 1(متتالیة كما في المخطط رقم .حامضي او قاعدي وعلى التوالي وطیف ,FTIR UV-Visشخصت جمیع المركبات المحضرة بقیاس درجات انصھارھا وبوساطة طیف 1HNMR . ة محضرة ضد نوعین من البكتریا واظھرت النتائج فعالیة بایولوجی درست الفعالیة البایولوجیة للمركبات ال , b[V]ات بینما لم تظھر المركب Staphylococcus (G+) ,Echerichia coli (G-).یدة ضد البكتریا بنوعیھا ج [VI]b , [VII]b نوع من البكتریا .اي فعالیة بایولوجیة ضد ھذا ال . بیرمیدین ,حامض االسكوربیك , قواعد شف : الكلمات المفتاحیة