Preparation, Characterization, of Some Oxadiazol Derivatives Prepared from Different Carboxylic Acids
DOI:
https://doi.org/10.21123/bsj.2024.8657Keywords:
Derivatives, Drugs, Mefenamic acid, Ring-closing, Synthesis oxadiazole.Abstract
A series of Mefenamic acid derivatives were designed and synthesized and the products were characterized spectroscopically using FT-IR, 1H NMR, and 13C NMR techniques. Series A included the transformation of six drugs (Mefenamic acid, Ampiciline, Noproxen, Benzilic acid, Diclofenac acid, and cephics) which are known to have highly medicinal effectiveness to acid chloride then react with thiosemicarbazide to synthesize series B. In the third stage, oxadiazole was prepared using POCl3 as a ring-closing agent to compounds (B1-B6). The final step in the strategy was building new Mefenamic acid derivatives consisting of condensation of the Mefenamic acid chloride with the compounds (C1-C6) to give new compounds (D1-D6).
Received 30/03/2023
Revised 02/10/2024
Accepted 04/10/2024
Published Online First 20 /06/2024
References
Al-Bayati Y K, Aljabari F I. Mefenamic Acid Selective Membranes Sensor and Its Application to pharmaceutical Analysis. Baghdad Sci J 2016; 13(4): 829-837. http://dx.doi.org/10.21123/bsj.2016.13.4.0829.
Lago EM, Silva MP, Queiroz TG, Mazloum SF, Rodrigues VC, Carnaúba PU, et al. Phenotypic screening of nonsteroidal anti-inflammatory drugs identified Mefenamic acid as a drug for the treatment of schistosomiasis. EbioMedicine. 2019; 43: 370-379. https://doi.org/10.1016/j.ebiom.2019.04.029.
Amanullah A, Upadhyay A, Dhiman R, Singh S, Kumar A, Ahirwar DK, et al. Development and Challenges of Diclofenac-Based Novel Therapeutics: Targeting Cancer and Complex Diseases. Cancers. 2022; Sep 9: 14(18): 4385. https://doi.org/10.3390/cancers14184385.
Patel SS, Tripathi R, Chavda VK, Savjani JK. Anticancer potential of Mefenamic acid derivatives with platelet-derived growth factor inhibitory property. Anti-Cancer Agents in Medicinal Chemistry. Anti-Cancer Agents Med. 2020 May 1; 20(8): 998-1008. https://doi.org/10.2174/1871520620666200415100614.
Mohammed IA, Kareem, MM. Synthesis, characterization and study of some of new Mefenamic acid derivatives as cytotoxic agents. Int J Phys Conf Ser: Conf Ser. 2020; 1664(1): 012081. IOP Publishing. https://doi.org/10.1088/1742-6596/1664/1/012081.
Thiruchenthooran V, Sánchez-López E, Gliszczyńska A. Perspectives of the Application of Non-Steroidal Anti-Inflammatory Drugs in Cancer Therapy: Attempts to Overcome Their Unfavorable Side Effects. Cancers. 2023 Jan; 15(2): 475. https://doi.org/10.3390/cancers15020475.
Thiruchenthooran V, Sánchez-López E, Gliszczyńska A. Perspectives of the Application of Non-Steroidal Anti-Inflammatory Drugs in Cancer Therapy: Attempts to Overcome Their Unfavorable Side Effects. Cancers. 2023 Jan; 15(2): 475. https://doi.org/10.3390/cancers15020475.
Qassim B, Motelica-Heino M, Morabito D. Uptake of Three Pharmaceuticals by Beans (Phaseolus vulgaris L.) from Contaminated Soils. Baghdad Sci J. 2020 Sep 1; 17(3): 0733-742. http://dx.doi.org/10.21123/bsj.2020.17.3.0733.
Al-Jabari M, Khalid I, Sulaiman S, Alawi I, Shilo J. Synthesis, characterization, kinetic and thermodynamic investigation of silica nanoparticles and their application in Mefenamic acid removal from aqueous solution. Desalin. 2018 Oct 1; 129: 160-7. https://doi.org/10.5004/dwt.2018.23083.
Ayoub R, Jarrar Q, Ali D, Moshawih S, Jarrar Y, Hakim M, et al. Synthesis of novel esters of Mefenamic acid with pronounced anti-nociceptive effects and a proposed activity on GABA, opioid and glutamate receptors. Eur J Pharm Sci. 2021 Aug 1; 163: 105865. https://doi.org/10.1016/j.ejps.2021.105865Get rights and content.
Tarushi A, Geromichalos GD, Kessissoglou DP, Psomas G. Manganese coordination compounds of Mefenamic acid: In vitro screening and in silico prediction of biological activity. J Inorg. 2019 Jan 1; 190: 1-4. https://doi.org/10.1016/j.jinorgbio.2018.09.017
Smolková R, Zeleňák V, Gyepes R, Sabolová D, Imrichová N, Hudecová D, et al. Synthesis, characterization, DNA binding, topoisomerase I inhibition and antimicrobial activity of four novel zinc (II) fenamates. Polyhedron. 2018 Feb 15; 141: 230-8. https://doi.org/10.1016/j.poly.2017.11.052.
Tarushi A, Totta X, Papadopoulos A, Kljun J, Turel I, Kessissoglou DP, et al. Antioxidant activity and interaction with DNA and albumins of zinc–tolfenamato complexes. Crystal structure of [Zn (tolfenamato) 2 (2, 2′-dipyridylketoneoxime) 2]. Eur J Med Chem. 2014 Mar 3; 74: 187-98. https://doi.org/10.1016/j.ejmech.2013.12.019.
Pareek RP. Use of Mefenamic acid as a supportive treatment of COVID-19: a repurposing drug. Int J Sci Res. 2020; 9(6): 69. https://doi.org/10.21275/SR20530150407
Asadpour Behzadi S, Sheikhhosseini E, Ali Ahmadi S, Ghazanfari D, Akhgar M. Mefenamic acid as Environmentally Catalyst for Threecomponent Synthesis of Dihydropyrano [2, 3-c] Chromene and Pyrano [2, 3-d] Pyrimidine Derivatives. J Appl Chem Res. 2020 Jul 1; 14(3): 63-73. https://doi.org/20.1001.1.20083815.2020.14.3.6.2
Alkalidi RAA, Al-Tamimi EO, Al-Shammaree SAW. Synthesis and Identification of New 2-Substituted-1,3,4-Oxadiazole Compounds from Creatinine and Study Their Antioxidant Activities. J Med Chem Sci. 2023; 6(6): 1216-122. https://doi.org/10.26655/JMCHEMSCI.2023.6.2 .
uczynski M, Kudelko A. Synthesis and Biological Activity of 1, 3, 4-Oxadiazoles Used in Medicine and Agriculture. Appl Sci. 2022 Apr 8; 12(8): 3756. https://doi.org/10.3390/app12083756.
Rasheed A, Ashok Kumar CK. Tyrosine and glycine derivatives as potential prodrugs: design, synthesis, and pharmacological evaluation of amide derivatives of Mefenamic acid. J Enzyme Inhib Med Chem. 2010 Dec 1; 25(6): 804-11. https://doi.org/10.1080/87559129.2021.2014861.
Khammas SJ, Hamood AJ. Synthesis, Cytotoxicity, Xanthine Oxidase Inhibition, Antioxidant of New Pyrazolo {3, 4 d} Pyrimidine Derivatives. Baghdad Sci J. 2019 Jul 2; 16(4 Supplement): 1003-9. https://doi.org/10.21123/bsj.2019.16.4(Suppl.).1003
Amer A, El-Eraky WI, Mahgoub S. Synthesis, characterization and antimicrobial activity of some novel quinoline derivatives bearing pyrazole and pyridine moieties 14th Ibn Sina Arab py moieties Conf Heterocycl Chem Appl, 30 March-2 April 2018; 1-8. Hurgada, Egypt. https://doi.org/10.21608/ejchem.2018.3941.1345
Bousfield TW, Pearce KP, Nyamini SB, Angelis-Dimakis A, Camp JE. Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. Green Chem. 2019; 21(13): 3675-81. https://doi.org/10.1039/C9GC01180C.
Zahra U, Saeed A, Fattah TA, Flörke U, Erben MF. Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review. RSC Adv. 2022; 12(20): 12710-45 https://doi.org/10.1039/D2RA01781D.
Gandhaveeti R, Konakanchi R, Jyothi P, Bhuvanesh NS, Anandaram S. Unusual coordination mode of aroyl/acyl thiourea ligands and their π‐arene ruthenium (II) piano‐stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications. Appl Organomet. 2019 May; 33(5): e4899. https://doi.org/10.1002/aoc.4899.
Downloads
Issue
Section
License
Copyright (c) 2024 Selvana A. Yousif
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
