@1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Synthesis and Study Biological Activity of Some New Isoxazoline and Pyrazoline derivatives Muna S. Al-Rawi Jumbad H. Tomma Dept. of Chemistry/College of Education For Pure Science(Ibn Al- Haitham)/ University of Baghdad Rana M. Abdullah Dept. of Biology/College of Education For Pure Science(Ibn Al- Haitham)/ University of Baghdad Received in : 22 May 2012 , Accepted in: 30 September 2012 Abstract This work involves synthesis of novel Schiff bases derivatives contining isoxazoline or pyrazoline units starting with chalcons . 4-Aminoacetophenone was reacted with 3-nitrobenzaldehyde in basic medium giving chalcone [I] by claisen-schemidt reaction. The chalcone [I] was reacted with hydroxylamine hydrochloride giving isoxazoline [II] in basic medium. The chalcone [I] could also react with hydrazitne hydrate to give pyrazoline [III] . The novel Schiff bases with structural formula [IV] and [V] were prepared by the reaction of amino compounds ; isoxazoline [II] and pyrazolines [III] with p-substituted aldehydes or p-subsituted ketones, respectively in dry benzene using drops of glacial acetic acid as a catalyst with reflux. All the synthesized compounds have been characterized by melting points , FTIR and 1HMNR (of some of theme) spectroscopy. The biological activity of all compounds was examined against antibacterial ; gram(+) and gram(-). Key words : chalcone , pyrazoline , isoxazoline , Schiff bases 208 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Introduction Isoxazoline and pyrazolines derivatives have been reported to possess biological activity[1-4] . In addition, isoxazoline derivatives have played a crucial role as intermediates in the organic synthesis of number of heterocyclic pharmacological active compounds[5]. Various methods are used for the preparation of pyrazolines,among these: Treatment of α,β-unsaturated ketones with hydrazines seems to be the most popular procedure for this purpose. This reaction has been conducted under various conditions[6-9]. Isoxazolines (2)and pyrazolines (3) were prepared from the reaction of chalcones [1] with hydroxylamine hydrochloride in NaOH medium or with hydrazine hydrate , respectively [10] x CH NH2CCH O HN N NH2O2N O N NH2X NH 2 OH . H Cl NH 2 NH 2EtOHOH [2] [1] [3] X= NO2 or Cl Schiff bases attract much interest both for synthetic and biological point of view [11]. A through literature survey revals that Schiff bases derived from various heterocyclic possess cytotoxic [12] , anticonvulsant [13] , antimicrobial [14] , anticancer [15] , and antifungal [16] activities . Depending on the above finding , we decided to synthesize A novel Schiff bases containing isoxazoline or pyrazoline units. Experimental Materials: All the 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 Shimadzo (Ir prestige-21) FTIR spectrophotometer . 1HNMR spectra were carried out by company : Bruker , model: ultra shield 300 MHz , origin : Switzerland and are reported in ppm(δ), DMSO was used as a solvent with TMS as an internal standard . Measurements were made at chemistry department, Al-albyat university , Uncorrected melting points were determined by using Hot-Stage, Gallen Kamp melting point apparatus. General procedures New Schiff bases [IV] and [V] were synthesized according to Scheme 1. Preparation of (chalcone) 4-[3-(3̄-nitrophenyl)-2-propene- 1-one]-aniline [I] Equimolar quantities of 4-amino acetophenone (1.35gm , 0.01mol) and 3- nitrobenzaldehyde (0.01mol) were dissolved in minimum amount of alcohol. Sodium hydroxide solution (0.02 mol) was added slowly and the mixture becomes cold. Then the 209 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 mixture was poured slowly into 400mL of ice water with constant stirring and kept in refrigerator for 24 hrs [17] . The glow yellow solid obtained was filtered ,washed and recrystallized from chloroform . yield (86%) , m.p = 198-200 0C. Preparation of 4[5-(3̄ -nitrophenyl)-4,5-dihydroisoxazol-3-yl ] aniline [II] A mixture of chalcone[I] (0.02mol), hydroxylamine hydrochloride (1.39gm , 0.02mol) and sodium hydroxide solution (0.5gm NaOH in 25mL of water) in ethanol (60mL) were refluxed for 6hrs. The mixture was concentrated under vaccum and poured into ice water . The yellow precipitate obtained was filtered , washed and recrystallized from ethanol .yield (65%), m.p = 130-132 0C. Preparation of 4[5-(3̄ -nitrophenyl)-4,5-dihydro-1H-pyrazol -3-yl]-aniline [III] A mixture of chalcone [I] (0.01mol) and hydrazine hydrate (05gm , 0.01mol ) in ethanol (15 mL) was heated under reflux for 6hrs. After cooling the separated orange solid was filtered off, dried and crystallized from ethanol [18] . yield (75%) ,m.p = 140-142 P0 PC. Synthesis of Schiff bases Amixture of new amino compounds [II] or [III] (0.01 mol) ,different aromatic aldehydes or ketones (0.01 mol), dry benzene (15 mL) and 2drops of glacial acetic acid was refluxed for 3hrs . The solvent was evaporated under vaccum and the residue crystallized from chloroform . The physical data of these Schiff bases are listed in Table 1. C H O NH2CCH3 CH NH2CCH HN N NH2 O N NH2 NH 2 OH . H Cl NH 2 NH 2 EtOH N O N NH C =N A O A (Heterocyclic unit)= OH RC =N AR CORR CORR , Dry benzene G.AA Scheme 1 Dry benzene G.AA NO2 NO2 Base NO2 NO2 O NO2 NO2 [I] [II] [III] [V] [IV] R=4-NO2, 4-Cl, 4-Me2N, 4-Me, 4-Br, 3-NO2, R R R = H or CH3 210 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Results and discussion Chalcone was chosen as the starting material for the synthesis of different heterocyclic compounds , such as : isoxazolines ,pyrazolines derivatives by using approperative reagents for that purpose . The chalcones [I] is synthesized by claisen-schmidt condensation of 4-amino acetophenone and 3-nitrobenzaldehyde by base catalyzed followed by dehydration to yield the desire chalcones. The structural assignments of the chalcones [I] are based on melting points and FTIR spectroscopy. The FTIR spectrum indicated the appearance of two bands in the region (3221- 3425)cm-1 which could be attributed to asymmetric and symmetric stretching vibration of NH2 group,a week band at 3086cm-1 due to stretching vibration of (=C-H) group, two peaks at 1651cmˉ¹ and 1632cmˉ¹ due to of C=O and C=C (CH=CH) stretching vibrations,respectively. Isoxazoline compound [II] was synthesized from the reaction of chalcones [I] with hydroxylamine hydrochloride in alkaline medium. The structure of this compound[II] has been characterized by melting point and FTIR spectroscopy. The FTIR spectra of isoxazoline [II] showed the disappearance of two absorption bands of the CH=CH and C=O group in the starting material [I] together with appearance of new absorption bands for C=N and C-O (cyclic ether) groups around 1610 cmˉ¹ and 1178 cmˉ¹, respectively . The chalcone [I] was further reacted with hydrazine hydrate in ethanol absolute to yield the corresponding pyrazoline derivative. The structure of the pyrazoline [III] was identified by melting point and FTIR spectroscopy. The FTIR spectrum of this compound showed the disappearce of two absorption bands of the CH=CH and C=O group ,in the chalcone [I] and appearance of new absorption bands of NH and C=N group at 3319cmˉ¹ and 1639cmˉ¹ ,respectively. The new Schiff bases [IV] and [V]were synthesized by refluxing aromatic primary amine [II] or [III] and different aromatic aldehydes or aromatic ketones in dry benzene with some drops of glacial acetic acid (GAA). These Schiff bases were identified by their melting points , FTIR and ¹HNMR spectroscopy . FTIR absorption-spectra showed, Figure (1), the disappearance of absorption bands due to NH2 and C=O groups of the starting materials together with appearance of new absorption band in the region (1680-1643)cmˉ¹ which is assigned to C=N stretching. The other data of functional groups which are characteristic of these compounds are given in Table 2. 1HMNR spectrum of Schiff base [V]c , Figure (2), shows the following signals: twelve aromatic protons appeared in the region δ 7.18-8.74 ppm , sharp singlet at δ 11.85 ppm that could be attributed to azomethine protons . A triplet signal at δ 6.80-6.92 ppm is due to one proton of (CH) pyrazoline ring , six protons triplet at δ 3.12 ppm that are attributed to 2CH3 groups . Two protons of CH2 (pyrazoline) appears as doublet at δ 6.54- 6.62 ppm , and a singlet signal at δ 8.74ppm which was assigned to proton of NH group. Biological Activity All the newly synthesized compounds were initially screened for their in vitro antimicrobial activities against the Gram-positive (S. aureus) and the Gram negative (E. coli, K. Pneumoniae, P.aervginosa and Serratia Spp) by disc diffusion. The inhibitory effect of these compounds against these micro-organisms is given in Table 3 . The screening results indicate that some of the compounds exhibit the antimicrobial activity. Each compounds was dissolved in DMSO to give concentration 1ppm. The plates were then incubated at 37 0C and 211 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 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 3. Most of the compounds exhibit the high or low biological activity , the biological activities data are listed in Table 3. References 1- Rao,N. ; Kumar, R. and Srivastava , Y. (2009) “Microwave induced Synthesis and antimicrobial Activies of Some N1-morpholino ethanoyl-3,5-diaryl-2-Pyrazoline derivatives” , Rasayan J.Chem, 2(3) :716-719. 2- Dawane, S. ; Konda, G. ; Shaikh, M. ;Chobe1, S. ; Khandare, T.; Kamble T. and Bhosale , B. (2010) “ Synthesis and Invitro Antimicrobial Activity of Some New 1-thiazolyl-2- Pyrazoline Derivatives ” , Int. J. Pharm.Sci.Rev. Res, 1(2): 3- Jayashankara , B. and Lokanatha Rai , K. (2008) “ Synthesis and Evaluation of Antimicrobial Activity of A New Series of Bis (Isoxazoline) Derivatives ” , Arkivoc , (XI):75- 85 . 4- Azarifar, D. and Shaebanzadeh , M. (2002) “ Synthesis and Characterization of New 3,5- Dinaphthyl Substituted 2-Pyrazolines and Study of Their Antimicrobial Activity” , Molecules, 7:885-895. 5- Caramella, P. and Gruenanger , P. (1984) “1,3-Dipolar Cycloaddition Chemistry” , (Ed.), Padwa, A., Wiley Interscience, New York , 1:337. 6- Azarifar ,D. and Ghasemnejad, H. (2003) “Microwave-Assisted synthesis of some new 3,5-arylated 2-pyrazoline” , Molecules, 8: 642-648. 7- Levai, A. and Jeko, (2007) “synthesis of carboxylic acid derivatives of 2-pyrazolines” , J. Arkivoc, I:134-145 . 8- Li, J. ; Zhang, X. and Lin, Z. (2007) “ an improved synthesis of 1,3,5-triaryl-2-pyrazolines in acetic acid aquieous solution under ultrasound irradiation” , Beilstein Journal of Organic Chemistry, 3(13):1-4. 9- Ramesh ,B.; Prasad, Y. and Ahmed,S. (2009) “ Synthesis and antimicrobial Activity of Some Novel Pyrazoline derivatives” , Pharmacologyonline, 2: 327-330. 10- Khazaal, M. ; Tomma , J. (2011) “Synthesis and Characterization of Novel Schiff Bases Containing Isoxazoline or Pyrazoline Unit” , IBN- AL-Haitham J. For Pure And Appl. Sci. 18 (1): 41-49. 11- Vicini , P. ; Geronikaki , A. ; Incerti , M. ; Busonera , B. ; Ooni , G. Kabras , C. and P. Colla (2003) “ Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases ” , Bioory .Med .Chem . 11:4785-4789. 12- Tarafder , M. ; Kasbollah , A.; Saravan , N.; Crouse , K. ; Ali A. and Tin , O. (2002) “ S- methyldithiocarbazate and its Schiff bases: Evaluation of bondings and biological properties ” , J. Biochem .Mol. Biol. Biophs , 6: 85-91. 13- Satyanarayana , V.; Srevani, P.; Sivakumar, A. and Vijayakumar, V. (2008) “ Synthesis and antimicrobial activity new Schiff bases containing coumarin moiety and their spectral characterization ”, Arkivoc , XVII :221-233. 14- Kahveci , B.; Bekircan, O. and Karaoglu , S. (2005) “ Synthesis and antimicrobial activity of some 3-alkyl-4-(arylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones ”, Indian J. Chem. 44B: 2614-2617. 15- Betircan ,O.; Kahveei, B. and Kucuk , M. (2006) “Synthesis and anticancer evaluation of some new unsymmetrical 3,5-diaryl-4H-1,2,4-triazole derivatives” , Tur . J. Chem. 30:29-40. 16- Singh ,W. and Dash , B. (1988) “Synthesis of some new Schiff bases containing thiazole and oxazole nuclei and their fungicidal activity ” , Pesticides , 22 : 33-37 . 17- Kalirajan , R.; Sivakumar , S. Jubie , S. ; Gowramma, B. and Suresh, B. (2009) “ Synthesis and Biological Evaluation of Some Heterocyclic Derivatives of Chalcones” , International J. of Chem Tech Research 1(1) :27-34. 212 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 18- Abd El-Fattah ,O .; Fathalla , M.; Kassem , E. ; Ibrahem, N. and Kamel , M. (2008) “Synthesis and anticancer of some new quinazolin-4-one derivatives and evaluation of their antimicrobial and Anti-inflammatory effects” ,Acta Poloniae Pharm-Drug Res. 65(1):11-20. Table (1): Physical properties of Schiff bases [IV] and [V] comp. No. Nomencalture Structural Formula Molecular Formula M.P C 0 Yield% Color [IV] a 3[2-chloro benzylidene amino phenyl]-5-(3-̄ nitrophenyl)-4,5- dihydroisoxazole Cl NO2 N O CH=N C22H16N3O3 Cl 100- 102 65 Pale yellow [IV] b 3[3-nitro benzylidene amino phenyl]-5-(3-̄ nitrophenyl)-4,5- dihydroisoxazole O2N NO2 N O CH=N C22H16N3O5 176- 178 67 Dark yellow [IV] c 3[4-N,N-dimethylamino benzylidene amino aniline]-5-(3-̄nitrophenyl )- 4,5-dihydroisoxazole NO2 N O CH=NMe2N C24H22N4O3 154- 156 66 Orange [IV] d 3[4-methoxy-3-hydroxy benzylidene amino phenyl]-5-(3-̄nitrophenyl)- 4,5-dihydro isoxazole HO NO2 N O CH=NCH3O C23H19N3O5 97-99 70 Yellow [IV] e 3[4-methyl benzylidene amino phenyl]-5-(3-̄ nitrophenyl)-4,5- dihydroisoxazole NO2 N O CH=NH3C C23H19N3O3 162- 164 58 Orange- yellow [IV] f 3[4-nitro benzylidene amino phenyl]-5-(3-̄ nitrophenyl)-4,5- dihydroisoxazole O2N NO2 N O CH=N C22H19N4O5 156- 158 66 Pale yellow [IV] g 3[4-chloro benzylidene amino phenyl]-5-(3-̄ nitrophenyl)-4,5- dihydroisoxazole Cl NO2 N O CH=N C22H16N3O3 Cl 122- 124 60 Brown [IV] h 3[4-bromro isomethyl benzyliden amino phenyl]- 5-(3-̄nitrophenyl )-4,5- dihydroisoxazole Br NO2 N O C=N CH3 C23H18N3O3 Br 51-53 58 Pale brown [IV] i 3[4-nitro isomethyl benzylidene amino phenyl]-5-(3-̄nitrophenyl )- 4,5-dihydroisoxazole O2N NO2 N O C=N CH3 C23H18N4O5 74-76 60 Pale Orange [V] a 3[2-chloro benzylidene aminophenyl]-5-(3-̄ nitrophenyl)-4,5-dihydro- 1H- pyrazole Cl NO2 N NH CH=N C22H17N4O2 Cl 118- 120 55 Red- brown [V] b 3[3-nitro benzylidene aminophenyl]- 5-(3-̄nitrophenyl)-4,5- O2N NO2 N NH CH=N C22H17N5O4 150- 152 65 Yellow 213 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 dihydro-1H- pyrazole [V] c 3[4-N,N-dimethyl benzylidene aminoaniline]-5-(3-̄ nitrophenyl)-4,5-dihydro- 1H- pyrazole Me2N NO2 N NH CH=N C24H23N5O2 158- 160 58 Red [V] d 3[4-methoxy-3-hydroxy- benzylidene aminophenyl]-5-(3-̄ nitrophenyl)-4,5-dihydro- 1H- pyrazole CH3O NO2 N NH CH=N HO C23H20N4O4 108- 110 60 Brown [V] e 3[4-methyl benzylidene aminophenyl]- 5-(3-̄nitrophenyl)-4,5- dihydro-1H- pyrazole H3C NO2 N NH CH=N C23H20N4O2 180- 182 55 Orange [V] f 3[4-nitro benzylidene aminophenyl]-5-(3-̄ nitrophenyl)-4,5-dihydro- 1H- pyrazole O2N NO2 N NH CH=N C22H17N5O4 100- 102 65 Red- orange [V] g 3[4-chloro benzylidene aminophenyl]-5-(3-̄ nitrophenyl)-4,5-dihydro- 1H- pyrazole Cl NO2 N NH CH=N C22H17N4O2 Cl 122- 124 58 Brown [V] h 3[4-bromo isomethyl benzylidene aminophenyl]- 5-(3-̄nitrophenyl)-4,5- dihydro-1H- pyrazole Br NO2 N NH C=N CH3 C23H19N4O2 Br 200- 202 50 brown [V] i 3[4-nitro isomethyl benzylidene aminophenyl]- 5-(3-̄nitrophenyl)-4,5- dihydro-1H- pyrazole O2N NO2 N NH C=N CH3 C23H19N5O4 140- 142 55 Orange- red 214 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Table (2): Characteristic FTIR absorption bands of Schiff bases [IV] and [V] Comp. No. νNH νC-H aliph νC=N exocyc. νC=N endocyc. νC=C aromatic others [IV] a 2922-2856 1680 1607 1595 2-Cl:820 [IV] b 2878 1660 1613 1586 3NO2:1504, 1352 [IV] c 2857-2824 1647 1609 1584 4-N(Me) 2: 1346 [IV] d 2890-2837 1690 1620 1592 4-OH:3430 [IV] e 2915-2850 1650 1608 1595 [IV] f 2866 1660 1607 1586 4-NO2:1508, 1321 [IV] g 2922-2857 1657 1607 1590 4-Cl:822 [IV] h 2860-2820 1645 1615 1584 Br : 675 [IV] i 2924-2855 1681 1615 1595 4-NO2:1508,1319 [V] a 3379 2918-2847 1657 1610 1597 2-Cl:806 [V] b 3383 2910-2868 1661 1620 1595 3NO2:1525, 1320 [V] c 3402 2922-2855 1659 1615 1597 4-N(Me) 2: 1313 [V] d 3361 2935-2820 1665 1620 1590 4-OH:3220 [V] e 3360 2920-2851 1693 1607 1595 [V] f 3393 2926-2853 1680 1625 1597 4-NO2:1521, 1319 [V] g 3390 2924-2855 1660 1624 1593 4-Cl:827 [V] h 3390 2903-2830 1653 1624 1597 Br : 678 [V] i 3344 2960-2825 1643 1609 1580 4-NO2:1528,1300 Table (3) : antibacterial activity of the synthesized compounds [II]-[V] Comp. No. Klebsiella Pneumoniae(G-) Pseudomonas aervginosa (G-) Serratia Spp. (G-) E.Coli(G-) Staphlococcus aurus (G+) [II] + + + + + + + + + [III] + + + + + [IV] a + + + + + + + + + + + + + [IV] b + + + + + + + + + [IV] c + + + + + + + + [IV] d - - - + - [IV] e + - + + + [IV] f + + + + + [IV] g + - + + + [IV] h + + + + + + + + + + + + + [IV] i + + + + + + + + + + + + [V] a + - + + + [V] b + + + + + [V] c + + + + + + + + + + [V] d - - - + - [V] e + + + + + + + + + + + + + + + [V] f + + + + + + + [V] g + - + + + [V] h + + + + + + + [V] i + + + + + + + + + + Key to symbols: Highly active = + + +(mor than)15 mm. Moderately active = + +(11-15) mm and slightly active = + (5-10) . 215 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Fig. (1) :FTIR- spectrum of compound [IV]c Fig. (2):1HNMR spectrum of compound [V]c 216 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 بایرازولینوال تحضیر ودراسة السلوك البایولوجي لبعض مشتقات االوكزازولین الجدیدة سعید منى سمیر جمبد ھرمز توما جامعة بغداد / )ابن الھیثم(كلیة التربیة للعلوم الصرفة / الكیمیاء علوم قسم رنا مجاھد عبد هللا جامعة بغداد / )ابن الھیثم(كلیة التربیة للعلوم الصرفة / قسم علوم الحیاة 2012أیلول 30قبل البحث في :، 2012آیار 22استلم البحث في : الخالصة حتوي على حلقات غیر متجانسة متنوعة مثل أوكزازولین ، جدیدة ت یتضمن ھذا البحث تحضیر قواعد شف نایتروبنزالدیھاید -3أمینو اسیتوفینون مع - 4] من تفاعلIبایرازولین باستعمال الجالكون مادة اساسیة ، یحضر الجالكون [ في وسط ] مع ھایدروكسیل أمین ھایدروكلوراید I. یتفاعل الجالكون [شمدت-في وسط قاعدي بوساطة تفاعل كالیسین ] مع الھایدرازین الى I] ، بینما یؤدي تفاعل أحد أ نواِع الجالكونات [IIمؤدیا الى تكوین مشتقات االیزوكزازولین [ قاعدي تجانسة مختلفة ؛ ] من تفاعل مركبات حلقیة غیر مV] و [IVحضرت قواعد شف [ III].تكوین البایرازولین [ ] مع ألدیھایدات او كیتونات متنوعة على التوالي في بنزین جاف وقطرات من III] اوالبایرازولین [IIأوكزازولین [ حامض الخلیك الثلجي مع التصعید العكسي. ائق شخصت جمیع المركبات المحضرة في ھذا البحث من خالل قیاس درجات أنصھارھا فضال عن الطر كما درست .الطیفیة المتمثلة بطیف األشعة تحت الحمراء وطیف الرنین النووي المغناطیسي البروتوني (للبعض منھا) ).-الفعالیة البایولوجیة لجمیع المركبات المحضرة ضد انواع من البكتریا ھي كرام (+) وكرام ( : الجالكون ، االوكزازولین ، البایرازولین ، قواعد شف الكلمات المفتاحیة 217 | Chemistry