In vitro evaluation of novel designed, and synthesized naproxen derivatives bearing 1,2,4 triazole moiety

Sajjad. A. Hafedh; Noor H. Naser; Sahar A. Hussein

doi:10.53730/ijhs.v6nS5.10777

Authors

Sajjad. A. Hafedh Department of pharmaceutical chemistry, Faculty of Pharmacy, University of Kufa, Najaf, Iraq
Noor H. Naser Department of pharmaceutical chemistry, Faculty of Pharmacy, University of Kufa, Najaf, Iraq
Sahar A. Hussein Department of pharmaceutical chemistry, Faculty of Pharmacy, University of Kufa, Najaf, Iraq

Keywords:

naproxen, Triazole, benzoyl chloride derivatives

Abstract

The Objective of this study is created a novel derivative of the naproxen with the heterocyclic (1,2 and 4 the triazole) ring that reacted with benzoyl chloride derivatives, as well as preliminary antibacterial activity testing of the formed products. The derivatives are synthesized by esterifying naproxen hydrazine hydrate, then reacting with hydrated hydrazine and carbon disulfide, and finally reaction the benzoyl chloride derivatives (in the final step) with the triazole the derivatives of the naproxen including of amino group via a nucleophilic substitution reaction. In addition to naproxen, the antibacterial properties of the novel compounds (Va-Vd) were evaluated in agar at known doses (IN vivo). The antibacterial action of the compounds Va and Vd against staph was demonstrated in the topmost inhibited zone. In the case of E. coli, compound Vb has the smallest inhibitory zone. The findings of this study have implications to produce naproxen 1,2 and 4 the triazole-three-thiol derivatives, which reacted including the variety of benzoyl chloride derivatives. The potential of naproxen will be affected by the attraction of benzoyl chloride derivatives with para-groups on the benzen ring.

Downloads

Download data is not yet available.

References

A. A. H. S. AL-Janabi, “In Vitro Antibacterial Activity of Ibuprofen and Acetaminophen (2010),” Journal of Global Infectious Diseases, vol. 2, no. 2, pp. 105–108, doi: 10.4103/0974-777X.62880.

A. Abdel-Aziem,(2014) “Synthesis and Antimicrobial Activity of Some Novel Thiazoles, 1,3,4-Thiadiazines, 1,3,4-Thiadiazoles Incorporating Coumarin Moiety,” Journal of Heterocyclic Chemistry, vol. 52, no. 1, pp. 251–259, Dec. doi: 10.1002/jhet.2390.

A. G. Al-Bakri, G. Othman, and Y. Bustanji, (2009) “The assessment of the antibacterial and antifungal activities of aspirin, EDTA and aspirin-EDTA combination and their effectiveness as antibiofilm agents,” J. Appl. Microbiol., vol. 107, no. 1, pp. 280–286, doi: 10.1111/j.1365-2672.2009.04205.x.

A. Szczukocka-Zych, (2019) “Hypersensitivity reactions to non‐steroidal anti‐inflammatory drugs in children,” Alergologia Polska - Polish Journal of Allergology, vol. 6, no. 3, pp. 84–89, doi: 10.5114/pja.2019.88289.

A. Y. Hassan, M. T. Sarg, A. H. Bayoumi, and M. A. El-Deeb, (2018) “Synthesis and Anticancer Evaluation of Some Novel 5-Amino[1,2,4]Triazole Derivatives,” Journal of Heterocyclic Chemistry, vol. 55, no. 6, pp. 1450–1478, doi: 10.1002/jhet.3184.

Alpysbaev, K. S., Djuraev, A. M., & Tapilov, E. A. (2021). Reconstructive and restorative interventions at the proximal end of the thigh and pelvic bones in destructive pathological dislocation of the hip in children after hematogenous osteomyelitis. International Journal of Health & Medical Sciences, 4(4), 367-372. https://doi.org/10.21744/ijhms.v4n4.1779

C. K. S. Ong, P. Lirk, C. H. Tan, and R. A. Seymour, (2007) “An Evidence-Based Update on Nonsteroidal Anti-Inflammatory Drugs,” Clinical Medicine & Research, vol. 5, no. 1, pp. 19–34, doi: 10.3121/cmr.2007.698.

F. D. das Neves, (2017) “Microbiological Effectiveness of Anti-Bacterial Agents Used Inside Implants,” Journal of Dentistry & Oral Disorders, vol. 4, no. 3, Jun. doi: 10.26420/jdentoraldisord.2017.1065.

H. A. A. Ezelarab, S. H. Abbas, H. A. Hassan, and G. E.-D. A. Abuo-Rahma, (2018) “Recent updates of fluoroquinolones as antibacterial agents,” Archiv der Pharmazie, vol. 351, no. 9, p. 1800141, doi: 10.1002/ardp.201800141.

H. Karaca Gençer et al., (2017) “New Benzimidazole-1,2,4-Triazole Hybrid Compounds: Synthesis, Anticandidal Activity and Cytotoxicity Evaluation,” Molecules, vol. 22, no. 4, p. 507, doi: 10.3390/molecules22040507.

I. А. Azizovich, F. Q. Bakhtiyarovich, and I. О. Sobirovich, (2021) “Synthesis of 1,2,3-triazole derivatives based on propargyl ester of a saturated single-basic carbonic acid and para-azidobenzoic acid,” European Journal of Chemistry, vol. 12, no. 1, pp. 13–17, doi: 10.5155/eurjchem.12.1.13-17.2035.

J. Christensen, (2001) “A Simple Method for Synthesis of Active Esters of Isonicotinic and Picolinic Acids,” Molecules, vol. 6, no. 12, pp. 47–51, doi: 10.3390/60100047.

J. K. Sahu, S. Ganguly, and A. Kaushik, (2014) “Synthesis of Some Novel Heterocyclic 1,2,4-triazolo [3,4-b][1,3,4] Thiadiazole Derivatives as Possible Antimicrobial Agents,” Journal of Applied Pharmaceutical Science, pp. 811–86, doi: 10.7324/japs.2014.40214.

J. Patel, KM., Biswajit, B,. Karna, N., Patel, (2011) “Preparation and Evaluation of Sustain Release Indomethacin Tablets Using Skimmed Milk and Povidone,” Int J Curr Pharm Res, vol. 3, no. 1, pp. 7–9.

K. Schrör and B. H. Rauch, (2015) “Aspirin and lipid mediators in the cardiovascular system,” Prostaglandins & Other Lipid Mediators, vol. 121, pp. 17–23.

L. S. Simon, (1997) “Biologic effects of nonsteroidal anti-inflammatory drugs,” Current Opinion in Rheumatology, vol. 9, no. 3, pp. 178–182, doi: 10.1097/00002281-199705000-00002.

M. İ. Han and Ş. G. Küçükgüzel, (2020) “Anticancer and Antimicrobial Activities of Naproxen and Naproxen Derivatives,” Mini-Reviews in Medicinal Chemistry, vol. 20, no. 13, pp. 1300–1310, doi: 10.2174/1389557520666200505124922.

M. Zeinali et al., (2017) “Prescription pattern analysis of nonsteroidal anti-inflammatory drugs in the northeastern iranian population,” J. Res. Pharm. Pract., vol. 6, no. 4, p. 206, doi: 10.4103/jrpp.jrpp_17_45.

Mahendra a giri and rasika d bhalke, “formulation and evaluation of topical anti-inflammatory herbal gel, (2019)” Asian Journal of Pharmaceutical and Clinical Research, pp. 252–255, doi: 10.22159/ajpcr.2019.v12i7.33859.

N. Aggarwal, R. Kumar, P. Dureja, and J. M. Khurana, (2012) “ChemInform Abstract: Synthesis, Antimicrobial Evaluation and QSAR Analysis of Novel Nalidixic Acid Based 1,2,4-Triazole Derivatives.,” ChemInform, vol. 43, no. 5, p. no-no, doi: 10.1002/chin.201205176.

N. D. Rode et al., (2017) “Synthesis, biological evaluation, and molecular docking studies of novel 3-aryl-5-(alkyl-thio)-1H-1,2,4-triazoles derivatives targetingMycobacterium tuberculosis,” Chemical Biology & Drug Design, vol. 90, no. 6, pp. 1206–1214, doi: 10.1111/cbdd.13040.

N. G. Mohamed, M. M. Sheha, H. Y. Hassan, L. J. M. Abdel-Hafez, and F. A. Omar, (2018) “Synthesis, antimicrobial activity and molecular modeling study of 3-(5-amino-(2H)-1,2,4-triazol-3-yl]-naphthyridinones as potential DNA-gyrase inhibitors,” Bioorganic Chemistry, vol. 81, pp. 599–611. doi: 10.1016/j.bioorg.2018.08.031.

N. R. Appna et al., (2019) “Design and synthesis of novel 4-hydrazone functionalized/1,2,4-triazole fused pyrido[2,3-d]pyrimidine derivatives, their evaluation for antifungal activity and docking studies,” Medicinal Chemistry Research, vol. 28, no. 9, pp. 1509–1528. doi: 10.1007/s00044-019-02390-w.

Pérez, A. V., Gámez, M. R., Viteri, C. G. V., & Fernández, M. C. (2019). Renewable sources and natural disasters: A look from legal order in professional training. International Journal of Social Sciences and Humanities, 3(2), 1–9. https://doi.org/10.29332/ijssh.v3n2.283

Plech, T.; Wujec, M.; Kosikowska, U.; Malm, A.; Rajtar, B.; Polz-Dacewicz, M. (2013) Synthesis and in Vitro Activity of 1,2,4-TriazoleCiprofloxacin Hybrids against Drug-Susceptible and Drug-Resistant Bacteria. Eur. J. Med. Chem. 60, 128–1.

S. Ceylan et al., (2016) “Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton,” Heterocyclic Communications, vol. 22, no. 4. doi: 10.1515/hc-2016-0019.

S. Ramakrishna, V. Mihira, K. Raja Vyshnavi, and V. Ranjith, (2012) “Design and Evaluation of Drug Release Kinetics of Meloxicam Sustained Release Matrix Tablets,” Int. J. Curr. Pharm. Reasearch, vol. 4, no. 1, pp. 90–99.

S.-M. Li et al., (2020) “New methyl 5-(halomethyl)-1-aryl-1H-1,2,4-triazole-3-carboxylates as selective COX-2 inhibitors and anti-inflammatory agents: Design, synthesis, biological evaluation, and docking study,” Bioorganic Chemistry, vol. 104, p. 104333. doi: 10.1016/j.bioorg.2020.104333.

Suryasa, I. W., Rodríguez-Gámez, M., & Koldoris, T. (2021). Get vaccinated when it is your turn and follow the local guidelines. International Journal of Health Sciences, 5(3), x-xv. https://doi.org/10.53730/ijhs.v5n3.2938

V. Sumangala, B. Poojary, N. Chidananda, T. Arulmoli, and S. Shenoy, (2012) “Synthesis and biological evaluation of some Schiff bases of 4-amino-5-(4-methylsulfonyl)benzyl-2,4-dihydro-3H-[1,2,4]-triazole-3 thione, ” Medicinal Chemistry Research, vol. 22, no. 6, pp. 2921–2928. doi: 10.1007/s00044-012-0294-5.

Z. Hosseinzadeh and A. Ramazani, (2019) “An Overview of the Chemistry and Pharmacological Potentials of Furanones Skeletons,” Current Organic Chemistry, vol. 23, no. 14, pp. 1581–1599. doi: 10.2174/1385272823666190820111928.

Z. Peng et al., (2021) “Synthesis, antioxidant and anti-tyrosinase activity of 1,2,4-triazole hydrazones as antibrowning agents,” Food Chemistry, vol. 341, p. 128265. doi: 10.1016/j.foodchem.2020.128265.