Synthesis of some new aryl sulfonyl derivatives and study of their biological activity

S. Jassim Hussein, Hadeel; S. Abbas, Kareem; Abdulsaheb, Yusra S.

doi:10.22034/ecc.2023.377662.1577

Document Type : Original Research Article

Authors

¹ Department of Chemistry, College of Science, University of Misan, Maysan, 62001, Iraq

² Department of Clinical pharmacy, College of Pharmacy, University of Misan , Maysan, 62001, Iraq

https://doi.org/10.22034/ecc.2023.377662.1577

Abstract

This work focuses on the synthesis of some N-aryl sulfonyl derivatives (H₁-H₉) through the reaction of benzene sulfonyl chloride or P-toluene sulfonyl chloride with aromatic amines containing a pyrimidine ring in their structures (I-VI) in the presence of pyridine as catalyst at room temperature. The spectral data of infrared and nuclear magnetic resonance besides the C, H, N, and S analyses confirmed the validity of the synthesized derivatives. Likewise, the biological activity of the prepared derivatives (H₁ - H₉) was estimated, including antitumor and antibacterial activity. These activities were determined in vitro using the cytotoxicity assay (MTT cell viability assay) in MCF7 cells to detect the anticancer activity and Kirby-Bauer disc diffusion method used for antibiotic sensitivity test against different pathogenic strains of bacteria. In this study, the MCF-7 cell line was used to assay the anti-proliferative activity of compounds (H₁-H₉), compound H₄ was the most potent in this group with IC₅₀ value of 8.66 μg/mL and compound H₈ was the lowest in potency with IC₅₀ value of 52.29 μg/mL. In addition, the synthesized compounds have been screened for antibacterial against six multidrug resistant Gram-positive and Gram-negative bacteria and the results showed effectiveness against tested bacteria.

Graphical Abstract

Keywords

Main Subjects

Organic Chemistry

References

[1] A. Al-Mulla, A Review: Biological Importance of Heterocyclic Compounds, Der. Pharma. Chemica., 2017, 9, 141–147. [Google Scholar], [Publisher]

[2] A. Ansari, A. Ali, M. Asif, Shamsuzzaman, Review: biologically active pyrazole derivatives, New J. Chem., 2016, 41, 16–41. [Crossref], [Google Scholar], [Publisher]

[3] Y. Ju, R.S. Varma, Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives, J. Org. Chem., 2006, 71, 135–141. [Crossref], [Google Scholar], [Publisher]

[4] D. Zárate-Zárate, R. Aguilar, R.I. Hernández-Benitez, E.M. Labarrios, F. Delgado, J. Tamariz, Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products, Tetrahedron, 2015, 71, 6961–6978. [Crossref], [Google Scholar], [Publisher]

[5] E. Zarenezhad, M. Farjam, A. Iraji, Synthesis and biological activity of pyrimidines-containing hybrids: Focusing on pharmacological application, J. Mol. Struct., 2021, 1230, 129833. [Crossref], [Google Scholar], [Publisher]

[6] B. Eftekhari-Sis, M. Zirak, A. Akbari, Arylglyoxals in Synthesis of Heterocyclic Compounds, Chem. Rev., 2013, 113, 2958–3043. [Crossref], [Google Scholar], [Publisher]

[7] K. Didehban, E. Vessally, M. Salary, L. Edjlali, M. Babazadeh, Synthesis of a variety of key medicinal heterocyclic compounds via chemical fixation of CO₂ onto o-alkynylaniline derivatives, J. CO₂ Util., 2018, 23, 42–50. [Crossref], [Google Scholar], [Publisher]

[8] I.M. Lagoja, Pyrimidine as constituent of natural biologically active compounds, Chem. Biodivers., 2005, 2, 1–50. [Crossref], [Google Scholar], [Publisher]

[9] P.N. Kalaria, S.C. Karad, D.K. Raval, A review on diverse heterocyclic compounds as the privileged scaffolds in antimalarial drug discovery, Eur. J. Med. Chem., 2018, 158, 917–936. [Crossref], [Google Scholar], [Publisher]

[10] I.L. Nikonov, D.S. Kopchuk, I.S. Kovalev, G.V. Zyryanov, A.F. Khasanov, P.A. Slepukhin, V.L. Rusinov, O.N. Chupakhin, Benzyne-mediated rearrangement of 3-(2-pyridyl)-1,2,4-triazines into 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles, Tetrahedron Lett., 2013, 54, 6427–6429. [Crossref], [Google Scholar], [Publisher]

[11] D. Yadagiri, M. Rivas, V. Gevorgyan, Denitrogenative transformations of pyridotriazoles and related compounds: synthesis of N-containing heterocyclic compounds and beyond, J. Org. Chem., 2020, 85, 11030–11046. [Crossref], [Google Scholar], [Publisher]

[12] G.B. Kauffman, S.H. Chooljian, Friedrich wöhler (1800–1882), on the bicentennial of his birth, Chem. Educ., 2001, 6, 121–133. [Crossref], [Google Scholar], [Publisher]

[13] G. Guillena, D.J. Ramon, M. Yus, Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles, Chem. Rev., 2010, 110, 1611–1641. [Crossref], [Google Scholar], [Publisher]

[14] Z. Du, X. Wei, W. Zhang, Y. Zhang, Q. Xue, Catalyst-free and highly selective N,N-diallylation of anilines in aqueous phase, J. Chem., 2013, 2013, 1–6. [Crossref], [Google Scholar], [Publisher]

[15] T.A. Ramirez, B. Zhao, Y. Shi, Recent advances in transition metal-catalyzed sp³ C–H amination adjacent to double bonds and carbonyl groups, Chem. Soc. Rev., 2012, 41, 931–942. [Crossref], [Google Scholar], [Publisher]

[16] R.N. Salvatore, C.H. Yoon, K.W. Jung, Synthesis of secondary amines, Tetrahedron, 2001, 57, 7785–7812. [Google Scholar], [Publisher]

[17] M. Selva, P. Tundo, A. Perosa, Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: A convenient and selective access to mono-N-alkyl anilines, J. Org. Chem., 2001, 66, 677–680. [Crossref], [Google Scholar], [Publisher]

[18] C. Chiappe, D. Pieraccini, Direct mono-N-alkylation of amines in ionic liquids: chemoselectivity and reactivity, Green Chem., 2003, 5, 193–197. [Crossref], [Google Scholar], [Publisher]

[19] C. Feng, Y. Liu, S. Peng, Q. Shuai, G. Deng, C.-J. Li, Ruthenium-catalyzed tertiary amine formation from nitroarenes and alcohols, Org. Lett., 2010, 12, 4888–4891. [Crossref], [Google Scholar], [Publisher]

[20] K. Fujita, Y. Enoki, R. Yamaguchi, Cp∗Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines, Tetrahedron, 2008, 64, 1943–1954. [Crossref], [Google Scholar], [Publisher]

[21] S. Michlik, R. Kempe, New iridium catalysts for the efficient alkylation of anilines by alcohols under mild conditions, Chem. Eur. J., 2010, 16, 13193–13198. [Crossref], [Google Scholar], [Publisher]

[22] S.C. Yang, Y.C. Tsai, Regio- and stereoselectivity in palladium(0)-catalyzed allylation of anilines using allylic alcohols directly, Organometallics, 2001, 20, 763–770. [Crossref], [Google Scholar], [Publisher]

[23] A. Leyva-Perez, J.R. Cabrero-Antonino, A. Cantin, A. Corma, Gold(I) catalyzes the intermolecular hydroamination of alkynes with imines and produces α,α′,N-triarylbisenamines: studies on their use as intermediates in synthesis, J. Org. Chem., 2010, 75, 7769–7780. [Crossref], [Google Scholar], [Publisher]

[24] L. He, X.B. Lou, J. Ni, Y.M. Liu, Y. Cao, H.Y. He, K.N. Fan, Efficient and clean gold-catalyzed one-pot selective N-alkylation of amines with alcohols, Chem. Eur. J., 2010, 16, 13965–13969. [Crossref], [Google Scholar], [Publisher]

[25] G. Mora, B. Deschamps, S. van Zutphen, X. F. Le Goff, L. Ricard, P. Le Floch, Xanthene-phosphole ligands: synthesis, coordination chemistry, and activity in the palladium-catalyzed amine allylation, Organometallics, 2007, 26, 1846–1855. [Crossref], [Google Scholar], [Publisher]

[26] L.L. Hill, J.L. Crowell, S.L. Tutwiler, N.L. Massie, C.C. Hines, S.T. Griffin, R.D. Rogers, K.H. Shaughnessy, G.A. Grasa†, C.C.C.J. Seechurn, H. Li, T.J. Colacot, J. Chou, C.J. Woltermann, Synthesis and X-ray structure determination of highly active Pd(II), Pd(I), and Pd(0) complexes of Di(tert-butyl)neopentylphosphine (DTBNpP) in the arylation of amines and ketones, J. Org. Chem., 2010, 75, 6477–6488. [Crossref], [Google Scholar], [Publisher]

[27] Q. Zou, C. Wang, J. Smith, D. Xue, J. Xiao, Alkylation of amines with alcohols and amines by a single catalyst under mild conditions, Chem.-A Eur. J., 2015, 21, 9656–9661. [Crossref], [Google Scholar], [Publisher]

[28] M.H. Ahmed, M.A. EI-Hashash, M.I. Marzouk, A.M. EI-Naggar, Synthesis and antitumor activity of some nitrogen heterocycles bearing pyrimidine moiety, J. Heterocycl., 2020, 57, 3412-3427. [Crossref], [Google Scholar], [Publisher]

[29] A. Allahresani, M.A. Nasseri, A. Nakhaei, S. Aghajani, Co(III)@Fe₃O₄@SiO₂ salen complex as a highly selective and recoverable magnetic nanocatalyst for the oxidation of sulfides and benzylic alcohols, Eurasian Chem. Commun., 2019, 1, 153–169. [Crossref], [Google Scholar], [Publisher]

[30] M. Khalid, A. Ali, S. Haq, M.N. Tahir, J. Iqbal, A.A.C. Braga, M. Ashfaq, S.U.H. Akhtar, O-4-Acetylamino-benzenesulfonylated pyrimidine derivatives: synthesis, SC-XRD, DFT analysis and electronic behaviour investigation, J. Mol. Struct., 2021, 1224, 129308. [Crossref], [Google Scholar], [Publisher]

[31] K.R. Gari Divya, G. Lakshmi Teja, G. Yamini, A. Padmaja, V. Padmavathi, Synthesis of amido sulfonamido heteroaromatics under ultrasonication and their antimicrobial activity, Chem. Biodivers., 2019, 16, e1900291. [Crossref], [Google Scholar], [Publisher]

[32] E.J. Baron, Maturing into a diagnostic microbiologist for today, Many Faces, Many Microbes Pers. Reflections Microbiol., 2000, 107–115. [Crossref], [Google Scholar], [Publisher]

[33] R.R. Neubig, M. Spedding, T. Kenakin, A. Christopoulos, International union of pharmacology committee on receptor nomenclature and drug classification. XXXVIII. update on terms and symbols in quantitative pharmacology, Pharmacol. Rev., 2003, 55, 597–606. [Crossref], [Google Scholar], [Publisher]

[34] S.F. Barbuceanu, G. Saramet, G.L. Almajan, C. Draghici, F. Barbuceanu, G. Bancescu, New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation, Eur.J. Med. Chem., 2012, 49, 417-423. [Crossref], [Google Scholar], [Publisher]

Eurasian Chemical Communications

Synthesis of some new aryl sulfonyl derivatives and study of their biological activity

References

References

Volume 5, Issue 5
May 2023
Pages 450-465

Synthesis of some new aryl sulfonyl derivatives and study of their biological activity

References

References

Volume 5, Issue 5May 2023Pages 450-465

Volume 5, Issue 5
May 2023
Pages 450-465