ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Synthesis and Antibactrial Study of New 2-Amino-5-Aryl- 1,3-Thiazole-4-Carboxylic Acid Derivatives Zina K. Al- Dulaimy Aoras A. Kadhim Dept. of Medical Chemistry / College of Medicine / University of Wassit Abduljabbar Kh. Attia Mohammed Z. Thani Dept. of Chemistry/College of Science / Al-Mustansiriya University Received in : 4 October 2012 , Accepted in : 30 December 2012 Abstract 2-Amino-5-aryl- 1,3-thiazole-4-carboxylic acid (A1-A3) were synthesized from the reaction of various aromatic aldehyde with dichloro acetic acid and thiourea. The synthesis of 2-[[(S- aminosulfinim-idoyl)(aryl)methyl](benzoyl)amino]-5-aryl-1,3-thiazole-4-carboxylic acid (A22-A30) was perfomed starting from (A1-A3) by two steps using Schiff's base (A4-A12) prepared from the reactant compounds (A1-A3) with different aromatic aldehyde. Finally two types of imide derivatives were obtained from reactant compounds (A1-A3) with malic anhydride (A31-A33) and phthalic anhydride (A34-A36) in the presence of glacial acetic acid. All proposed structures were supported by FT-IR and UV-Visible spectroscopic data. Key word: 1,3-thiazole-4-carboxylic acid, imide derivatives, Schiff's base. 188 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Introduction Thiazole derivatives have attracted a great deal of interest owing to their antibacterial, antifungal, anti-inflammatory, CNS depressant, antitubercular, anti-tumor, anthelmintic, sedative hypnotic and anti-retroviral properties. In addition to being used in the pharmaceutical industry, thiazoles also found wide application in the dye and photographic industries.[1-5] There has been considerable attention to the chemistry of Schiff's bases because of their wide range of applications in many fields including biological, organic, inorganic and analytical chemistry. They are used as pigments, dyes, and catalysts, intermediates in organic and inorganic synthesis and polymer stabilizers.1-4 Schiff bases containing heterocyclic rings are known to show cytotoxic, anticonvulsant, antimicrobial, anticancer, antifungal, antimalarial, antiviral, antidepressant and enzyme inhibitor activities.5-11 Furthermore, some Schiff bases are used in ion sensors and electrochemical sensors to empower detection with enhanced selectivity and sensitivity.[6-8] Moreover, thioureas and their derivatives show strong antibacterial activity and are versatile reagents in organic synthesis. [9] The aim of this work was synthesize some Substituted of 1,3-thiazoles that can be used for farther study as therapeutic agents. Experimental All melting points were recorded on an electrothermal Gallen Kamp melting point apparatus and are uncorrected. The FTIR-spectra was recorded on Shimad ZN- FTIR 8400S Spectrometer in form of KBr disc. UV spectrophotometer using absolute ethanol as solvent. Characterization of the products is given in Table (1). Synthesis of compounds 2-Amino-5-aryl- 1,3-thiazole-4-carboxylic acid (A1-A3) [10] To a mixture of appropriate aldehydes (0.01 mole) and sodium hydroxide (0.01 mole) in absolute ethanol (15 ml) dichloroacetic acied (0.01 mole) and thiourea (0.01 mole) was added, the mixture was refluxed for (4hrs.) and cooled to room temperature. The precipitate was filtered and recrystallized from ethanol. Synthesis of compounds 5-Aryl-2-{[(1E)-arylmethylene]amino}-1,3-thiazole-4-carboxylic acid (A4-A12)[11] General procedure To stirring solution of compounds (A1-A3) (0.01 mole) in absolute ethanol (15 ml) appropriate aldehydes (0.01 mole) was added, the mixture was refluxed for (6hrs.) and cooled to room temperature. The precipitate was filtered and recrystallized from ethanol and water (3:7). Synthesis of compounds 2-{benzoyl[chloro(aryl)methyl]amino}-5-aryl-1,3-thiazole-4- carboxylic acid (A13-A21)[12] To a stirring solution of a compounds (A4-A12) (0.005 mole) in dry benzene (10 ml), benzoyl chloride (0.005 mole) in dry benzene (10 ml) was added dropwise, the mixture was refluxed for (1hr.), after cooling, the precipitate was filtered and recrystallized from benzene. Synthesis of compounds2-[[(S-aminosulfinimidoyl)(aryl)methyl] (benz-oyl) amino]-5- aryl-1,3-thiazole-4-carboxylic acid (A22-A30)[13] To stirring solution of compounds (A13-A21) (0.01 mol) in absolute ethanol (20 ml), thiourea (0.01 mol) was added, the mixture was refluxed for (5hrs.) and cooled to room temperature. The solid product was filtered and recrystallized from ethanol. Synthesis of compounds2-(substituted-1H-pyrrol-1-yl)-5-aryl-1,3-thiazole-4-carboxylic acid (A31-A36)[14] 189 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 To solution of compounds (A1-A3) (0.01 mol) in acetic acid (15 ml), ) appropriate anhydride (0.01 mol) was added, the mixture was refluxed for (8hrs.) and cooled to room temperature. The precipitate was filtered and recrystallized from aqueous ethanol (7:3) . Antibacterial Activity Tests The antibacterial activity tests were performed according to agar diffusion method [14] using Cefotaxime, Penicillin and Ceftazidime as the reference compounds. The sterile cotton swabs were separately dipped into each of the adjusted organism cultures and excess inoculum was removed by pressing and rotating the swab firmly several times against the wall of the tube above the level of the liquid. The swab was streaked all over the surface of the nutrient agar in three dimensions at an angle of 60° to obtain an even distribution of the inoculum. The plates were then left to dry at room temperature for few minutes. A sterile cork porer (8 mm in diameter) is used to make wells in the solid nutrient agar plates, so that the distance between the edges of each two wells is not less than 24 mm. Fill each well with 75 μL of the test compound and another well with same volume of DMF as a vehicle control. Allow a period of free diffusion for 2 h, then incubate at 37 °C for 18–24 h. 190 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 S N NH2 Ar COOH Ar-CHO+ Cl2CHCOOH+ H2NCSNH2 Ar`-CHO S N Ar`-CH=N Ar COOH PhCOCl S N N Ar COOH CHAr` Cl C Ph O S N N Ar COOH CHAr` S C Ph O C NH2 NH H2N-CS-NH2 S N N Ar O O COOH S N N Ar O O COOH A1-A3 A4-A12 A34-A36 A31-A33 A13-A21 A22-A30 Ar = o-NO2C6H4-, p-(CH3)2NC6H4-, p-BrC6H4- Ar` = o-NO2C6H4-, p-(CH3)2NC6H4-, p-BrC6H4- Result and Discussion The compounds (A1-A3) were prepared by the reaction of dichloro acetic acid with thiourea that give a good yield. The IR spectra showed the (C=O) stretching band at (1697 cm-1) and (C=N) in (1646 cm-1). The reaction between compounds (A1-A3) and some aldehyde afforded the Schiff bases (A4- A12) which showed (O–H) stretching absorption near (3330 cm-1) and (C=O) stretching band at (1660 cm-1). UV spectrum of compounds (A4-A12) mostly showed intense maxima at (204 nm) and (339 nm) refering to π→π* and n→π* electronic transition respectively. 191 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Treatment of above Schiff bases with benzoyl chloride in benzene led to open double bond and gives compounds (A13-A21). The IR spectra of these derivatives showed the (C=O) stretching band at (1699 cm-1). UV spectrum of these compounds (A13-A21) showed intense at (232 -236 nm) and (303 - 322 nm) due to π→π* and n→π* electronic transitions. Also the compounds (A22-A30) were prepared by the reaction of compounds (A13-A21) with thiourea and a good yields were achieved. The spectram showed (NH2) stretching band near (3171-3108 cm-1) and (C=O) stretching band at (1685 cm-1). UV spectrum of these derivatives showed intense maxima at (205 -221 nm) and (309 - 382 nm) which belonged to π→π* and n→π* transitions. The imide compounds (A31-A36) were synthesized by the reaction of 2-Amino-5-aryl- 1,3- thiazole-4-carboxylic acid (A1-A3) with maleic anhydride and phthalic anhydride respectively. The IR spectra of these derivatives showed disappearing of (N–H) band and the (C=O) stretching band at (1856, 1778 cm-1). UV spectrum of these derivatives showed intense maxima at (324 -239 nm) and (221 - 203 nm) which belonged to π→π* and n→π* transitions. Spectral data were listed in (table 3). Biological screening: antimicrobial activity tests The antibacterial activities of compounds (A1-A36) were tested against the micro-organisms. After incubation, the diameters of inhibition zones around the wells were measured, to the nearest mm, in three different directions using a ruler and the average diameter was recorded and compared to that of the control. From the data presented in Table 3 it is clear that compounds A10 and A24 were moderately active against Pseudomonas aeruginosa, while A12 was also moderately active but against Proteus vulgaris microorganisms. Generally, other derivatives were slightly active against Staphylococcus epidermidis, Proteus vulgaris, and Pseudomonas aeruginosa. Finally, some compounds were found to be inactive. References 1- Yamane, T.; Mitsudera, H. and Shundoh,T. (2004) Highly regioselective direct halogenation: a simple and efficient method for preparing 4-halomethyl-5-methyl-2- aryl-1,3- thiazoles", Tetrahedron Letters, 45: 69–73. 2- Karabasanagouda, T.; Adhikari, A.V.; Dhanwad, R. and Parameshwarappa, G. (2008) "Synthesis of some new 2-(4-alkylthiophenoxy)-4-substituted-1,3-thiazoles as possible anti- inflammatory and antimicrobial agents", Indian Journal of Chemistry, 47B: 144-153. 3- Cherkupally, S.R.; Dasari, C.R.; Vookanti, Y. and Adki, N. (2010) Synthesis and antimicrobial study of bis-[thiadiazol-2-yltetrahydro-2H-pyrazolo[3,4-d][1,3]thiazole] methanes Org. Commun., 3(3): 57-69,. 4- Thomae, D. and others (2009) One-pot synthesis of new 2,4,5-trisubstituted 1,3-thiazoles and 1,3-selenazoles, Tetrahedron, 65: 2982–2988. 5- Grubb, A.M. (2011) Preparation of Heteroatom- Substituted 1,3-Thiazoles as Bulding Blocks for Liquid Crystal Synthesis , thesis submitted to Kent State University, PhD.. 6- Mobinikhaledi, A.; Jabbapour, M. and Hamta, A. (2011) Synthesis of Some Novel and Biologically Active Schiff Bases Bearing a 1,3,4-Thiadiazole Moiety Under Acidic and PTC Conitions , J. Chil. Chem. Soc., 56(3): 812-814. 7- Joshi, S.D.; Vagdevi, H.M.; Vaidya, V.P. and Gadaginamath, G.S. (2008) Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents, European Journal of Medicinal Chemistry, 43: 1989-1996. 8- Jarrahpour, A. A. and Zarei, M. (2003) Synthesis of 2-({[4-(4-{[(E)-1-(2 hydroxy-3- methoxyphenyl)methylidene amino}phenoxy)phenyl imino}methyl)- 6 -methoxy phenol", Molbank, M352: 1422-8599. 192 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 9- Thanh, N.D. (2012)Synthesis of Peracetylated-D-Glucopyranosyl Thioureas from Substituted 2-Aminobenzo-1, 3-thiazoles", E-Journal of Chemistry, 9(1): 55-62. 10- Xuan, R.; Hu, W. and Yang, Z. (2003) One-Pot Synthesis of dl-2-Amino-2-thiazoline-4- carboxylic Acid", An International Journal for Rapid Communication of Synthetic Organic Chemistry , 33(7): 1109-1112. 11- Alwan, S.M. (2012) Synthesis and Preliminary Antimicrobial Activities of New Arylideneamino-1,3,4-thiadiazole-(thio/dithio)-acetamido Cephalosporanic Acids, Molecules, 17: 1025-1038. 12- Abd-dull Hamid, S. (2010) Synthesis and Characterization of some new Chalconea , Schiff`s bases and NEW azo Compounds, Thesis presented for Ph.D. degree in organic chemistry, University of Tikrit, College of Science. 13- Kandalintseva, N.V.; Prosenko, A.E.; Dyubhenko,O.I. and Stoyanov, E.S. (2001) Synthesis of S-Alkylisothiuronium Halides by Reaction of thiourea with ω-(4- Hydroxyaryl)alkyl Halides, Russian Journal of organic chemistry, 37(9): 1249-1252. 14- Lamani, K. S. and Kotresh, O. (2010) Synthesis and Biological Activity of Some Novel4- (5-Mercapto-1,3,4-thiadiazol-2-yl)-2-phenyl-5-[2-phenylvinyl]-2,4-dihydro-3H-1,2,4-triazol- 3-one, E-Journal of Chemistry, 7(2): 545-550. NH2 NH2 S NH2 NH SH Ar H O NH2 NH SH + Ar H O - SH + NH2 NH Pt. Ar H OH S NH2 NH (Cl)2CH-COOH .. Ar H OH S NH2 + NH CH COOH Cl Ar H OH S NH NH CH COOH Cl -HCl Ar H OH S N NH CH COOH -H2O S N NHAr HOOC Tout. S N NH2Ar HOOC Mechanisem of synthesis supstrate (A1-A3) 193 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Table (1): Physical properties for compounds which have structure: S N R Ar COOH No. of Comp Ar R Molec.Formula Y. % Pur.Solv. MP.ºC A1 o-NO2C6H4– –NH2 C10H7N3O4S 80 Ethanol 218-222 A2 p-(CH3)2NC6H4– –NH2 C12H13N3O2S 85 Ethanol 208-211 A3 p-BrC6H4– –NH2 C10BrH7N2O2S 83 Ethanol 172-175 A4 o-NO2C6H4– o-NO2C6H4CH=N– C17H10N4O6S 75 EtOH+Dw 140-145 A5 o-NO2C6H4– p-BrC6H4CH=N– C17BrH10N4O6S 77 EtOH+Dw 155-159 A6 o-NO2C6H4– p-(CH3)2NC6H4CH=N– C19H16N4O4S 82 EtOH+Dw 211-214 A7 p-(CH3)2NC6H4– o-NO2C6H4CH=N– C19H16N4O4S 85 EtOH+Dw 190-193 A8 p-(CH3)2NC6H4– p-BrC6H4CH=N– C19BrH16N3O2S 87 EtOH+Dw 157-161 A9 p-(CH3)2NC6H4– p-(CH3)2NC6H4CH=N– C21H22N4O2S 88 EtOH+Dw 172-176 A10 p-BrC6H4– o-NO2C6H4CH=N– C17BrH10N4O6S 78 EtOH+Dw 240-243 A11 p-BrC6H4– p-BrC6H4CH=N– C17Br2H10N2O2S 72 EtOH+Dw 195-198 A12 p-BrC6H4– p-(CH3)2NC6H4CH=N– C19BrH16N3O2S 86 EtOH+Dw 185-188 A13 o-NO2C6H4– o-NO2C6H4CH(Cl)N(C(O)C6H5)- C24ClH15N5O6S 58 Benzene 170-172 A14 o-NO2C6H4– p-BrC6H4CH(Cl)N(C(O)C6H5)- C24BrClH15N5O6S 56 Benzene 131-134 A15 o-NO2C6H4– p-(CH3)2NC6H4CH(Cl)N(C(O)C6H5)- C26ClH21N4O5S 66 Benzene 167-170 A16 p-(CH3)2NC6H4– o-NO2C6H4CH(Cl)N(C(O)C6H5)- C26ClH21N4O5S 65 Benzene 144-147 A17 p-(CH3)2NC6H4– p-BrC6H4CH(Cl)N(C(O)C6H5)- C26BrClH21N3O3S 62 Benzene 58-61 A18 p-(CH3)2NC6H4– p-(CH3)2NC6H4CH(Cl)N(C(O)C6H5)- C28ClH27N4O3S 69 Benzene 247-250 A19 p-BrC6H4– o-NO2C6H4CH(Cl)N(C(O)C6H5)- C24BrClH15N4O7S 57 Benzene 228-230 A20 p-BrC6H4– C6H4CH(Cl)N(C(O)C6H5)- C24Br2ClH15N2O3S 35 Benzene 68-71 A21 p-BrC6H4– p-(CH3)2NC6H4CH(Cl)N(C(O)C6H5)- C26BrClH21N3O3S 61 Benzene 163-165 A22 o-NO2C6H4– o-NO2C6H4CH(SC(NH)NH2)N(C(O)C6H5)- C25H18N6O7S2 70 Ethanol 96-98 A23 o-NO2C6H4– p-BrC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C25BrH18N6O7S2 73 Ethanol 148-151 A24 o-NO2C6H4– p-(CH3)2NC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C27H24N6O5S2 69 Ethanol 154-157 A25 p-(CH3)2NC6H4– o-NO2C6H4CH(SC(NH)NH2)N(C(O)C6H5)- C27H24N6O5S2 70 Ethanol 78-81 A26 p-(CH3)2NC6H4– p-BrC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C27BrH24N5O3S2 67 Ethanol 110-113 A27 p-(CH3)2NC6H4– p-(CH3)2NC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C29H30N6O3S2 62 Ethanol 205-208 A28 p-BrC6H4– o-NO2C6H4CH(SC(NH)NH2)N(C(O)C6H5)- C25BrH18N6O7S2 74 Ethanol 168-163 A29 p-BrC6H4– p-BrC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C25Br2H18N3O3S2 71 Ethanol 168-171 A30 p-BrC6H4– p-(CH3)2NC6H4CH(SC(NH)NH2)N(C(O)C6H5)- C27BrH24N4O3S2 68 Ethanol 199-202 A31 p-(CH3)2NC6H4– N O O C16H13N3O4S 78 EtOH+Dw 174-176 A32 p-BrC6H4– N O O C14BrH7N2O4S 75 EtOH+Dw 142-144 A33 o-NO2C6H4– N O O C14H7N3O6S 71 EtOH+Dw 131-133 A34 p-(CH3)2NC6H4– N O O C20H15N3O4S 80 EtOH+Dw 166-168 A35 p-BrC6H4– N O O C18BrH9N2O4S 79 EtOH+Dw 187-189 A36 o-NO2C6H4– N O O C18H9N3O6S 73 EtOH+Dw 234-236 194 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Table (2): Result of antimicrobial activity tests (agar diffusion method) of compounds (A1-A36) Test microorganisms S. albus P. vulgaris Ps Test compounds Average inhibition zone diameter in mms Cefotaxime >23 >26 >16 Penicillin >29 – – Ceftazidime >18 15-17 >16 A1 – 1.8 0.2 A2 0.6 – 1.7 A3 – 2.2 – A4 – 2.1 2.3 A5 1.6 – 2 A6 0.5 1.7 – A7 – 6.1 1.3 A8 3.3 – 4 A9 2.5 4.9 – A10 – – 15.2 A11 – 3.3 7.1 A12 – 14 – A13 0.9 – – A14 6 – – A15 – 7 – A16 3.1 – 5.6 A17 1.9 5.2 3 A18 0.7 – – A19 – 9 0.1 A20 5.4 4 0.6 A21 3.7 – – A22 1 2.2 2 A23 – 3.6 – A24 – 4.8 16 A25 – 1.9 – A26 – – – A27 7.2 – 4.3 A28 0.2 6 5.2 A29 – 2 – A30 – – 1 A31 0.4 – – A32 – – 1.4 A33 6 3.9 2.6 A34 – 1.5 – A35 2.8 – – A36 – – – DMSO 17 20 13 S. albus: Staphylococcus epidermidis; P.vulgaris: Proteus vulgaris; Ps: Pseudomonas aeruginosa. 195 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 Table (3): IR and UV spectral data for compounds (A1 – A36) No. of Comp U.V/ λmax (CHCl3) Characteristic IR bands Cm-1 C=O C–H al. C–H ar. C=N C=C O–H N–H Other A1 227,369 1697 – – 1646 1527 3308 3186-3108 1346(NO2) A2 228,275,370 1660 2906-2820 3049 1599 1537 3421 3309 – A3 233,279,380 1672 – 3051 1627 1525 3375 3275-3173 667 (C–Br) A4 215,240,339 1660 2997 3049 1593,1602 1550 3200 – 1371(NO2) A5 222,241,211,340 1660 2904 3080 1595,1600 1548 3220 – 1425(NO2) 653 (C–Br) A6 211,215,240,339 1660 2906-2818 3090 1595,1610 1550 3330 – 1433(NO2) A7 212,215,240,340 1687 2916-2820 3060 1597,1600 1533 3165 – 1373(NO2) A8 222,226,244,340 1693 2926-2854 3090 1612,1587 1589 3301 – 639 (C–Br) A9 204,222,226,244,340 1693 2926-2854 3072 1612,1592 1527 3210 – – A10 339, 240, 214 , 209 1688 2944 3056 1605,1599 1533 3170 – 1379(NO2) 649 (C–Br) A11 320,289, 216, 210 1660 2713 3010 1626,1580 1527 3215 – 685 (C–Br) A12 359,235,223,207 1652 2800 2720 3002 1622,1592 1550 3230 – 643 (C–Br) A13 311,239 1664,1675 2890 3050 1597 1544 3300 – 1344(NO2) 673 (C–Cl) A14 322,202 1716,1680 2875 3093 1591 1550 3380 – 1350(NO2) 667 (C–Br) 700 (C–Cl) A15 305, 203 1707,1683 2820 3050 1606 1585 3377 – 1338(NO2) 682 (C–Cl) A16 308,223 1662,1670 2821 3011 1599 1533 3270 – 1373(NO2) 713 (C–Cl) A17 310,238 1790,1685 2827 3003 1599 1550 3265 – 667 (C–Br) 707 (C–Cl) A18 355,292 1705,1690 2827 3070 1599 1552 3398 – 707 (C–Cl) A19 309,222, 216 1743,1699 2854 3000 1604 1527 3380 – 1398(NO2) 636 (C–Br) A20 254,238 1753,1681 2987 3000 1601 1514 3337 – 617(C–Br) 783 (C–Cl) A21 302,239 1783,1665 2959 3005 1644 1549 3299 – 659(C–Br) 732 (C–Cl) A22 314,238 1707,1689 2946 3058 1595 1506 3340 3253,3146 1445(NO2) A23 277,213 1710,1691 2999 3095 1612 1527 3381 3275,3173 1413(NO2) 516 (C–Br) A24 228,202 1744,1667 2938 3002 1585 1519 3310 3288,3186 1459(NO2) A25 275,239 1759,1689 2946 3006 1572 1537 3279 3209,3172 1450(NO2) A26 303,218 1700,1691 2800 3025 1610 1535 3371 3271,3161 634 (C–Br) A27 252,201 1708,1650 2998 3000 1608 1500 3358 2271,3161 – A28 298,214 1715,1697 2928 3034 1610 1525 3381 3267,3167 1473 (NO2) 679 (C–Br) A29 331,218 1742,1694 2866 3090 1627 1523 3339 3279,3134 659 (C–Br) A30 254,204 1699,1685 2916 3007 1610 1546 3342 3333,3171 650 (C–Br) A31 304,212 1856,1778 2880 3080 1597 1513 3414 – – A32 324,221 1866,1781 2950 3053 1600 1523 3420 – 665 (C–Br) A33 239,203 1873,1795 2926 3090 1612 1527 3350 – 1460 (NO2) A34 281,217 1876,1734 – 3041 1630 1494 3338 – – A35 299,205 1868,1748 – 3025 1627 1477 3394 – 655 (C–Br) A36 245,207 1881,1703 – 3036 1614 1460 3398 – 1359 (NO2) 196 | Chemistry ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@Ü‹1a26@@ÖÜ»€a@I2@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (2) 2013 ثایوزول -3,1-اریل -5-أمینو -2تحضیر ودراسة الفعالیة ضد البكتریا لمركبات كاربوكسیلیك اسد الجدیدة -4- الدلیميزینھ خضیر أوراس أمین كاظم فرع الكیمیاء الطبیة / كلیة الطب / جامعة واسط عبد الجبار خلف عطیة محمد زبون ثاني قسم الكیمیاء/ كلیة العلوم/ الجامعة المستنصریة 2012كانون األول 30، قبل البحث في : 2012تشرین األول 4استلم البحث في : الخالصة من تفاعل الدیھایدات اروماتیة مختلفة مع ثنائي (A1-A3)كاربوكسیلیك اسد -4-ثایوزول -3,1-اریل -5-أمینو -2ُحّضر (A1-A3)مبتدئا من المركبات االساس (A22-A30)كلورو حامض الخلیك و الثایویوریا. كما ُحّضرت المركبات مع الدیھایدات اروماتیة مختلفة. (A1-A3)المحضرة من تفاعل المركبات (A4-A12)وبخطوتین باستخدام قواعد شف (A34-A36)وانھیدرید الفثالیك (A31-A33) مع انھیدرید المالیك (A1-A3)واخیرا ُحّضرنوعان من االیمایدات من تفاعل واالشعة (FT-IR) بوجود حامض الخلیك الثلجي. ُشّخصت المركبات المحضرة باستخدام طیف االشعة تحت الحمراء ). UV-Visibleفوق البنفسجیة ( كاربوكسیلیك اسد، مشتقات األیمایدات، قواعد شف. -4-ثایوزول -3,1 الكلمات المفتاحیة: 197 | Chemistry