Synthesis and Investigation The Biological Activity of Some New Alkenes Based on Thiazoldin-4-one Compounds

Israa Abd Al Hassan Hamdan; J. H. Tomma

doi:10.30526/37.4.3779

Authors

Israa Abd Al Hassan Hamdan Department of Biology, College of Education For Pure Science, Al- Muthanna University, Muthanna, Iraq and Department of Chemistry, College of Education For Pure Science (Ibn Al-Haitham), University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0003-4524-5303
J. H. Tomma Department of Chemistry, College of Education For Pure Science (Ibn Al-Haitham), University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0003-4625-8341

DOI:

https://doi.org/10.30526/37.4.3779

Keywords:

Alkenes, antibacterial activity, molecular docking, Schiff bases, thiazoldin-4-ones

Abstract

This work has been done to prepare a series of new alkene compounds derived from 4-thiozolidinones by substituting different aldehydes, P-acetamido-phenol, and 2-mercapto-benzoimidazole, which were used as starting materials to form ester [I]_a,b and then make hydrazides [II]_a,b, which were used to prepare 1, 3, and 4-oxadiazoles [III]_a,b, which were then used for prepared Schiff bases [IV]_a-f, The next step was the synthesis of 4-thiazoldinone derivatives [V]_a-ffrom Schiff bases. The final step was the synthesis of alkenes [VII]_a-f, the prepared derivatives were identified with spectral methods (FT-IR, ¹H-NMR, mass, and CHNS). The antibacterial activity of the prepared derivatives was evaluated against four types of bacteria, positive gram (Staphylococcus aureus and Enterococcus faecalis.) and negative gram (E. coli and Pseudomonas aerugionsa). The final compounds gave high to moderate efficacy against Enterococcus faecalis bacteria, molecular modeling study against one of the SARS human coronavirus proteins was tested for synthesis compounds. Compound [VII]_c had a high bonding strength with the target protein, wherever it was -8.08 Kcal/mole followed by the compound [VII]_a. in the bonding strength energy, which was -7.65Kcal/mole.

References

Dhadda, S.; Sharma, S.; Jakar, P.; Sharma, H. Contemporary Progress in the Green Synthesis of Spiro-Thiazolidines and their Medicinal Significance: A Review. The Royal Society of Chemistry Advances 2023, 13(6), 3723-3742. https://pubs.rsc.org/en/content/articlepdf/2023/ra/d2ra07474e.

Irfan, A.; Batool, F.; Andleeb, S.; Naqvi, Z.; Islam, A.; Osman, S.M.; Nocentini, A.; Alissa, S.A.; Supuran, T. C. Benzothiazole Derivatives as Anticancer Agents. Journal of Enzyme Inhibition and Medicinal Chemistry 2020, 35(1), 265-279. https://doi.org/10.1080/14756366.2019.1698036.

Kumara, A.S.; Kumara, R.A.; Reddyd, E.P.; Satyanarayanaa, V.;Kashannab, J.; Reddyc, B.J.M.; Reddya, B.V.S.; Yadava, J.S. Synthesis of Novel 2-Thioxothiazolidin-4-one and Thiazolidine-2,4-dione Derivatives as Potential Anticancer Agents. Natural Product Communications 2018, 13(5), 589-559. https://doi.org/10.1177/1934578X1801300518.

Sankar, P.S.; Divya, K.; Padmaja, A.; Padmavathi, V. Synthesis and Antimicrobial Activity of Azetidinone and Thiazolidinone Derivatives from Azolylindolyl Schiff’s Bases. Journal of Medicinal Chemistry 2017, 7(11), 340-347. https://doi.org/10.4172/2161-0444.1000478.

Muhammad, A.; Raza, M.A.; Farwa, U. Synthesis, Characterization, Docking and In-Vitro evaluation of newly Synthesized Thiazolidinones. Biologia (Lahore) 2021, 67(II), 85-91. https://www.researchgate.net/publication/359699959.

Muhammad, A.; Sumrra, M.A.; Javed, S.H.; Saqib, K.; Maurin, Z.; J.K. Synthesis, Characterization and Molecular Modeling of Amino Derived Thiazolidinones as Esterase and Glucosidase Inhibitors. Journal of Molecular Structure 2020, 1219, 128609. https://doi.org/10.1016/j.molstruc.2020.128609.

Tanuja; Singh, H. Design, Synthesis, Antimicrobial and Anticancer Evaluation of Thiazole Clubbed with 4-Thiazolidinone Derivatives. Journal of Pharmaceutical Negative Results 2022, 13(9), 3400-3408. https://www.pnrjournal.com/index.php/home/article/view/4103/13087.

Kryshchyshyn-Dylevych, A.; Senkiv, J.; Roman, O.; Gzella, A.; Bielawski, K.; Bielawska, A.; Lesyk, R. Synthesis and Anticancer Activity Evaluation of 5-[2-Chloro-3-(4-nitrophenyl)-2-propenylidene]-4-thiazolidinones. Molecules 2021, 26(10), 3057. https://doi.org/10.3390 /molecul es26103057.

Chintakunta, R.; Subbareddy, G.V. Synthesis Docking Studies, Characterization and Anti-Tubercular Activity of Ofloxacin Containing Thiazolidinone Derivatives. Journal of Young Pharmacists 2022, 14(1), 77-81. https://doi.org/10.5530/jyp.2022.14.15.

Kassem, A.F.; Nassar, I.F.; Abdel-Aal, M.T.; Awad, H.M.; El-Sayed, W.A. Synthesis and Anticancer Activity of New ((Furan-2-yl)-1,3,4- Thiadiazolyl)-1,3,4-Oxadiazole Acyclic Sugar Derivatives. Chemical and Pharmaceutical Bulletine 2019, 67(8), 888–895.

https://doi.org/10.1248/cpb.c19-00280.

Kumar, B. N.;Prasanna; Mohana, K. N.; Mallesha, L. Synthesis of N-[{5-Aryl-1,3,4-oxadiazole-2-yl}methyl]-4-Methoxyaniline Derivatives and their Anticonvulsant Activity. Journal of Chemistry 2013, 121029, 1-7. https://doi.org/10.1155/2013/121029.

Gupta, V.; Pandurangan, A. Synthesis and Antimicrobial Activity of Some New 5-Oxo-Imidazolidine Derivatives. American Journal of Advanced Drug Delivery 2013, 1(4),413-421. www.ajadd.co.uk.

Yadav, S.; Narasimhan, B.; Lim, S.M.; Ramasamy, K.; Vasudevan, M.; Adnan, S.; Shah, A.; Selvaraj, M. Synthesis, Characterization, Biological Evaluation and Molecular Docking Studies of 2-(1H-Benzo[D]Imidazol-2-Ylthio)-N-(Substituted 4-Oxothiazolidin-3-Yl) Acetamides. Chemistry Central Journal 2017, 11,137. https://doi.org/10.1186/s13065-017-0361-6.

Tomma, J.H.; Al-Obaidi, O.B.; Al-Dujaili, A.H. A New Thiazoldinone and Triazole Derivatives: Synthesis, Characterization and Liquid Crystalline Properties. Journal of Molecular Structure 2022, 1270-133817. https://doi.org/10.1016/j.molstruc.2022.133817.

Tomma, J.H.; Hussein, D.H.; Jamel, N.J. Synthesis and Characterization of Some New Quinoline-2-one, Schiff bases, Pyrazole and Pyrazoline Compounds Derived from Hydrazide Containing Isoxazoline or Pyrimidine Cycles. Iraqi Journal of Science 2016, 57(2C),1316-1332.

https://www.iasj.net/iasj/issue/7262.

Tomma, J.H.; Khazaal, M.S.; Baker, R.K. Synthesis, Characterization and Antibacterial Activity of New Chalcones Derived from New Aldehyde; 4-[5-(4`Tolyl)-1,3,4-Thiadiazole-2-yl]Benzaldehyde. Ibn Al-Haitham Journal for Pure and Applied Sciences 2017, 30(3), 68-76.

https://jih.uobaghdad.edu.iq/index.ph p/j/article/view/1603/1272.

Hamdan, I.A.;Tomma, J.H. Synthesis and Study of the Biological Activity of Some New 1,3,4 Oxadiazoles Derived from Carboxylic Acid Compounds. Iraqi Journal of Science 2024, 65(4), 1800-1812. https://doi.org/10.24996/ijs.2024.65.4.2.

Illango, A.K.; Valentina, P.; Umarani, N.; Kumar, T. Synthesis and Characterization of 2,5-Disubstituted 1,3,4-Oxadiazoles as Potential Anti-Inflammatory Agents. Journal of Young Pharmacists 2009, 1(1), 72-76. https://dx.doi.org/10.4103/0975-1483.51882.

Chavan, P.S.; Nagarale, S.N.; Patil, M.V. Synthesis, Spectral Characterization and Antimicrobial Studies of New Hybrid Heterocyclic Compounds Bearing 1H-benzimidazol-2-yl Thiomethyl Motif. Indian Journal of Pharmaceutical Sciences 2017, 79(3), 385-394.

https://doi.org/10.4172/pharmaceutical-sciences.1000241.

Tandel, H.T. Synthesis and Antibacterial Activity of Coumarin Containing 4-Thiazolidinone Derivatives. Journal of Research and Analytical Reviews 2020, 7(1), 239-251. www.ijrar.org.

Alheety, K.A.; Jamell, N.M.; Tomma, J.H. Synthesis and Biological Activity of Some New Thiazolidinone Derivatives. Systemic Reviews in Pharmacy 2020, 11(3), 490-494.

https://doi.org/10.5530/srp.2020.3.62.

Hassan, H.A.; Alheety, K.A.; Hassan, D.F.; Tomma, J.H. Synthesis and Identification of Novel 2-Thioxoimidazolidin- 4-One Derivatives Containing Azo and Ester Groups. International Journal of Pharmaceutical Research 2019, 11(3), 203-209. https://doi.org/10.31838/ijpr/2019.11.03.033.

Tomma, J.H. Synthesis and Study the Mesomorphic Behaviour of Some New 1,3,4-Thiadiazoline Derivatives. Liquid Crystals 2023, 6, 998-1006. https://doi.org/10.1080/02678292. 2023.2190169.

Jamel, N.M.; Baker, R.K.; Tomma, J.H. Synthesis, Characterization and Investigation the Antibacterial Activity of New Heterocyclic Compounds Derived from 4-(4`-Methoxy Benzoyloxy) Benzaldehydethiosemicarbazone. Ibn Al-Haitham Journal for Pure and Applied Sciences 2017, 30(1), 155-168. https://jih. uobaghdad.edu.iq/index.php/j/article/view/1068/916.

Tomma, J.H.; Al-Dujaili, H.A. Mesomorphic Behaviour of Some New Schiff Base Esters Containing 1,3,4-C2H2N2O Unit. Iraqi Journal Science 2002, 43(1), 35-57.

https://doi.org/10.1088/1757-899X/1145/1/012174.

Tomma, J.H.; Abbas, S.F.; Al-Dujaili, A.H., New Quinolin-2-one, Indazole, and Benzisoxazole Derivatives Derived from Chalcones: Synthesis, Characterization, and Biological Activity. Russian Journal of Organic Chemistry 2023, 59(6), 1027–1032. https://doi.org/10.1134/S107042802306009X.

Al-Majidi, M.H.S.; Ibrahim, H.A.R.; AL-issa, Y.A.H. Synthesis and Identification of Some New Derivatives of ([Benzyl Thio) Benzimidazole-N-(Methylene-5-Yl)]-4,5-Di Substituted 1,2,4-Triazole and Evaluation of their Activity as Antimicrobial and Anti-Inflammatory Agents. Iraqi Journal of Science 2021, 62(4), 1054-1065. https://doi.org/10.24996/ijs.2021.62.4.2.

Abd-AL Hameed, W.M.; Tomma, J.H.; Baker, R.K. Synthesis and Study the Biological Activity of New Heterocyclic Compounds Derived from Hydrazide Derivatives. Indian Journal of Forensic Medicine and Toxicology 2020, 14(4),1881-1887. https://doi.org/10.37506/ijfmt.v14i4.11819.

Desai, C.N.; Jadeja, K.A.; Jadeja, D.J.; Khedkar, M.V.; Prakash, C.J. Design, Synthesis, Antimicrobial Evaluation, and Molecular Docking Study of Some 4-Thiazolidinone Derivatives Containing Pyridine and Quinazoline Moiety. Synthetic Communications 2020, 51(6), 1-12.

https://doi .org/10.1080/003979 11.2020. 1861302.

Lei, J.; Ma-Lauer, Y.; Han, Y.; Thoms, M.; Buschauer, R.; Jores, J.; Thiel, V.; Beckmann, R.; Deng, W.; Leonhardt, H.; Hilgenfeld, R.; Von Brunn, A. The SARS-Unique Domain (SUD) of SARS-Cov and SARS-Cov-2 Interacts with Human Paip1 to Enhance Viral RNA Translation. The EMBO Journal 2021, 40(11), e102277. https://doi.org/10.15252/embj.2019102277.

Staup, A.J.; De Silva, I.U.; Catt, J.T.; Tan, X.; Hammond, R.G.;Johnson, M.A. Structure of the SARS-Unique Domain C from the Bat Coronavirus HKU4. Natural Product Communications 2019, 14(5),1934578X19849202. https://doi.org/10.1177%2F1934578X19849202.

Qin, B.; Li, Z.; Tang, K.; Wang, T.; Xie, Y.; Aumonier, S.; Meitian, W.M.; Yuan, S.; Cui, S. Identification of the SARS-Unique Domain of SARS-Cov-2 as an Antiviral Target. Natural Communications 2023, 14(1), 3999. https://doi.org/10.1038/s41467-023-39709-6.