Synthesis, Characterization and Antimicrobial Activity of New 4-aminoantipyrine Derivatives Using Ultrasonic Mediation
DOI:
https://doi.org/10.21123/bsj.2024.8667Keywords:
Multicomponent reaction, 1, 3-Naphthoxazine, One pot synthesis, Ultrasound irritation, Zirconyl chlorideAbstract
A straightforward, one-pot, three-component reaction between substituted aromatic aldehydes, 2-naphthol and 4- aminoantipyrine have been used to synthesis a series of new 4-(((2-hydroxynaphthalen-1-yl) (phenyl) methylene) amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one derivatives (A1- A5). This reaction was carried out with zirconyl chloride (ZrOCl2.8H2O) as an efficient catalyst under the condition of ultrasound irradiation. The fact that these derivatives have the potential to act as building blocks in the production of new compounds makes them very essential 4-(1-phenyl-1H-naphtho[1,2-e] [1,3] oxazin-2(3H)-yl)- 1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one derivatives (A6, A7 and A8). Likewise, the MCRs that resulted in the formation of hetero cyclic compound (1,3-naphthoxazine) and included 4-aminoantipyrine, formaldehyde, and 2-naphthol in a mole ratio of 1:2:1 have been employed to generate 4- (1H-naphtho [1,2-e] [1,3] oxazin-2(3H)-yl)-2-phenyl-1, 5-dimethyl-1,2-dihydro-3H-pyrazol-3-one (A9). This reaction begins with the introduction of ZrOCl2-K2CO3 catalyst system and proceeds through condensation and cyclization. All produced compounds were analyzed through IR, 1H NMR, and 13C NMR spectra data to illustrate each of these distinct structures. Using the broth microdilution and disc diffusion method, the antibacterial and anti-fungal activities of the compounds were evaluated against Gram-positive, Gram-negative, in comparison to conventional medicines (Ampicillin, Ciprofloxacin and Amoxycilline). The synthesized compounds had a wide range of action, with MIC values of 200, 600 and 1000 µg/ml against the investigated bacteria, as determined by microbiological analysis.
Received 27/02/2023
Revised 30/07/2023
Accepted 1/08/2023
Published Online First 20/02/2024
References
Ma X, Zhang W. Recent developments in one-pot stepwise synthesis (OPSS) of small molecules. Iscience. 2022. https://doi.org/10.1016 /j.isci.2022.105005
Singh RK, Dhiman A, Chaudhary S, Prasad DN, Kumar S. Current Progress in the Multicomponent CatalyticSynthesis of Amidoalkyl-Naphthols: An Update. Curr Org Chem. 2020; 24(5): 487-515. https://doi.org/10.2174/1385272822666200217100344
Bahrami S, Jamehbozorgi S, Moradi S, Ebrahimi S. Synthesis of 1‐amidoalkyl‐2‐naphthol derivatives using a magnetic nano‐Fe3O4@ SiO2@ Hexamethylenetetramine‐supported ionic liquid as a catalyst under solvent‐free conditions. J Chin Chem Soc. 2020; 67(4): 603-9. https://doi.org/10.1002/jccs.201900234
Moghanian H, Ebrahimi S. Three component, one-pot synthesis of amidoalkyl naphthols using polyphosphate ester under solvent-free conditions. J Saudi Chem Soc. 2014; 18(2): 165-8. https://doi.org/10.1016/j.jscs.2011.06.017
Li F, Zhang J, Wang L, Liu W, Yousif QA. Solvent-free synthesis of 1-amidoalkyl-2-naphthol and 3-amino-1-phenyl-1 benzo chromene-2-carbonitrile derivatives by FeO@ enamine-B (OSOH) as an efficient and novel heterogeneous magnetic nanostructure catalyst. Polish J Chem Tech. 2020; 22(2): 9-19. https://doi.org/10.2478/pjct-2020-0012
Mansoor SS, Aswin K, Logaiya K, Sudhan S. ZrOCl2• 8H2O: an efficient and recyclable catalyst for the three-component synthesis of amidoalkyl naphthols under solvent-free conditions. J Saudi Chem Soc. 2016; 20(2): 138-50. https://doi.org/10.1016/j.jscs.2012.06.003
Trammell R, Cordova A, Zhang S, Goswami S, Murata R, Siegler MA, et al. Practical One‐Pot Multistep Synthesis of 2H‐1, 3‐Benzoxazines Using Copper, Hydrogen Peroxide, and Triethylamine. European J org chem. 2021; 2021(32): 4536-40. https://doi.org/10.1002/ejoc.2021007830
Zinad DS, Mahal A, Mohapatra RK, Sarangi AK, Pratama MRF. Medicinal chemistry of oxazines as promising agents in drug discovery. Chem Biol Drug Des. 2020; 95(1): 16-47. https://doi.org/10.1111/cbdd.13633
Teran R, Guevara R, Mora J, Dobronski L, Barreiro-Costa O, Beske T, et al. Characterization of antimicrobial, antioxidant, and leishmanicidal activities of Schiff base derivatives of 4-aminoantipyrine. Molecules. 2019; 24(15): 2696. https://doi.org/10.3390/molecules241526966
Alabidi HM, Farhan AM, Al-labban HMY, Aljanaby AAJ. New derivatives from 4-amino anti-pyrine and vanillin, synthesis characterization and antibacterial activity. Egypt J Chem. 2023; 66(1): 175-81. https://doi.org/10.21608/ejchem.2022.135727.5977
Alsahib S, Baqer S, editors. Synthesis, identification of some new derivatives of 4-amino antipyrine bearing six and seven membered rings. J Phys Conf Ser.2021;.1853: 012010. https://doi.org/10.1088/1742-6596/1853/1/012010
Gaonkar SL, Nagaraj VU, Nayak S. A review on current synthetic strategies of oxazines. Mini Rev Org Chem. 2019; 16(1): 43-58. https://doi.org/10.2174/1570193X15666180531092843
Khabnadideh S, Heidari R, Amiri Zirtol L, Sakhteman A, Rezaei Z, Babaei E, et al. Efficient synthesis of 1, 3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti (IV)): anticonvulsant evaluation and computational studies. BMC chem. 2022; 16(1): 1-18. https://doi.org/10.1186/s13065-022-00836-8
Tang Z-L, Wang L, Tan J-Z, Wan Y-C, Jiao Y-C. Synthesis and Fungicidal Activity of 1-(Carbamoylmethyl)-2-aryl-3, 1-benzoxazines. Molecules. 2017; 22(7): 1103. https://doi.org/10.3390/molecules22071103
Ameen DSM. Synthesis A New Bis Oxazine and Thiazine Derivatives and Study Their Biological Activities. Al Mustansiriyah J Pharm Sci. 2022; 22(4): 56-79. https://doi.org/10.32947/ajp s.v22i4.9629
Zhang Q, Yang P, Deng Y, Zhang C, Zhu R, Gu Y. Effect of phenol on the synthesis of benzoxazine. RSC Adv. 2015; 5(125): 103203-9. https://doi.org/10.1039/C5RA17395G
Khurana I, Gupta S, Khurana JM, Rai PK. An efficient protocol for the synthesis of oxazine derivatives using a carbocatalyst in aqueous medium. Synth. Commun. 2020; 50(23): 3592-602. https://doi.org/10.1080/00397911.2020.1806327
Ibraheem IT, Araji SMA. Synthesis of New N-Substituted Phenoxazine Derivatives. Baghdad Sci J.2016; 13: 2s.https://doi.org/10.21123/bsj.2016.13.2.2NCC.0360
Sa llal ZA. Synthesis and characterization of new Oxazine, Thiazine and Pyrazol derived from chalcones. Baghdad Sci J. 2014; 11(2): 477-85. https://doi.org/10.21123/bsj.2014.11.2.477-485.
Wang T, Dai C, Qing X, Wang C. Efficient Synthesis of Substituted 2-(4 H-1, 3-benzoxazin-2-yl) Phenols via a Pseudo Three-Component Reaction. J Chem Res. 2018; 42(3): 121- 4. https://doi.org/10.3184/174751918X15199181776822.
Nguyen VT, Nguyen HT, Tran PH. One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight. New J Chem. 2021; 45(4): 2053-9. https://doi.org/10.1039/D0NJ05687A
Hamasalih RM, Mohammed KA, Khudhur PK. Contaminant Investigations of Regularly used Eye Contact Lenses. Indian J Forensic Med Toxicol . 2021; 15(2): 3264-75. https://doi.org/10.37506/ijfmt.v15i2.14871
Hamasalih RM, Abdulrahman Z. Antibiofilm potency of ginger (Zingiber officinale) and quercetin against staphylococcus aureus isolated from urinary tract catheterized patients. Appl Ecol Environ Res. 2020; 18(1): 219-36. https://dx.doi.org/10.15666/aeer/1801_219236
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