Synthesis, Characterization and Study the Biological Activity of Some New Heterocyclic Compounds Derived from Terephthalic Acid
الموضوعات :
Eman M. Hussain
1
,
Rajaa K. Baqir
2
,
Jumbad H. Tomma
3
1 - Department of Chemistry, College of Education for Pure Science (Ibn-Al Haitham), University of Baghdad, Baghdad, Iraq
2 - Department of Chemistry, College of Education for Pure Science (Ibn-Al Haitham), University of Baghdad, Baghdad, Iraq
3 - Department of Chemistry, College of Education for Pure Science (Ibn-Al Haitham), University of Baghdad, Baghdad, Iraq
تاريخ الإرسال : 10 الثلاثاء , جمادى الثانية, 1444
تاريخ التأكيد : 01 الثلاثاء , شعبان, 1444
تاريخ الإصدار : 17 الجمعة , جمادى الأولى, 1445
الکلمات المفتاحية:
Thiourea derivatives,
Schiff bases,
Terephthalic acid,
imidazole,
Acid hydrazide,
ملخص المقالة :
The organic compound imidazole has the chemical formula C3N2H4. Numerous significant biological compounds contain imidazole. The amino acid histidine is the most prevalent. The substituted imidazole derivatives have great potential for treating a variety of systemic fungi infections. Thiourea is an organosulfur compound with the formula SC(NH2)2. It is a reagent in organic synthesis. In this paper, some new imidazole and thiourea derivatives are synthesized, characterized, and studied for their biological activity. These new compounds were synthesized from the starting material terephthalic acid, which was transformed to corresponding ester [I] by the refluxing of diacid with methanol in the presence of H2SO4 as a catalyst, compound [I] condensation with hydrazine hydrate 80% to yielded acid hydrazide [II], which was refluxed with 2 moles of various aromatic aldehydes in the presence of few drops of glacial acetic acid as a catalyst to yielded Schiff bases . Refluxing of chosen derivative with acetyl chloride in dry benzene gave new acetyl compounds which were reacted with thiourea and anhydrous sodium carbonate with acetone as a solvent to give new thiourea derivatives . Compounds were used to synthesize new imidazole derivatives by the reaction of appropriate compound with 2 moles of benzoin in dry DMF under cyclization reaction. FTIR, 1HNMR, and mass spectroscopy are used to characterize the synthesized compounds.
المصادر:
Soni J., Sethiya A., Sahiba N., Agarwal D.K., Agarwal S., 2019. Contemporary progress in the synthetic strategies of imidazole and its biological activities. Current Organic Synthesis. 16(8), 1078–1104.
Beltran-Hortelano I., Alcolea V., Font M., Pérez-Silanes S., 2020. The role of imidazole and benzimidazole heterocycles in Chagas disease: A review. European Journal of Medicinal Chemistry. 206 112692.
Zięba S., Dubis A.T., Gzella A.K., \Lawniczak P., Pogorzelec-Glaser K., Lapiński A., 2019. Toward a new type of proton conductor based on imidazole and aromatic acids. Physical Chemistry Chemical Physics. 21(31), 17152–17162.
Shabalin D.A., Camp J.E., 2020. Recent advances in the synthesis of imidazoles. Organic & Biomolecular Chemistry. 18(21), 3950–3964.
Munk S.A., Harcourt D., Ambrus G., Denys L., Gluchowski C., Burke J.A., Kharlamb A.B., Manlapaz C.A., Padillo E.U., Runde E., 1996. Synthesis and Evaluation of 2-[(5-Methylbenz-1-ox-4-azin-6-yl) imino] imidazoline, a Potent, Peripherally Acting α2 Adrenoceptor Agonist. Journal of Medicinal Chemistry. 39(18), 3533–3538.
Siwach A., Verma P.K., 2021. Synthesis and therapeutic potential of imidazole containing compounds. BMC Chemistry. 15(1), 1–69.
Muslim R.F., Majeed I.Y., Saleh S.E., Saleh M.M., Owaid M.N., Abbas J.A., 2022. Preparation, Characterization and Antibacterial Activity of some New Oxazolidin-5-one Derivatives Derived from Imine Compounds. Journal of Chemical Health Risks. 12(4), 725–732.
Tolomeu H.V., Fraga C.A.M., 2023. Imidazole: Synthesis, Functionalization and Physicochemical Properties of a Privileged Structure in Medicinal Chemistry. Molecules. 28(2), 838.
Xue Y., Zhao G., Yang R., Chu F., Chen J., Wang L., Huang X., 2021. 2D metal–organic framework-based materials for electrocatalytic, photocatalytic and
thermocatalytic applications. Nanoscale. 13(7), 3911–3936.
Khandelwal S., Tailor Y.K., Rushell E., Kumar M., 2020. Use of sustainable organic transformations in the construction of heterocyclic scaffolds, in Green Approaches in Medicinal Chemistry for Sustainable Drug Design, Elsevier. p. 245–352.
Yilmaz B., 2019. Isocyanide synthesis by using formamides obtained by applying the Leuckart-Wallach approach, PhD Thesis.
Ovonramwen O., Owolabi B., Philip Oviawe A., Falodun A., 2020. Synthesis and Antimicrobial Activity of 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl-8-Quinolinoxide. Journal of Chemical Health Risks. 10(3), 233–242.
Bokale-Shivale S., Amin M.A., Sawant R.T., Stevens M.Y., Turanli L., Hallberg A., Waghmode S.B., Odell L.R., 2021. Synthesis of substituted 3, 4-dihydroquinazolinones via a metal free Leuckart–Wallach type reaction. RSC Advances. 11(1), 349–353.
Ramaiah M.M., Shubha P.B., Prasad H., Shivananju N.S., 2020. Novel synthesis of N-unsubstituted imidazoles via the cycloaddition of N-(tert-butylsulfinyl) imines and TosMIC. Tetrahedron Letters. 61(14), 151705.
Rudy H.K.A., Mayer P., Wanner K.T., 2020. Synthesis of 1, 5-Ring-Fused Imidazoles from Cyclic Imines and TosMIC–Identification of in situ Generated N-Methyleneformamide as a Catalyst in the van Leusen Imidazole Synthesis. European Journal of Organic Chemistry. 2020(24), 3599–3612.
Love B.E., 1996. Synthesis of β-carbolines. A review. Organic Preparations and Procedures International. 28(1), 1–64.
Sharma P., LaRosa C., Antwi J., Govindarajan R., Werbovetz K.A., 2021. Imidazoles as potential anticancer agents: An update on recent studies. Molecules. 26(14), 4213.
Ali I., Lone M.N., Aboul-Enein H.Y., 2017. Imidazoles as potential anticancer agents. MedChemComm. 8(9), 1742–1773.
Wan Y., Fang J., Wang Y., Sun J., Sun Y., Sun X., Qi M., Li W., Li C., Zhou Y., 2021. Antibacterial zeolite imidazole frameworks with manganese doping for immunomodulation to accelerate infected wound healing. Advanced Healthcare Materials. 10(22), 2101515.
Valls A., Andreu J.J., Falomir E., Luis S.V., Atrián-Blasco E., Mitchell S.G., Altava B., 2020. Imidazole and imidazolium antibacterial drugs derived from amino acids. Pharmaceuticals. 13(12), 482.
Rocha T.M., Machado N.J., Sousa J.A.C. de, Araujo E.V.O., Guimaraes M.A., Lima D.F., Leite J.R. de S. de A., Leal L.K.A.M., 2019. Imidazole alkaloids inhibit the pro-inflammatory mechanisms of human neutrophil and exhibit anti-inflammatory properties in vivo. Journal of Pharmacy and Pharmacology. 71(5), 849–859.
Alghamdi S.S., Suliman R.S., Almutairi K., Kahtani K., Aljatli D., 2021. Imidazole as a promising medicinal scaffold: Current status and future direction. Drug Design, Development and Therapy. 15 3289.
Adeyemi O.S., Eseola A.O., Plass W., Kato K., Otuechere C.A., Awakan O.J., Atolani O., Otohinoyi D.A., Elebiyo T.C., Evbuomwan I.O., 2021. The anti-parasite action of imidazole derivatives likely involves oxidative stress but not HIF-1α signaling. Chemico-Biological Interactions. 349 109676.
Adeyemi O.S., Eseola A.O., Plass W., Atolani O., Sugi T., Han Y., Batiha G.E., Kato K., Awakan O.J., Olaolu T.D., 2020. Imidazole derivatives as antiparasitic agents and use of molecular modeling to investigate the structure–activity relationship. Parasitology Research. 119(6), 1925–1941.
Günsel A., Taslimi P., Atmaca G.Y., Bilgicli A.T., Pişkin H., Ceylan Y., Erdoğmuş A., Yarasir M.N., Gülçin İ., 2021. Novel potential metabolic enzymes inhibitor, photosensitizer and antibacterial agents based on water-soluble phthalocyanine bearing imidazole derivative. Journal of Molecular Structure. 1237 130402.
Chaudhry F., Shahid W., Al-Rashida M., Ashraf M., Munawar M.A., Khan M.A., 2021. Synthesis of imidazole-pyrazole conjugates bearing aryl spacer and exploring their enzyme inhibition potentials. Bioorganic Chemistry. 108 104686.
Vogel P., Houk K.N., 2019. Organic Chemistry: Theory, Reactivity and Mechanisms in Modern Synthesis. John Wiley & Sons. 31-57.
Ali K.F., Hussain E.M., Ahmed R.S., 2017. Synthesis and Characterization of New Phthalimides Containing 1, 2, 4-triazole and Imine Group. Ibn AL-Haitham Journal For Pure and Applied Science. 28(2), 86–101.
Latif M.A., Tofaz T., Chaki B.M., Tariqul Islam H.M., Hossain M., 2019. Synthesis, characterization, and biological activity of the schiff base and its Ni (II), Cu (II), and Zn (II) complexes derived from 4-(Dimethylamino) benzaldehyde and S-Benzyldithiocarbazate. Russian Journal of General Chemistry. 89(6), 1197–1201.
Hussein F.A., Ali T.E., Najim T.S., Holo K.M., 2000. Synthesis of New Derivatives of N-Substituted Saccharin via Schiff Bases. Iraqi J Chem. 26(1), 35–41.
Tomma J.H., 2010. Synthesis, Characterization and Study The Liquid Crystalline Properties of N-Acyl, Thiourea and Imidazole Derivatrives. Ibn Al-Haitham J for Pure and Appl Sci. 23(3), 134–151.
Dhahir S.S., Hussain E.M., 2020. Synthesis of Some New Schiff Bases Starting from 2, 2 Dimorpholinyl Acetic Acid and Evaluating the Biological activity. International Journal of Pharmaceutical Research. 12(1), 260-274.