Microsoft Word - 8 Chemistry | 155 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Synthesis, Characterization and Investigation the Antibacterial Activity of New Heterocyclic Compounds Derived From 4-(4`-methoxy benzoyloxy) benzaldehydethiosemicarbazone Nebras M. Jamel Rajaa K. Baker Jumbad H. Tomma Dept. of Chemistry/College of Education for Pure Science (Ibn Al- Haitham)/University of Baghdad Received in:15/May/2016,Accepted in:28/June/2016 Abstract 4-Thiazolidinone were synthesized by three steps,the reaction of ansoyl chloride with 4- hydroxy benzaldehyde to give 4-(4`-methoxy benzoyloxy) benzaldehyde[I].The reaction of later compound with thiosemicarbazideled to formation thiosemicarbazon [II] and the reacted thiosemicarbazone with chloro acetic acid in CH3CO2Na medium to yield 4- thiazelidinone compound[III].The 4-thiazolidinone [III]was used as a key intermediates to synthesis new compounds, compound[IV] synthesized from the reaction [III] with acetic anhydride, while the reaction of compound [III] with amines to yield azo compound[V]a,b,c. The azo compound reacted with benzoyl chloride or anisole chloride in basic medium to get a new esters compound[VI]a,b. Also, synthesis oxazepine compound[VII],[VIII] and [IX]a,b,c from heating schiff bases [III],[IV][V]a,b,c with phthalic anhydride in dry benzene in cyclo-addition reaction. The compounds were characterized by FTIR and 1HNMR (of some of them), the synthesized compounds have been screened for their six species of bacteria were used in this study as tested organisms. These are pseudomonas aeruginosa, klebseilla, providencea, Serratiamarcescens(Gram negative) and staphylococcus epidermidis, Bacillus(Gram positive). Keywords: thiazolidinone, Schiff bass, azo compound, 1,3-oxazepine and antibacterial activity. Chemistry | 156 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Introduction 1,3-Thiazolidin-4-one is five heterocyclic system that has two heteroatoms sulfur and nitrogen at position 1,3 respectively , beside a carbonyl group at position4 [1].Thiazolidin-4- ones are usually synthesized from thiourea, thiosemicarbazides or azomethinegroup[2]. Thiazolidine ring is of considerable interest as it is a structure in various synthetic pharmaceuticals have a broad spectrum of biological activities [3-5]. Oxazepine is unsaturated non-homologous seven membered heterocyclic (containing oxygen at position 1 and nitrogen at position 3 in addition to the five carbon atoms. It is prepared by the pericyclic cycloaddition reaction of schiff bases with a suitable cyclic anhydride carboxylic acid) [6,7]. Oxazepine derivatives was found to exhibit a good variety of biological activities [8]like, anticancer [9], antifungal [10], antibacterial [11] and anticorrosion [12].Azo linkage is considered biological active moiety [13],The most important method for preparing azo compounds via the coupling reaction between diazonium salts and phenols[14 ]. The aim of this work is synthesis of some new oxazepine andthiazolidin4-ones derivatives containing the biologically active azo group, as attempt for increasing the biological activity and its variety. [15] Experimental Chemicals: All chemicals were supplied by fluka, GCC, merek and Aldrich chemicals Co. and used as received. Techniques FTIR spectra were recorded by using KBr disc on a Shimadzo (Ir prestige -21) ¹HNMR spectra were examined by company : Bruker , model: ultra shield 300 MHz , origin : Switzerland and are reported in DMSO as a solvent,ppm(δ), uses TMS as an internal standard were made at chemistry department , Al-Bayt University, Jordan . Hot-Stage, Gallen Kamp melting point apparatus was used for determined uncorrected melting points. Synthesis New compounds are synthesized according to scheme1. Preparation of [4-(4`-methoxy benzoyloxy )benzaldehyde[I] Ansoyl chloride (0.17g, 0.001mol) was added to a stirred solution of 4-hydroxy benzaldehyde (0.12g, 0.001mol) , dry pyridine (1mL) in dimethyl formamide (DMF) (10 mL) at (5-10°C). Stirring was continued for 3hrs (at the same temperature). The resulting mixture was poured onto 20 mL of 10% hydrochloric acid . The precipitate was filtered , washed with solution of 10% NaHCO3 and water for several times ,dried and recrystallized from ethanol.m.p76-780C , yield86% . Synthesis of 4-(4`-methoxybenzoyloxy)benzaldehydethiosemicarbazone [II] A mixture of a suitable aromatic aldehyde [I] (0.256g ,0.001mole) , thiosemicarbazide (0.091g ,0.001mole) in ethanol ( 5mL ) was heated under reflux for 4hrs, then cooled .The off white solid formed was filtered ,dried and recrystallized from ethanol to give compound [III]. m.p200-2020C, yield 97% . Synthesis of 4-(((4-oxothiazolidin-2-ylidene)hydrazono)methyl)phenyl 4- methoxybenzoate[III] A mixture of thiosemicarbazone[II] (0.01mol) ,chloroaceticacide (0.01mol, 0.945g) and fused sodium acetate (0.03mol,2.46g) in absolute ethanol(10 mL) was heated for 6 hrs. The mixture of reaction was poured onto (100 mL) cold water and the precipitate was filtered, washed with water (for many times), recrystallized by ethanol. Chemistry | 157 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Synthesis of 4-(((3-acetyl-4-oxothiazolidin-2-ylidene)hydrazono)methyl)phenyl 4- methoxybenzoate[IV] A solution of compound [III] (3.67g ,0.01mole) in acetic anhydride (25mL)was refluxed for 4hrs, afterward cooled and poured onto ice-water .The resulting was filtered off ,washed with water, dried and recrystallized from ethanol to yield compound [IV]. Scheme (1) Chemistry | 158 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Synthesis of azo derivatives [V]a, b, c This compound was prepared by two main steps: A-Azofization: Into flask was placed in the ice bath (2.1g, 0.02mole) of compound amine dissolved in 12mL of concentrated hydrochloric acide (50%) and the mixture was cooled at (0-5) 0C then added 8mL of a solution contains sodium nitrite(20%) drop by drop to the reaction , that led to formation of diazonium salt in solution. B-Coupling :A mixture of solution (3.67g, 0.01 mole) from compound [III] in 50mL of aqueous solution NaOH (10%) was put into a 250 mL two necked round bottom flask and fitted with thermometer and a dropping funnel and placed in ice bath to be cooled at(0-5) 0C. The cold diazonium solution (step A) was added to the solution (of step B) drop by drop with stirring during two hrs. At the same temperature, we add a solution of HCl 30% to the mixture to form a precipitated compound, which was filtered, washed by cold water and re- crystallized from chloroform. Synthesis of 4-(((5-((4-(benzoyloxy)phenyl)diazenyl)-4-oxothiazolidin-2-ylidene) hydrazono)methyl)phenyl 4-methoxybenzoate and 4-((2-((4-(4-methoxybenzoyloxy) benzylidene)hydrazono)-4-oxothiazolidin-5-yl)diazenyl)phenyl 4-methoxybenzoate [VI]a,b To a stirred solution of compound [V]c (0.47g, 0.001mol), triethylamine(0.2g,0.002mol)in dried mixture of (5mL DMF:10Ml THF), was added drop wise carboxylic acid chloride(0.001mol) at(0-4) 0C. After the addition had been completed the resulting suspension was stirred at the same temperature for 3hrs. The triethylaminehydrochloride salt was precipitate. It was filtered and the filtrate was poured with stirring into 100mL ice-water, then resulting solid was filtered and recrystallized from ethanol. Synthesis of 1,3-oxazepine derivatives [VII],[VIII] and [IX]a,b,c A mixture of compound [III],[IV] or [V]a,b,c (0.48g, 0.001mole) and phthalic acid anhydrides (0.14g, 0.001mol) in dry benzene (3mL) was heating for 6 hrs. The solvent was removed and the resulting colored crystalline solid recrystallized from ethanol. The physical properties for the synthesized compounds are given in Table1. Determination of antibacterial activity Antibacterial activity were detected by agar well diffusion method [16] . Fresh bacterial cultures suspension equivalent of 0.5 tube McFarland turbidity standards (108cfu/ml) were spread on Muller-Hinton agar plates using sterile cotton swabs. Wells of 6mm diameter were cut in solidified agar and filled with 50µl 0f each concentration. The dimethyl sulfoxide was also used as control. The plates were incubated aerobically at 37 0 C for 24 hours, then inhibition zones diameter (mm) around wells were measured by rule. All testes were applied as doublicate. Results and Discussion 4-(4`-methoxybenzoyloxy) benzaldehyde [I] was prepared from reaction of 4-n- alkoxybenzoyl chloride with 4-hydroxy benzaldehyde in dry pyridine and DMF. The FT-IR spectrum of compound [I] showed many bands in the region (2981-2950) cm¯¹ due to υC-H aliphatic stretching, two sharp bands of carbonyl stretching (of ester and aldehyde groups) around 1728 cm¯¹ and 1685 cm¯¹, respectively, besides two stretching bands at 2846 cm¯¹ and 2744 cm¯¹ due to CH aldehydic. Finally, a sharp peak around 1269 cm¯¹ is attributed of υ C-O stretching of ether (OR) group. Chemistry | 159 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Thiosemicarbazone [II] is synthesized by condensation of 4-(4`-methoxy benzoyloxy) benzaldehyde [I] and thiosemicarbazide in ethanol under reflux. FTIR absorption-spectrum of this compound [II] exhibited the disappearance of aldehydic (C=O) and CH absorption bands together with appearance of new absorption stretching band at1695 cm¯¹ which is assigned to υC=N stretching [17]. The spectrum showed many peaks in the region 3441-3088cm-1 which could be attributed to asym. and sym. stretching vibration of NH and NH2 groups [18] besides to two sharp peaks at 1732 cm -1 and 1195cm-1 due to ester and thion bonds, respectively. Compound [III] was synthesized from the condensation of compound [II] with chloroacetic acid (in presence of sodium acetate). The FTIR spectrum showed the appearance of new stretching band due to a carbonyl group of thiazolidinone at 1690cm-1[19]and stretching band appears at 698 cm-1 due to C-S group. While1HNMR spectrum (in DMSO-d as a solvent), Figure (1) showed the following signals: singlet signal at δ (12.28) ppm [20] for one proton of CO- NH (amide) group. Many signals at δ (7.36-8.68) ppm that could be assigned to the eight aromatic protons, but signal at δ (8.1) ppm for a proton of imine, also a singlet signal at δ (3.59) ppm [21] for two protons at C-5 thiazolidinone ring. Finally a singlet signal appeared at δ (4.14) ppm for three protons of OCH3 group. The reaction of thiazolidenone [III] with acetic anhydride yielded a new compound [IV]. This compound is identified by FTIR spectroscopy. The FTIR spectrum of compound [IV] showed disappearance absorption band due to NH group and the appearance of a new band at 1699 cm-1 due to stretching vibration carbonyl for amide group (COCH3). While, the compounds [V]a,b,c were synthesized by the reaction of one mole of compound [III] with two moles of amine with HNO2 at 0-4 0C to get diazonium salt, The FTIR spectrum of this compounds[V]a,b,c showed a stretching band at (1546-1504) cm -1 [22] due to the N=N group, as in Figure (2) of compound [V]c . 1HNMR spectrum of compound [V]b (in DMSO) Figure (3) showed the following characteristics chemical shifts: a singlet signal at δ (3.99) ppm one protons at C-5 thiazolidinone ring, also a singlet signal at δ (4.12) ppm for three protons of OCH3 group and signals in the region δ (7.2-8.3) ppm that due to the eight aromatic protons, another singlet signal appeared at δ (8.35) ppm for a proton of imine, Also a singlet was observed at δ(12.28) ppm for one proton of CO- NH(amide) group. The azo compound [V]c was first converted to ester compounds [VI]a,b by using benzoyl chloride or ansoylchloride in THF and triethyl amine. The ester was identified by FTIR spectra which showed the disappearance of a wide peak around (3442) cm-1 which belongs to stretching vibration of the (-OH) group. The FT-IR spectra also, showed the appearance of the characteristic absorption band at (1732-1724) cm-1[23] due to the stretching vibration of the (C=O) of the forming new ester group. The 1,3-oxazepines[VII], [VIII], [IX]a,b,c were obtained by addition reaction of Schiff bases with naphthalic anhydride in dry benzene. The FTIR absorption bands of these compounds were confirmed from the disappearance of stretching band due to CH=N of Schiff bases with the appearance of two bands characteristic of two carbonyl groups of oxazepine ring in region (1760-1740) cm-1 and (1697-1674) cm-1[24], as in Figure (4) of compound [IX]b. The 1HNMR spectrum of compound [VIII ] , Figure (5) showed twenty aromatic ring protons appear as multiplet in the range (δ 7.01-8.44) ppm, a singlet signal of N-CH proton of oxazepine absorbed at δ 6.87 ppm and two singlet signal at δ(2.3 and 2.2)ppm for two protons at C-5 thiazolidinone ring and COCH3 group, respectively. Furthermore, a singlet signals at δ 4.14ppm for OCH3 protons absorbed. Chemistry | 160 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Biological activity These compounds stabilizer is reasonable biological activity due to presence of either NH or C=O and OH group sinits structure [25]. The cell wall structural nature of gram negative enteric bacteria may be responsible for the observed susceptibility. For instance,( the cell wall of gram negative bacteria contains 15-20% poly saccharides and 10-20% lipid, where gram positive bacteria contain 35-60% poly saccharides and only 0-2% lipid [26]. The poly saccharides and lipid contents of the cell wall affect the permeability of allicin and porrum constituents) [27, 28]. The effect of the prepared compounds was due to interfering with the structure of bacteria cell wall or by stopping bacteria multiplying [29]. All the oxazepine derivatives [X]a-c which were containing azo group show a moderate antibacterial activity against serratiamarcescens, while did not showed any antibacterial activity towards the other types Table (4). Figures (6) exhibited the effect of the synthesized compounds on six types of bacteria. References 1. Jain, K. A.; Vaidya, A.; Ravichandran, V.; Kashaw, K. K. and Agrawal, k. R.( 2012) “Recent development and biological activities of thiazolidinone derivatives”, Bioorg. Med. Chem., xxx-xxx:1-18. 2. 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Sallal, Z. and Ghanem, H.(2011) “Synthesis of New 1,3-Oxazepine Derivatives Containing Azo Group”, Journal of Kufa for Chemical Science, 2:11-23. 8. Abood, H. Z. (2009) “Synthesis of Some New 1,3-Oxazepine and Tetrazole Derivatives Containing Azo Group”, Journal of Kerbala University Scientific,7(1) :297-303. 9. Sunil, D. ;Ranjitha, C. ; Rama, M. and KSR , P. (2014) “Oxazepine Derivative as an Antitumor Agent and Snail1 Inhibitor against Human Colorectal Adenocarcinoma”, International Journal of Innovative Research in Science, Engineering and Technology, 3(8): 15357-15363. 10. AL-rammahi, A. ; AL-Khafagy, A. and AL-rammahi, F.(2015) “Synthesis and Characterization of Oxazepen and Imidazolin Derivatives From 2-Amino-5- Chemistry | 161 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Mercapto-1,3,4- Thiadiazol and Studing of Their Biological Activity” ,World Journal of Pharmaceutical Research, 4(2):1668-1680. 11. Mustafa, A.(2015) “Novel synthesis and antibacterial activities of new derivatives of 7,8-Dichlorodibenzo(b, d)thiophene-2-carboxcyilic acid of pharmaceutical interest”,Diyala Journal For Pure Sciences, 11(1):78-97. 12. Hamak, F. K. and Eissa, H. H.(2013) “Synthesis, Characterization, Biological Evaluation and Anti Corrosion Activity of some Heterocyclic Compounds OxazepineDerivatived from Schiff Bases”,International Journal of ChemTech Research, 5(6): 2924-2940. 13. Pagariya, K.; Pathade, M. and Bodkhe, S.(2015)“Synthesis, Characterization and Antimicrobial screening of some Azo compounds derived from Ethyl vanillin”, Research Journal of Chemical Sciences, 5(7): 20-28. 14. Aljamali, N. (2015) “Review in Azo Compounds and its Biological Activity”, Biochem Anal Biochem.,4(2):1-4. 15. Abood, H. Z. ; Haiwal, T. R. ; ghanim, T. 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(2011) “Synthesis and Characterization of Some New 1,3- Oxazepine Derivatives”, Ibn Al-Haitham Jour. For Pure and Appl. Sci., 24(1) :1-9. Chemistry | 162 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 25. Fahmy, M. M.; Mohamed, R. R. and Mohamed, N. A. (2012) “Novel antimicrobial organic thermal stabilizer and co-stabilizer for rigid pve”, J. Molec ., 17 :7927-7940. 26. Carpenter, P. (1968) “Microbiology” 2nded..PhiladelphiaWB Saunders. 476 27. Nihal, T. Y.; Sedat, V.; Ferda, S. and Gokce, p. (2007) “Effect of extraction conditions on measured total polyphenol contents and antioxidant antibacterial activities of black tea”, Molecules,12:484-496. 28. Alzoreky, N. S. and Nakahara, K. (2003) “Antibacterial activity of extracts from some edible plants commonly consumed in Asia”, Int. J. Food Microbial, 80:223-230. 29. Ahmad, I. and Beg. (2001) “Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multiresistant human pathogens”, J. Ethopharm., 74 :113-123. Table (1) The physical data of compounds [III]-[IX] Comp No. Nomenclature Structural formula Molecular formula M.P ᵒC Yield % Color [III] 4{[(4-oxothiazolidin-2-yli dene)hydrazono-methyl ]phenyl} 4-methoxybenzoate CO2CH3O CH N N N H S O C18H15N3O4S 230-232 96 White [IV] 4-{[(3-acetyl-4-oxothia- zolidin-2-ylidene) hydrazono -methyl]phenyl} 4- methoxybenzoate C20H17N3O5S 210-212 92 Off white [V]a 4-{[(4-oxo-5-(4-tolyldi- azenyl)thiazolidin-2-ylidene) hydrazono-methyl)phenyl 4- methoxybenzoate CO2CH3O CH N N N H S O N N CH3 C25H21N5O4S 195-197 91 Orange [V]b 4-{[(5-((4-methoxyphenyl) diazenyl)-4-oxothiazolidin-2- ylidene)hydrazono-methyl] phenyl} 4-methoxybenzoate CO2CH3O CH N N N H S O N N OCH3 C25H21N5O5S 206-208 99 Brown [V]c 4-{[(5-((4-hydroxyphenyl )diazenyl)-4-oxothiazolidin-2- ylidene) hydrazono-methyl] phenyl}4-methoxybenzoate CO2CH3O CH N N N H S O N N OH C24H19N5O5S 220-222 95 Black [VI]a 4-{[(5-((4-(benzoyloxy) phenyl)diazenyl)-4-oxothia- zolidin-2-ylidene)hydrazono- methyl] phenyl} 4-methoxy benzoate CO2CH3O CH N N N H S O N N O C O C31H23N5O6S 170-172 96 Black [VI]b 4-{[2-(4-(4-methoxybenzoyl- oxy)benzylidene)hydrazono)- 4-oxothiazolidin-5-yl)diazen- yl]phenyl} 4- methoxybenzoate CO2CH3O CH N N N H S O N N O C O O CH3 C32H25N5O7S 198-200 95 Brown Chemistry | 163 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 [VII] 2-[4-(4-methoxybenzoyloxy) phenyl]-3-4-oxothiazolidin-2- ylideneamino)2,3- dihydrobenz [1,2e][1,3]oxazepin-4,7- diones C26H19N3O7S 175-177 64 White [VIII] 2-[4-(4-methoxybenzoyloxy) phenyl]-3(3-acetyl-4- oxothiazolidin-2- ylideneamino)2,3- dihydrobenz [1,2e][1,3]oxazepin-4,7- diones C28H21N3O8S 169-170 63 Off white [IX]a 2-[4-(4-methoxybenzoyloxy) phenyl]-3-[4-oxo-5(4-tolyl) diazenyl)thiazolidin-2-ylidene amino)-2,3-dihydrobenz [1,2e] [1,3]oxazepin-4,7- diones C33H25N5O7S 252-254 58 Pal brown [IX]b 2-[4-(4-methoxybenzoyloxy) phenyl]-3-[4-oxo-5(4- methoxyphenyl)- diazenyl) thiazolidin-2-ylidene amino]- 2,3-dihydrobenz [1,2e] [1,3]oxazepin-4,7-diones C33H25N5O8S >290 42 Gray [IX]c 2-[4-(4-methoxybenzoyloxy) phenyl]-3-{5[(4- hydroxyphenyl) diazenyl)-4- oxo thiazolidin-2-ylidene amino]-2,3-dihydrobenz [1,2e] [1,3]oxazepin-4,7- diones C32H23N5O8S 178-180 58 Dark brown CO2CH3O N N N H S O N N CH3CH O O O CO2CH3O N N N H S O N N OCH3CH O O O CO2CH3O N N N H S O N N OHCH O O O Table (2) Characteristics FTIR absorption bands of compounds[V]a,b,c-[VI]a,b Comp.No Characteristics bands FTIR spectra(cm-1) υ NH υ C-H aliphatic υ C=O υ C=C aromatic υ N=N Other [V]a 3275 2980-2819 1722,1695 1600 1506 δCH3 1371 [V]b 3257 2997-2837 1730,1700 1600 1505 [V]c 3296 2983-2810 1739,1718 1600 1546 υ OH: 3442 [VI]a 3290 2980-2850 1732-1680 1603 1504 [VI]b 3280 2970-2820 1724-1675 1598 1510 Chemistry | 164 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Key of symbols : 1.active(slightly)= + 5 – 10mm,2. active(Moderately)= ++ 11 – 15mm 3. active (Highly) = +++ more than 15mm . Con: DMSO Table (3) Characteristics FTIR absorption bands of compounds[VII],[VIII] and [IX]a,b,c Comp.No. Characteristics bands FTIR spectra(cm-1) υ NH υ C-H aromatic υ C-H aliphatic υ C=O υ C=C aromatic υ C-N [VII] 3323 3076 2966-2848 1755,1720,1693 1595 1356 [VIII] - 3070 2962-2833 1760,1728,1693 1604 1365 [IX]a 3320 3090 2960-2840 1756,1724,1695 1595 1355 [IX]b 3328 3080 2968-2820 1760,1722,1697 1597 1345 [IX]c 3310 3060 2895-2810 1740,1710,1674 1589 1340 Table (4) Antibacterial activity for synthesized compounds providencea klebseilla Pseudomonas- aeruginosa Bacillus Staphylococcus- epidermidis Serratiamarc escens Comp. No. [III] ++ ـــ ++ ـــ ++ ـــ [IV] ـــ ـــ ـــ ـــ ـــ ـــ a[V] ـــ ـــ ـــ ـــ ـــ ـــ b[V] ـــ ـــ ـــ ـــ ـــ ـــ c[V] ـــ +++ ـــ ـــ ++ ـــ a[VI] ـــ ـــ ـــ ـــ ـــ ـــ b[VI] ـــ ـــ ـــ ـــ ـــ ـــ [VII] ـــ ـــ ـــ ـــ ـــ ـــ [VIII] ـــ ـــ ـــ ـــ ـــ ++ ـــ ـــ ـــ ـــ a[IX] ++ ـــ b[IX] ++ ـــ ـــ ـــ ـــ ـــ c[IX] ++ ـــ ـــ +++ ++ ـــ .Con ـــ ـــ ـــ ـــ ـــ ـــ Chemistry | 165 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Figure (2) FTIR-Spectrum of compound [V]c Figure (1) 1HNMR-Spectrum of compound [III] Chemistry | 166 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Figure (4) FTIR-Spectrum of compound [IX]b Figure (3) 1HNMR-Spectrum of compound [V]b Chemistry | 167 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 Figure (6) effect of compounds:[III]-[IX] on bacteria Figure (5) 1HNMR-Spectrum of compound [VIII] Chemistry | 168 2017عام ) 1(العدد 30الھيثم للعلوم الصرفة والتطبيقية المجلد مجلة إبن Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (1) 2017 لمركبات الحلقية غير المتجانسة ل ةالبكتيري الفعالية وتشخيص وفحص تحضير بنزالديھايد ) ميثوكسي بنزويلوكسي– 4` (4من ةمشتقوال الجديدة ثايوسيمكياربزون نبراس مظفر جميل رقرجاء كاظم با جمبد ھرمز توما جامعة بغداد/) الھيثمابن (كلية التربية للعلوم الصرفة /قسم الكيمياء 2016/حزيران/28:قبل في ،2016/أيار/15:فياستلم الخالصة ھيدروكسي بنزالديھايد في خطوة يتكون -4ثايوزولدنون بثالث خطوات من تفاعل انيسول كلورايد مع -4حضر ثايوسيمكاربزايد مع خيرمفاعلة المركب األثم ومن ] [Iبنزايل الديھايد) مثيوكسي بنزويل-4`( -4[خاللھا الديھايد اروماتي و بتفاعل ثايوسيمكياربازون مع كلورو حامض الخليك بوجود خالت الصوديوم يحضر [II]ثايوسيمكاربازون ليعطي مع [III]من تفاعل [IV]حضر مركب جديدةوسطي لتكوين مركبات مركب عملهيست الذي [III]ثايزولدنون -4مركب مركبات االزو مع انيسول كلورايد وبنزويل وعند مفاعلة a,b,c[V]بينما مع االمينات ينتج مركب االزو انھيدريد الخليك و [VII] , [VIII]مركبات اوكسوزبين تحضر. a,b[VI]كلورايد في وسط قاعدي نحصل على مركبات استرية جديدة [IX]a,b,c قواعد شفتفاعل االضافة لمن[III],[IV]و[V]a,b,c شخصت المركبات .ريد نفثالك في البنزين الجافمع انھيد ). لبعض منھال1HNMR (و FTIR, استعمال مطيافيةالمحضرة ب ,pseudomonas aeruginosa, klebseillaوھي ابكتريمن ال انواع ةستضد المركبات المحضرة تم فحص providencea, Serratiamarcescens (Gram negative) وaphylococcusepidermidis, Bacillus(Gram positive) . . ةرييبكتالفعالية الاوكسوزبين و -3,1,مركبات االزو ,قواعد شف , نونيثايوزولد :الكلمات المفتاحية