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تحضير ودراسة طيفية لمعقدات مزيج الليكاند لايونات بعض العناصر الانتقالية
Author name:
عباس سامي عبد
Supervisor name:
عبد الله محمد علي حبيبان | مسلم حسن محمد
General topic:
Chemistry
Specific topic:
Chemistry
Degree:
Master
University:
University of Al-Qadisiyah - Faculty Of Education - Chemistry Department
Language:
Arabic
University location:
Qadisiyah
First pages:
25T1445 - p.pdf
Abstract:
تضمنت الدراسة تحضير عدد من المشتقات الحلقية غير المتجانسة بالاضافة الى بعض المشتقات ثنائية الاريل والتي تعد ذات اهمية في مجال الكيمياء الطبية ,ونواة لتحضير بعض المشتقات الكيميائية الاخرى للمركب بارا - بروموانيلين والتي درس بعضا منها كمضادات للـ(HIV). وك | A new series of heterocyclic derivatives together with new biaryl analogues of biological interest have been synthesized starting from p - bromoaniline. Most of the new synthesized analogues have been tested for their anti - HIV (anti - human immunodeficiency virus - AIDS) activity.The thesis included the preparation of four types of compounds which have been use for further reactions as followings : 1. Preparation of the analogue R1 and its derivatives from treatment of p - bromoaniline with chloroacetylchloride. Reaction of R1 with KSCN or NH4SCN afforded the analogues R2 and R3 bearing benzothiazole backbone, respectively, while treatment of R1 with thiourea, hydrazine hydrate and piperazine gave R4, R5 and R7, respectively. In addition, treatment of R5 with p - toluenesulphonyl chloride (TsCl) yielded R6, meanwhile, fusion of R7 with maliec and phthalic anhydrides gave R8 and R9, respectively (Scheme 1).2. Preparation of the analogue R10 and its derivatives from treatment of p - bromoaniline with NH4SCN in the presence of bromine. Nucleophilic substitution of bromro residue of R10 by ( - SCN) group under microwave irradiation (MWI) afforded R11. Fusion of the latter with maliec, phthalicand succinic anhydrides gave R12, R13 and R14, respectively. In addition, treatment of R10 with p - cyanophenylboronic acid, via Suzuki coupling reaction and under MW, furnished the analogue R21(Scheme 2).3. Preparation of the analogue R15 and its derivatives,via diazotization reaction, from reaction of p - bromoaniline with acetylacetone. Treatmet of R15 with hydrazine hydrate or phenylhydrazine afforded R16 and R17, respectively.Furthermore, treatment of R17 with substituted arylboronic acids, via Suzuki coupling reaction and under MW, gave R23, R24 and R25 (Scheme 3).4. Preparation of the analogue R15 and its derivatives from treatment of p - bromoaniline with dimethylaminobenzaldehyde to give the azomethane derivative, which has been subjected to reflex with maliec and phthalic anhydrides by using ethanol to give the analogues R19 and R20, respectively. Additionally, treatment of R18 with substituted arylboronic acids, via Suzuki coupling reaction and under MWI, gave R27 and R28 (Scheme 4). The structures of the new synthesized analogues have been assigned from their 1H, 13C NMR and the C.H.N. analysis. In addition, most of the compounds have been identified from their 2D NMR : HSQC, HMBC, COSY and ROESY spectra.The thesis included the biological active study of the most new synthesized derivatives against Human Immunodeficiency Virus (HIV - 1 and HIV - 2) (AIDS), which carried out at Rega medical institute college of medicine, Katholiek University, Leuven, Belgium. The study showed that five analogues exhibited remarkable anti - HIV activity, since the analogues, R6, R8, R13, R26 and R28 showed EC50> (3.19, 2.11, 3.41, 2.31 and 3.72) µg/mL. In conclusion, compound R8 being the agent of choice for further pharmacological evaluation by its structural medication which might optimizeits potential activity to be drug in the future for treatment of AIDS.
