Utilization derivatives of 4 -  [4-(acetylamino)phenyl]-2 - (3,5 dimethyl -  1 H-pyrzol -1-yl)-3-hydroxy-4-oxobutanoic acid in Heterocyclic Synthesis and Study of Their   Biological Activities

مختار المبروك أبورزيزة; خالد الفلوس

doi:10.59743/aujas.v5i2.903

المؤلفون

مختار المبروك أبورزيزة قسم الكيمياء، كلية العلوم، الجامعة الأسمرية الإسلامية، زليتن، ليبيا
خالد الفلوس قسم الكيمياء، كلية العلوم، الجامعة الأسمرية الإسلامية، زليتن، ليبيا

DOI:

https://doi.org/10.59743/aujas.v5i2.903

الكلمات المفتاحية:

acetylamino phenyl ، oxobutanoic acid ، imidazole، thiadiazole ، imidazo thiadiazole، pyridazinon

الملخص

في هذا البحث تم استخدام مشتقات حمض 4 - [4- (أسيتا امينو) فينيل]-2- (5,3- ثنائي ميثيل- 1 H بيرول -1- يل - 3- هيدروكسي -4- اكسوا بيوتا نويك) وذلك من خلال معالجة الحمض مع 35, ثنائي ميثيل 1H - بيرا زول للحصول علي ناتج الاضافة (3) الذي يستخدم لتحضير المركبات الغير متجانسة مثل البيريدازينون والفيورانون. وأثبتت التراكيب البنائية للمركبات المحضرة بواسطة أجهزة التحاليل الدقيقة مثل الأشعة تحت الحمراء والرنين المغنطيسي ومطياف الكتلة. وكانت لها نتائج ايجابية عند اختبارها بيولوجيا على بعض انواع البيكتريا و الفطريات.

المراجع

. Z. Juranic, Lj. Stevovic, B. Drakulic, T. Stanojkovic, S. Radulovic, S. Juranic and I. O. J. Serb. “Substitued (E)-β-(benzoyl)acrylic acids suppressed survival of neoplastic human hela cells”. Chem. Soc., vol.64,p.p 505-512, 1999. DOI: https://doi.org/10.2298/JSC9909505J

. T. F. Pastor and J. B. Drakulic “Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids”. Tetrahedron Letters,vol. 51 p.p 734–738, 2010. DOI: https://doi.org/10.1016/j.tetlet.2009.11.129

. N. Neamati, “Patented small molecule inhibitors of HIV-1 integrase: a 10-year saga”. Expert Opin Therap Patents. vol.12(5), p.p709–724, 2002. DOI: https://doi.org/10.1517/13543776.12.5.709

. A. Billich, Shionogi-GlaxoSmithKline. Curr Opin Investig Drugs.vol. 4, p.p 206–209, 2003.

. M. Cedric, B.Fabrice and C. Philippe “Improved preparation and structural investigation of -aryl-4-oxo-2-hydroxy-2-butenoic acids and methyl esters”. Tetrahedron, vol. 60, p.p 6479–6486,2004. DOI: https://doi.org/10.1016/j.tet.2004.06.030

. S. Toshihiro , M. Minoru , H. Yuji, T.Toshiyuki , S. Takunobu ,O. Osamu , N. Katsumasa ,K. Hidefumi , H. Masayasu, G.Akira , I. Hisashi, I. Akane , K. Akio , F. Takehiro, G. Ying-Duo , Douglas J. MacNeil and Y.Lihu, “Identiﬁcation of novel and orally active spiroindoline NPY Y5 receptor antagonists”. Bioorganic & Medicinal Chemistry Letters, vol. 19, p.p 1564–1568,2009. DOI: https://doi.org/10.1016/j.bmcl.2009.02.035

. S. Nagaaki , j.Makoto, I. Shiho, N. Keita, T. Hiroyasu, A. Makoto, O. Osamu, I. Hisashi, G. Akira, I. Akane, K. Akio, and F. Takehiro , “Discovery of substituted 2,4,4- triarylimidazoline derivatives as potent and selective neuropeptide Y Y5 receptor antagonists”, Bioorganic & Medicinal Chemistry Letters, vol. 19, p.p 1670-1674, 2009. DOI: https://doi.org/10.1016/j.bmcl.2009.01.101

.[8]J. H. Laragh and J.E Sealey, “K+ Depletion and the Progression of Hypertensive Disease or Heart Failure”, Hypertension vol. 37, p.p 806-810, 2001. DOI: https://doi.org/10.1161/01.HYP.37.2.806

. J. H, ragh, Am.J.Hypertens.14,84,2001 DOI: https://doi.org/10.1093/ijl/14.1.84

.[10] M.Epstein, “Aldosterone a mediator of processive renal disease : pathogenic and clinical implication”, Am,J.Kidney Dis.vol. 37, p.p 677-688,2001. DOI: https://doi.org/10.1016/S0272-6386(01)80115-3

.[11] H.C.Korting and M. Schaller “New developments in medical mycology”, Hautarzt vol. 52(2), p.p91-97, 2001. DOI: https://doi.org/10.1007/s001050051271

.[12] A., Hurwitz, C.E. Ruhl, B.F. Kimler, E.M. Topp, M.S Mayo and J. Clin. Pharmacol. “Gastric function in the elderly: effects on absorption of ketoconazole”, vol. 43, p.p 996-1002, 2003. DOI: https://doi.org/10.1177/0091270003255645

.[13]S. Miyamoto,” Molecular modeling and structure based drug discovery studies of aldose reductase inhibitors”,Chem-Bio informatics Journal, vol. 2(3), p.p 74-85, 2002. DOI: https://doi.org/10.1273/cbij.2.74

.[14] A,p.Dariusz, M.B. Andrzej, E.L. Agnieszk, J.S. Bohdan, and K. Jerzy “Synthesis of 1-{4-[4- (adamant-1-yl)phenoxymethyl]- 2-(4-bromophenyl)-1,3-dioxolan-2-ylmethyl}imidazole with expected antifungal and antibacterial activity”, Acta Poloniae Pharmaceutica ñ Drug Research,Vol.64(6) p.p.535-540,2007.

.[15] C.S. Prabodh, V.S. Sunil, J. Sandeep, S. Dalbir, and S. Bhojraj, “Synthesis of some new isoxazoline derivatives as possible anti-candida agents”,Acta Poloniae Pharmaceutica ñ Drug Research, Vol. 66 ( 1), p.p. 101-104, 2009.

.[16] M. Marcin, Z. Michal, T. Magdalena, R. Stanislaw “Synthesis, immunological activity and computational study of 5-amino-3-methyl-4- isoxazolecarboxylic acid semicarbazides and thiosemicarbazide” ,Acta Poloniae Pharmaceutica - Drug Research, Vol. 65 ( 5), p.p. 543-549, 2008.

.[17] M. MARCIN, CZY—SKI, M. ZIMECKI ,and S. RYNG , “New class of isoxazole derivatives: the m 1-9 series of compounds with immunotropic activity”, Acta Poloniae Pharmaceutica ñ Drug Research, Vol. 65 ( 2 ), p.p. 241-244, 2008.

.[18]H.M. Asif and A. Priyanka “2-[3-(4- Chloro/ethyl phenyl)propan -3-one]-5- (substituted phenyl)-1,3,4-oxadiazoles: synthesis and biological evaluation”, Acta Poloniae Pharmaceutica - Drug Research, Vol. 65 ( 5), p.p. 527-534, 2008.

.[19]I. Mojahidul, A.S. Anees, R.RamadosS, B. Afroz, and G.Sunil “Synthesis and antimicrobial activity of some novel oxadiazole derivatives”; Acta Poloniae Pharmaceutica - Drug Research, Vol. 65 ( 4), p.p. 441-447, 2008.

.[20]T. Nazar, D. Maria and J.I Ewa “Cyclization of thiosemicarbazide derivatives of5-arylidene-2,4-dioxothiazolidine-3-acetic acids to1,3,4-thiadiazoles and their pharmacological properties”, Acta Poloniae Pharmaceutica - Drug Research, Vol. 64 ( 3 ), p.p. 227-231, 2007.

.[21]Ø.Justyna, O. Dorota Z. Zofia A. Ewa andZ. Lucjusz, “Synthesis of2,3-dihydro-7-nitroimidazo [5,1-b]oxazole as potential tuberculostatic agents”, Acta Poloniae Pharmaceutica - Drug Research, Vol. 65 ( 2 ), p.p. 229-233, 2008.

.[22]S.A.Rizk , M.A.El-Hashash and M.M.Aburzeza, “ 1,4-Arylation of β-(4-acetylaminobenzoyl)acrylic acid with activated aromatic hydrocarbons under fridel-crafts conditions and some studies with the products” ,Egypt.J.Chem.vol. 54(1), p.p 75-85, 2011. DOI: https://doi.org/10.21608/ejchem.2011.1380

.[23]S. A.Rizk and M. A. El-Hashash”2-(3,4-Dimethylphenyl-[3,4-dichloro (or 3,4-dimethyl) benzoyl) -propanoic acids as precursors in the synthesis of some heterocyclic compounds” Egypt.J.Chem.,vol.54,p.p 1-5,2011. DOI: https://doi.org/10.21608/ejchem.2012.1427

.[24]S.A. Rizk, M..A.EL-Hashash and M..M.Aburzeza; “Utility of p-acetamidobenzoyl prop-2enoic acid in the synthesis of new α-amino acids and using them as building blocks in heterocyclic synthesis”, Egypt. J.Chem., vol. 54(3), 2011. DOI: https://doi.org/10.21608/ejchem.2011.1396

.[25] S.A. Rizk, M.A.El-Hashash, and K.K. Mostafa, “ Utility of β -aroyl acrylic acid in heterocyclic synthesis”,Egypt, J. Chem. ,vol. 51 (5) , p.p 116-121,2008.

.[26]M. El-Kadi, M.A. El-Hashash and M.A.,Sayed, “Action of hydrazine,amine and thiourea upon 3-(4-chloro-3-methyl)benzoyl acrylic acid” Revue Roumaine de Chimie, vol. 26 (8), p.p 1161-1167, 1981. DOI: https://doi.org/10.1002/chin.198151204

.[27]M.A. El-Hashash and M. El-Kady ”Some reactions of 3-aroyl acrylic acid epoxides”Revue Roumaine de Chimie. 23 11-12,1581-1588 1978.

.[28] O. A.Attanasi, P. Filippone and P. Synlett, “ Working twenty years on conjugated azo alkenes (and environs) to find new entries in organic synthesis” Synlett , p.p 1128–1140, 1997. DOI: https://doi.org/10.1055/s-1997-973

.[29]O. A. Attanasi, L. De. Crescentini, p. Filippone, F. Mantellini, and F. Santeusanio, “1,2-Diaza-1,3-butadienes; just a nice class of compounds, or powerful tools in organic chemistry? reviewing an experience”, Arkivoc, vol. ( xi), p.p 274–292,2002. DOI: https://doi.org/10.3998/ark.5550190.0003.b25