Research Journal of Pharmacy and Technology

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Synthesis, and Antimicrobial Evaluation of New Hydrazone Derivatives of (2,4-dinitrophenyl) Hydrazine


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1 Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad,, Iraq
     

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In this work, novel compounds of hydrazones derived from (2,4-dinitrophenyl) hydrazine were synthesized. Benzamides derivatives and sulfonamides derivatives were prepared from p-amino benzaldehyde. Then these compounds were condensed with (2,4-dinitrophenyl) hydrazine through Imine bond formation to give hydrazones compounds. The compounds were characterized using FT-IR (IR Affinity-1) spectrometer, and 1HNMR analyses. The majority of the compounds have a moderate antimicrobial activity against “Gram-positive bacteria staphylococcus Aureus, and staphylococcus epidermidis, Gram-negative bacteria Escherichia coli, and Klebsiella pneumoniae, and fungi species Candida albicans” using concentrations of 250 μg\ml.

Keywords

(2,4-dinitrophenyl) hydrazine, Schiff base, Hydrazone, Amide, Sulfonamides, Antibacterial and Antifungal activity.
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  • Lombardino JG, Lowe JA. The role of the medicinal chemist in drug discovery—then and now. Nature Reviews Drug Discovery. 2004 Oct;3(10):853-62. Doi.org/10.1038/nrd1523

  • Abbas HA, Kadry AA, Shaker GH, Goda RM. Resistance of Escherichia coli and Klebsiella pneumoniae isolated from different Sources to β-lactam Antibiotics. Research Journal of Pharmacy and Technology. 2017;10(2):589-91. Doi: 10.5958/0974-360X.2017.00116.0

  • Aljanaby AA, Aljanaby IA. Profile of antimicrobial resistance of aerobic pathogenic bacteria isolated from different clinical infections in Al-Kufa central hospital-Iraq during period from 2015 to 2017. Research Journal of Pharmacy and Technology. 2017;10(10):3264-70. Doi: 10.5958/0974-360X.2017.00579.0

  • Adusei E., Adosraku R., Oppong-Kyekyeku j. and Jibir Y. Resistance modulation action, time-kill kinetics assay, and inhibition of biofilm formation effects of plumbagin from Plumbago zeylanica Linn: Journal of Tropical Medicine, 2019. Doi: 10.1155/2019/1250645

  • Radi MF, Husain SS, Zaki AN, Sultan AA, Hamed WM, Khamis WM. Synthesis and Characterization of some new Schiff base Compounds derived from 4-Amino benzoic acid and study their biological activity. Research Journal of Pharmacy and Technology. 2019;12(5):2207-12. Doi: 10.5958/0974-360X.2019.00368.8

  • Abdulhamza HM, Farhan MS. Synthesis, Characterization and Preliminary Anti-inflammatory Evaluation of New Fenoprofen Hydrazone Derivatives. Iraqi Journal of Pharmaceutical Sciences. 2020 Dec 30;29(2):239-44. Doi.org/10.31351/vol29iss2pp239-244

  • De Oliveira Carneiro Brum J, França TC, LaPlante SR, Villar JD. Synthesis and biological activity of hydrazones and derivatives: A review. Mini-reviews in medicinal chemistry. 2020 Mar 1;20(5):342-68. Doi: 10.2174/1389557519666191014142448

  • Ali MR, Marella A, Alam MT, Naz R, Akhter M, Shaquiquzzaman M, Saha R, Tanwar O, Alam MM, Hooda J. Review of biological activities of hydrazones. Indonesian Journal of Pharmacy. 2012 Oct 1;23(4):193-202. Doi.org/10.14499/indonesianjpharm23iss4pp193-202

  • Popiolek L. Hydrazide–hydrazones as potential antimicrobial agents: overview of the literature since 2010. Medicinal Chemistry Research. 2017 Feb;26(2):287-301. Doi: org/10.1007/s00044-016-1756-y

  • Rahmani SE, Lahrech M. Evaluation of the Antioxidant Activity of some Hydrazone Schiff's bases bearing Benzotriazole Moiety. Research Journal of Pharmacy and Technology. 2018;11(9):4104-7. Doi: 10.5958/0974-360X.2018.00754.0

  • Darwish ES, Fattah AM, Attaby FA, Al-Shayea ON. Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety. International Journal of Molecular Sciences. 2014 Jan;15(1):1237-54. Doi: 10.3390/ijms15011237

  • Backes GL, Neumann DM, Jursic BS. Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides, and sulfohydrazides. Bioorganic & medicinal chemistry. 2014 Sep 1;22(17):4629-36. Doi.org/10.1016/j.bmc.2014.07.022.

  • Ade A, Amengor CD, Brobbey A, Ayensu I, Harley BK, Boakye YD. Synthesis and Antimicrobial Resistant Modulatory Activity of 2, 4-Dinitrophenylhydrazone Derivatives as Agents against Some ESKAPE Human Pathogens. Journal of Chemistry. 2020 Oct 7;2020. Doi.org/10.1155/2020/2720697.

  • Ortiz S, Nelson R, Kesternich V, Pérez-Fehrmann M, Christen P,Marcourt L. Synthesis and antifungal activity of diaryl hydrazones from 2, 4-dinitrophenylhydrazine. Journal of the Chilean Chemical Society. 2016 Sep;61(3):3081-4. Doi.org/10.4067/S0717-97072016000300015.

  • Mohsein HF, Majeed NS, Al-Ameerhelal TA. Synthesis and Characterization of some new Heterocyclic compounds containing a Sulfonamide Moiety. Research Journal of Pharmacy and Technology. 2019;12(7):3282-8. Doi: 10.5958/0974-360X.2019.00555.9

  • Bagul SD, Rajput JD, Tadavi SK, Bendre RS. Design, synthesis, and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives. Research on Chemical Intermediates. 2017 Apr;43(4):2241-52. Doi.org/10.1007/s11164-016-2759-5

  • Olfat A. Nief, Zainab Z. Mahamad, Nahida A. Jinzeel, Firyal W. Askar. Synthesis and Antimicrobial Activity of Some Sulfonamide Derivatives containing various Heterocyclic Moieties. Research J. Pharm. and Tech. 2019; 12(6):2943-2948. Doi: 10.5958/0974-360X.2019.00495.5

  • Patel KD, Patel CN, Patel GM. Synthesis and Antidiabetic Activity of Novel 4-((2, 4-Dioxothiazolidin-5-ylidene) methyl) Substituted Benzene Sulphonamide. Asian Journal of Research in Pharmaceutical Science. 2015;5(1):1-7. Doi: 10.5958/2231-5659.2015.00001.6

  • Abdul Qadir M, Ahmed M, Iqbal M. Synthesis, characterization, and antibacterial activities of novel sulfonamides derived through condensation of amino group-containing drugs, amino acids, and their analogs. BioMed research international. 2015 Feb 24;2015. Doi.org/10.1155/2015/938486

  • Igwe CN, Okoro UC. Synthesis, characterization, and evaluation for antibacterial and antifungal activities of n-heteroaryl substituted benzene sulphonamides. Organic Chemistry International. 2014 Nov 27;2014. Doi.org/10.1155/2014/419518

  • Rane YS, Varma RR, Patil LS, Athlekar SV, Chowdhary AS, Bobade AS. Synthesis and antimicrobial activity of 5-substituted-2-(1-H-benzimidazole) sulfonamides. Asian Journal of Research in Chemistry. 2010 Jun 28;3(2):335-8.

  • Bhusari KP, Amnerkar ND, Khedekar PB, Kale MK, Bhole RP. Synthesis and in vitro antimicrobial activity of some new 4-amino-N-(1, 3-benzothiazol-2-yl) benzenesulphonamide derivatives. Asian Journal of Research in Chemistry. 2008; 1(2):53-7.

  • Ojeda-Porras A, Gamba-Sánchez D. Recent developments in amide synthesis using nonactivated starting materials. The Journal of organic chemistry. 2016 Dec 2; 81(23):11548-55. Doi.org/10.1021/acs.joc.6b02358

  • Hosseyni Largani T, Imanzadeh G, Zahri S, Noroozi Pesyan N, Şahin E. A facile synthesis and antibacterial activity of novel pyrrolo [3, 4-b] quinoline-2 (3H)-yl) benzamides. Green Chemistry Letters and Reviews. 2017 Oct 2; 10(4):387-92. Doi.org/10.1080/17518253.2017.1380233

  • Lu H, Zhou X, Wang L, Jin L. Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties. Molecules. 2020 Jan;25(8):1772. Doi.org/10.3390/molecules25081772

  • Jamkhandi CM, Disouza JI. Synthesis and Antimicrobial Evaluation of 2-(1H-1, 2, 3-Benzotriazol-1-yl) N-Phenylacetamide Derivatives. Research Journal of Pharmacy and Technology. 2012; 5(8):1072-5. Doi: 10.5958/0974-360X

  • ALi H, Mohammed MH, Ismeal SH. Synthesis, Characterization, and Alpha Glucosidase Inhibition Activity of New Phthalimide Derivatives. Iraqi Journal of Pharmaceutical Sciences (P-ISSN: 1683-3597, E-ISSN: 2521-3512). 2018 Jun 5; 27(1):100-8. Doi.org/10.31351/vol27iss1pp100-108

  • 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 Chemistry. 2019; 21(13):3675-81. Doi.org/10.1039/C9GC01180C

  • Saour KY, Al-Bayati RI, Hadi MK. Synthesis of New Coumarin and 2-quinolone Derivatives with Expected Biological Activities. Iraqi Journal of Pharmaceutical Sciences. 2012; 21(2):42-50. Doi.org/10.31351/vol21iss2pp42-50

  • Sahib HA, Dakhel ZA, Hadi MK. Synthesis and Preliminary Antimicrobial Activity Evaluation of New Amide Derivatives of 2-aminobenzothiazole.IJDDT, 2021; 11(4): 1259-1261. DOI: 10.25258/ijddt.11.4.23

  • Sahib HA, Mohammed MH. Synthesis and Preliminary Biological Activity Evaluation of New N-Substituted Phthalimide Derivatives. Iraqi Journal of Pharmaceutical Sciences. 2020 Jun 25; 29(1):247-52. Doi.org/10.31351/vol29iss1pp247-252

  • Muften RA, Saour KY, Mahmood AA. Synthesis and Antimicrobial Evaluation of New 6 and7 Substituted Derivatives of Coumarin. Iraqi Journal of Pharmaceutical Sciences (P-ISSN: 1683-3597, E-ISSN: 2521-3512). 2014; 23(1):35-41. Doi.org/10.31351/vol23iss1pp35-41

  • Badal MM, Hossain MZ, Maniruzzaman M, Yousuf MA. Synthesis, identification, and computational studies of novel Schiff bases N-(2, 6-dibenzylidenecyclohexylidene)-N′-(2, 4-dinitrophenyl) hydrazine derivatives. SN Applied Sciences. 2020 Nov; 2(11):1-9. Doi.org/10.1007/s42452-020-03745-4

  • Frey J, Schneider F, Schink B, Huhn T. Synthesis of short-chain hydroxy aldehydes and their 2, 4-dinitrophenylhydrazone derivatives, and separation of their isomers by high-performance liquid chromatography. Journal of chromatography A. 2018 Jan 5; 1531:143-50. Doi.org/10.1016/j.chroma.2017.11.046


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  • Synthesis, and Antimicrobial Evaluation of New Hydrazone Derivatives of (2,4-dinitrophenyl) Hydrazine

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Authors

Halah A. Sahib
Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad,, Iraq
Mohammed K. Hadi
Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad,, Iraq
Maadh Qusay Abdulkadir
Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad, Baghdad,, Iraq

Abstract


In this work, novel compounds of hydrazones derived from (2,4-dinitrophenyl) hydrazine were synthesized. Benzamides derivatives and sulfonamides derivatives were prepared from p-amino benzaldehyde. Then these compounds were condensed with (2,4-dinitrophenyl) hydrazine through Imine bond formation to give hydrazones compounds. The compounds were characterized using FT-IR (IR Affinity-1) spectrometer, and 1HNMR analyses. The majority of the compounds have a moderate antimicrobial activity against “Gram-positive bacteria staphylococcus Aureus, and staphylococcus epidermidis, Gram-negative bacteria Escherichia coli, and Klebsiella pneumoniae, and fungi species Candida albicans” using concentrations of 250 μg\ml.

Keywords


(2,4-dinitrophenyl) hydrazine, Schiff base, Hydrazone, Amide, Sulfonamides, Antibacterial and Antifungal activity.

References