Synthesis and Characterization of Some New Pyrazole, Triazole, Oxadiazole, Thiazole, Thiadiazole Derivatives Bearing p-Toluenesulfonamide

Authors

  • Maha A. Al-Hamad Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq.
  • Ammar H. Al-Sabawi Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq. https://orcid.org/0000-0002-8991-2991

DOI:

https://doi.org/10.21123/bsj.2024.8533

Keywords:

Benzene sulfonamide, Oxadizole, pyrazole, Thiazole, Triazole.

Abstract

A series of new heterocyclic derivatives A5-A15 have been synthesized using 4-(toluene-4-sulfinylamino)-benzoic acid ethyl ester A2 as a predecessor. This compound A2 was successfully used in synthesis of some new derivatives of oxadiazole, pyrazole, triazole, thiadiazole, thiazole and fused heterocyclic containing         p-toluene sulfonamide moiety that supposed to have important biological activities. 1H-NMR, 13C-NMR and FT-IR spectroscopy were used to confirm the prepared compounds.

References

Popiołek Ł, Tuszyńska K, Biernasiuk A. Searching for novel antimicrobial agents among hydrazide-hydrazones of 4-iodosalicylic acid. Biomed. Pharmacother. 2022; 153: 113302. https://doi.org/10.1016/j.biopha.2022.113302.

Nasr T, Bondock S, Rashed M, Fayad W, Youns M, Sakr T M. Novel hydrazide-hydrazone and amide substituted coumarin derivatives: Synthesis, cytotoxicity screening, microarray, radiolabeling and in vivo pharmacokinetic studies. Eur J Med Chem. 2018; 151: 723-739. https://doi.org/10.1016/j.ejmech.2018.04.014.

Thorat BR, Mali SN, Rani D, Yamgar RS. Synthesis, In silico and In vitro Analysis of Hydrazones as Potential Antituberculosis Agent. Curr Comput Aided Drug Des. 2021; 17(2): 294-306. https://doi.org/10.2174/1573409916666200302120942.

Azzam RA, Elboshi HA, Elgemeie GH. Novel Synthesis and Antiviral Evaluation of New BenzothiazoleBearing N Sulfonamide 2 Pyridone Derivatives as USP7 Enzyme Inhibitors. ACS Omega. 2020; 5: 30023−30036. https://doi.org/10.1021/acsomega.0c04424.

Abdollahi O, Mahboubi A, Hajimahdi Z, Zargh A. Design, Synthesis, Docking Study, and Biological Evaluation of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide Derivatives as Anti-HIV-1 and Antibacterial Agents. Iran J Pharm Res. 2022; 21(1): 1-11. https://doi.org/10.5812/ijpr-126562.

Alsayari A, Bin Muhsinah A, Asiri Y, Al-Aizari F, Kheder N, Almarhoon Z, et al. Synthesis, Characterization, and Biological Evaluation of Some Novel Pyrazolo[5,1- b]thiazole Derivatives as Potential Antimicrobial and Anticancer Agents. Molecules. 2021; 26(17): 5383. https://doi.org/10.3390/molecules26175383

Ramírez H, Fernandez E, Rodrigues J, Mayora S, Martínez G, Celis C, et al. Synthesis and antimalarial and anticancer evaluation of 7-chlorquinoline-4-thiazoleacetic derivatives containing aryl hydrazide moieties. Arch Pharm. 2021; 354(7): 1-11. https://doi.org/10.1002/ardp.202100002.

Gera A, Mohan C, Madan J, Arora S. Molecular Hybrids of N-Phthaloylglycyl Hydrazide and Hydrazinecarbothioamide with Anti-inflammatory and Anti-oxidant Activities. Curr Org Synth. 2019; 16(7): 1055-1066. https://doi.org/10.2174/1570179416666190306141318.

Chandrasekhar M, Prasad G, Venkataramaiah C, Naga Raju C, Seshaiah K, et al. Synthesis, spectral characterization, docking studies and biological activity of urea, thiourea, sulfonamide and carbamate derivatives of imatinib intermediate. Mol Divers. 2019 ; 23(3): 723-738. https://doi.org/10.1007/s11030-018-9906-4.

Yan X, Chen S, Sun W, Zhou X, Yang D, Yuan H, et al. Primary Mode of Action of the Novel Sulfonamide Fungicide against Botrytis cinerea and Field Control Effect on Tomato Gray Mold. Int J Mol Sci. 2022 ;23(3): 1526. https://doi.org/10.3390/ijms23031526.

Droctové L, Lancien M, Tran V, Susset M, Jego B, Theodoro F, Kessler P, Mourier G, Robin P, Siramakan Diarra S, Palea S, Flahault A, Chorfa A, Corbani M, Llorens-Cortes C, Mouillac B, Mendre C, Pruvost A, Servent D, Truillet C, Gilles N. A snake toxin as a theranostic agent for the type 2 vasopressin receptor. Theranostics. 2020 ;10(25): 11580-11594. https://doi.org/10.7150/thno.47485.

Vullo D, De Luca V, Scozzafava A, Carginale V, Rossi M, Supuran, C. T, et al.The extremo-α-carbonic anhydrase from the thermophilic bacterium Sulfurihydrogenibium azorense is highly inhibited by sulfonamides. Bioorg Med Chem. 2013; 21(15): 4521-4525. https://doi.org/10.1016/j.bmc.2013.05.042.

Natarajan A, Guo Y, Harbinski F, Fan Y-H, Chen H, Luus, et al. Novel arylsulfoanilide− oxindole hybrid as an anticancer agent that inhibits translation initiation. J Med Chem. 2004; 47(21): 4979-4982. https://doi.org/10.1021/jm0496234.

Levin J, Chen J, Du M, Nelson F, Killar L, Skala S, et al. Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1′ group. Bioorg Med Chem Lett. 2002; 12(8): 1199-1202. https://doi.org/10.1016/s0960-894x(02)00136-1.

Al-Sanea M, Hamdi A, Brogi S, Tawfik S, Othman D, Elshal M, et al. Design, synthesis, and biological investigation of oxadiazolyl, thiadiazolyl, and pyrimidinyl linked antipyrine derivatives as potential non-acidic anti-inflammatory agents. J Enzyme Inhib Med Chem. 2023 ; 38(1): 2162511. https://doi.org/10.1080/14756366.2022.2162511.

Telehoiu A, Nuță D, Căproiu M, Dumitrascu F, Zarafu I, Ioniță P, et al, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9 H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds. Molecules. 2020; 25(2): 1-18. https://doi.org/10.3390/molecules25020266.

Albratty M, El-Sharkawy K A, Alhazmi H A. Synthesis and evaluation of some new 1,3,4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents. Acta Pharm. 2019; 69(2): 261–276. https://doi.org/10.2478/acph-2019-0015.

Lelyukh M, Martynets M, Kalytovska M, Drapak I, Harkov S, Chaban T, Matiychuk V. Approaches for synthesis and chemical modification of non-condensed heterocyclic systems based on 1,3,4-oxadiazole ring and their biological activity: A review. J Appl Pharm Sci. 2020; 10 (10): 151–165. http://dx.doi.org/10.7324/JAPS.2020.1010016.

Ahsan M, Choupra A, Sharma R, Jadav S, Padmaja P, Hassan Z, et al. Rationale Design, Synthesis, Cytotoxicity Evaluation, and Molecular Docking Studies of 1,3,4-oxadiazole Analogues. Anticancer Agents Med Chem. 2018; 18(1): 121–138. https://doi.org/10.2174/1871520617666170419124702.

Al-Zubiady S, Al-Khafaji Z, Mohamed I, Adday S. Synthesis, Characterization and Biological Activates Studies of some New Derivatives From 2-aminoo-5-mercapto-1,3,4-thiadiazole. Baghdad Sci J. 2018; 15(1): 48-56. http://dx.doi.org/10.21123/bsj.2018.15.1.0048.

Serban G, Stanasel O, Serban E, Bota S. 2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents. Drug Des Devel Ther. 2018; 18 (12): 1545–1566. https://doi.org/10.2147/DDDT.S155958.

Farooqi S.I, Arshad N, Channar P A, Perveen F, Saeed A, Larik F A, Javeed A. Synthesis, theoretical, spectroscopic and electrochemical DNA binding investigations of 1, 3, 4-thiadiazole derivatives of ibuprofen and ciprofloxacin: Cancer cell line studies. J Photochem Photobiol B. 2018; 189: 104–118. https://doi.org/10.1016/j.jphotobiol.2018.10.006.

Serban G. Future prospects in the treatment of parasitic diseases: 2-amino-1,3,4-thiadiazoles in leishmaniasis. Molecules 2019; 24 (8) :1557. https://doi.org/10.3390/molecules24081557.

Kumari1 M, Tahlan S, Narasimhan B, Ramasamy K, Lim S, Shah S, et al. Synthesis and biological evaluation of heterocyclic 1,2,4‑triazole scaffolds as promising pharmacological agents. BMC Chem. 2021; 15(1): 1-16. https://doi.org/10.1186/s13065-020-00717-y.

Abdulameer J, Alias M. Heavy Metal Complexes of 1, 2, 3-Triazole derivative: Synthesis, Characterization, and Cytotoxicity Appraisal Against Breast Cancer Cell Lines (MDA-MB-231). Baghdad Sci J. 2022, 19(6): 1410-1422. https://dx.doi.org/10.21123/bsj.2022.7178.

Munir1 R, Zia-ur-Rehman M, Athar M, Javid N, Roohi A, Razavi S. Novel Quinolinyl – Sulphonamide Hybrid Schiff Bases as Potent Radical Scavengers to Combat Oxidative Stress. Pak J Zool. 2020; 53(1): 87-92. https://dx.doi.org/10.17582/journal.pjz/20190620180646.

Al-Hamad M A, Al-Sabawi A H. Synthesis and Characterization of Some New 4-Methyl-N-{4-[6-(substituted aryl)- [1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]-phenyl}-benzenesulfonamides. Indian J Heterocycl Chem. 2023; 33(1): 109-113. https://doi.org/10.59467/IJHC.2023.33.109.

Hassan R A, Al-Sabawi A H. Synthesis of Some New α, β-Unsaturated Carbonyl Compounds, Thiophene, Imine and Coumarin Derivatives Containing Hydrazide-Hydrazone Moiety. Egypt J Chem. 2023; 66(6): 383 – 391. https://doi.org/10.21608/ejchem.2022.156323.6764.

Sharma V, Kumar R, Angeli A, Supuran C T, Sharma P K. Tail approach synthesis of novel benzenesulfonamides incorporating 1, 3, 4-oxadiazole hybrids as potent inhibitor of carbonic anhydrase I, II, IX, and XII isoenzymes. Eur J Med Chem. 2020; 193: 112219. https://doi.org/10.1016/j.ejmech.2020.112219.

Glukhacheva V, Sergey G, Kazantsev I, Shestakova E, Dmitri S, Eltsov I, et al. New Reaction Products of Acetylacetone with Semicarbazide Derivatives. ACS Omega. 2021; 6: 8637−8645. https://doi.org/10.1021/acsomega.1c00518.

A Othman M, M Daoud K. Synthesis and Study of Some 4-Chlorophenoxy Methyl Substituted amido1, 3, 4-Oxadiazoles, 1, 3, 4-Thiadiazoles and 1, 2, 4-Triazoles from 4-Chloro phenoxy acetic acid. J Edu Sci. 2013; 26(4): 47-55. http://dx.doi.org/10.33899/edusj.2013.89978.

Shainova R, Gomktsyan T, Karapetyan A, Yengoyan A. Synthesis and biological evaluation of 3-O-substituted 1-benzyl-6-oxo-1,6-dihydropyridazine derivatives. J Chem Res. 2019; 43(9-10): 352–358. https://doi.org/10.1177/1747519819866402.

Othman M A. Synthesis and Study of Some fused Substituted 1, 3, 4-Thiadiazoles and 1, 2, 4-Triazoles from 4-Chloro-phenoxy acetic acid and 2, 4-dichlorophenoxy acetic acid. J Edu Sci. 2020; 29(3): 218-226. http://dx.doi.org/10.33899/edusj.2020.166251.

Al-Iraqi M, Al-Allaf H. Synthesis of Some 2-Substituted Quinazolin-4(3H)-one Compounds from Methyl α-[(4-oxoquinazolin-2-yl)thio]acetate. Egypt J Chem. 2021; 64(12): 7263–7270. https://doi.org/10.21608/EJCHEM.2021.78538.3844

Downloads

Issue

Section

article

How to Cite

1.
Synthesis and Characterization of Some New Pyrazole, Triazole, Oxadiazole, Thiazole, Thiadiazole Derivatives Bearing p-Toluenesulfonamide. Baghdad Sci.J [Internet]. [cited 2024 Apr. 30];21(10). Available from: https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/8533