Design, Synthesis, Reactions and Antibacterial Properties of 2-hydrazinyl-3-methyl-6-nitroquinoxaline Derivatives
Journal of Advances in Microbiology,
Aims: This aims of this study was to synthesis new quinoxaline-based heterocycles and study its antibacterial properties.
Objective: This study was designed to synthesis some 3-methyl-6-nitroquinoxaline-2-one with hydrazine moiety, characterize the synthesized compounds, and study their antibacterial properties on some bacterial strains.
Materials and Methods: Six 3-methylquinoxaline-2-hydrazone derivatives were synthesized by reacting 2-hydrazinyl-3-methyl-6-nitroquinoxaline with various substituted acetophenones. The hydrazones were screened for their potential antibacterial properties.
Results: All the test compounds were found to possessed promising antibacterial properties against a panel of bacterial strains screened for this study. The MIC values exhibited by these compounds ranged between 0.0313 and 0.250 mg/mL. The lowest MBC of the compounds against the test organism was 0.0625 mg/mL while the highest MBC was 0.250 mg/mL.
Discussion and Conclusion: The study concluded that all the compounds exhibited appreciable bactericidal effects against all the bacterial strains, which is an indication that such synthetic compounds possessed broad spectrum activities and such compounds could be useful in formulation of antibacterial compounds which could be used to mitigates infections caused by pathogens that are now developing resistance against the available antibiotics.
- antibacterial activity
- gram-positive bacteria
- gram-negative bacteria
- substituted acetophenone
How to Cite
Sakata G, Makino K, Kurasawa Y. Recent Progress in the Quinoxaline Chemistry. Synthesis and Biological Activity. Heterocycles. 1998;27:2481-2515.
Michael JW, Ben-Hadda T, Kchevan AT, Ramdani A, Touzani R, et al. 2,3-bifunctionalized quinoxalines: Synthesis, DNA Interactions and Evaluation of anticancer, anti-tuberculosis and anti-fungal activity. Molecules. 2002; 7:641-656.
Lindsley CW, Zhao Z, Leister WH, Robinson RG, Barnett SG, et al. Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors. Bioorganic and Medicinal Chemistry Letters. 2005;15: 761-764.
Geefhavani M, Reddy J, Sathyanarayana S. Synthesis, Antimicrobial and wound healing activiies of diphenyl quinoxaline derivatives. International Journal of Pharmacy and Technology. 2012;4:4700-4710.
Wagle S, Adhikari A, Kumari N. Synthesis of some new 2-(3-methyl7-substituted-2-oxoquinoxalinyl)-5-(aryl)-1,34-oxadiazoles as potential nonsteroidal anti-inflammatory and anagesic agents. Indian Journal of Chemistry. 2008;47:439-448.
Rajitha G, Saideepa N, Praneetha P. Synthesis and evaluation of N-(xbenzamido cinnamoyl)-aryl hydrazone derivatives for anti-inflammatory and antioxidant activities. Indian Journal of Chemistry and Biology. 2011;50:729-733.
Badran M, Abonzid K, Hussein M. Synthesis of certain substituted quinoxalines as antimicrobial agents (Part ii). Archieves of Pharmarcy Reserves. 2003;26:107-113.
Jaso A, Zarranz B, Aldana I, Monge A. Synthesis of new 2-acetyl and 2-benzoyl quinoxaline-1,4-di-N-oxide derivatives as anti-mycobacterium tuberculosis agents. European Journal of Medicinal Chemistry. 2003;39:791-800.
Hearn MJ, Cynamon MH. Design and synthesis of anti-tuberculars: preparation and evaluation against Mycobacterium tuberculosis of an isoniazid schiff base. Journal of Antimicrobial Chemotherapy. 2004;55:185-191.
Taiwo F, Akinpelu D, Obafemi C (2008) Synthesis and antibacterial activity of some quinoxaline derivatives. Ife Journal of Science 10: 19-25.
Kaurase S, Wadher N, Yeole P (2011) Microwave assisted Synthesis of hydrazone derivatives of quinoxalinone and evaluation of their antimicrobial activity. International Journal of Universal Pharmacy and Life Sciences 1: 117-126.
Aswartha UM, Sreeramulu J, Puna S. Synthesis and antimicrobial activity of a novel series of quinoxaline-2,3-dione derivatives. International Journal of Advances in Pharmaceutical Research. 2012;7:1010-1020.
Achutha L, Parameshwar R, Madhava RB, Babu H. Microwave-assisted synthesis of some quinoxaline-incoporated schiff bases and their biological evaluation. Journal of Chemistry. 2013;578438:1-5.
Chen P, Arthur MD, Derek N, Henry HG, Steven HS, et al. Imidazoquinoxaline Src-Family Kinase p56Lck Inhibitors: SAR, QSAR, and the Discovery of (S)-N-(2-Chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl) imidazo-[1,5-a]pyrido[3,2-e]pyrazin-6-amine as a Potent and Orally Active Inhibitor with Excellent in vivo. Journal of Medicinal Chemistry. 2004;47:4517-4529.
Rangisetty JB, Gupta CN, Prasad AL, Srinavas P, Sridhar N, et al. Synthesis of new arylaminoquinoxalines and their antimalaria activity in mice. Journal of Pharmacology and Pharmacy. 2001;53:1409-1413.
Bailly C, Echepare S, Gago F, Waring M. Recorgnition elements that determine affinity and sequence-specific binding DNA of 2QN a biosynthetic bis quinoline analogue of echinimycin. Anti-Cancer Drug Descriptions. 1999;15:291-303.
Burguete A, Pontiki E, Litina DH, Vicente E, Solano B. Synthesis and anti-inflammatory/antioxidant activities of some new ring substitruted 3-phenyl1-(1,4-di-N-oxide-quinoxalin-2-yl)-2-propen-1-one derivatives and their 4,5-dihydro-(1H)-pyrazole analogues. Bioorganic and Medicinal Chemistry Letters. 2007;17: 6439-6443.
Beheshtiha YS, Heravi MM, Saeedi M, Karimi N, Zakeri M, et al. Brønsted Acid Ionic Liquid [(CH2)4SO3HMIM] [HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives. Synthetic Communications. 2010;40:1216-1220.
Deepika Y, Nath PS. Design, Synthesis of Novel quinoxaline derivatives and their antinoceptive activity. Asian Journal of Pharmaceutical and Health Sciences. 2012;2:261-264.
Urquiola C, Vieites M, Aguirre G. Improving anti-trypanosomal activity of 3 aminoquinoxaline- 2-carbonitrile N1,N4-dioxide derivatives by complexation with vanadium. Bioorganic and Medicinal Chemistry, 2006l14:5503-5509.
Zarranz B, Jaso M, Lima LM. Antiplasmodial activity of 3-trifluoromethyl-2 carbonylquinoxaline di-N-oxide derivatives. Rev Bras Cienc Farm. 2006;42:55-57.
Nikam SS, Cordon JJ, Ortwine DF. Design and synthesis of novel quinoxaline 2,3-dione AMPA/GlyN receptor antagonis. Journal of Medicinal Chemistry. 1999;42:2266-2271.
Xia H, Wang F, YU K. Novel cyclophilin D inhibitors derived from quinoxaline exhibit highly inhibitory activity against rat mitochondrial swelling and Ca2+ uptake/ release. Acta Pharmacologica Sinica. 2005;26:1201-1211.
Sridevi CH, Balaji K, Naidu A. Antimicrobial Evaluation and Synthesis of Some Phenylpyrazolo benzothiazoloquinoxaline Derivatives. E-Journal of Chemistry. 2010; 7:234-238.
Dell A, William DH, Morris HR, Smith GA, Feeney J, et al. Structure revision of the antibiotic echinomycin. Journal of American Chemical Society. 1975;97: 2497-2501.
Sato S, Shiratori O, Katagiri K. The mode of action of quinoxaline antibiotics. Interaction of quinomycin a with deoxyribonucleic acid. Journal of Antibiotics. 1967;20:270-277.
Srinivas C, Sesha C, Kumar S. Efficient, convenient and reusable polyaniline sulfate salt catalyst for the synthesis of quinoxaline derivatives. Journal of Molecular Catalysis. 2007;34:227-230.
Taiwo FO, Obuotor EM, Olawuni IJ, Ikechukwu DA, Iyiola TO. Design, Synthesis and Biological Evaluation of Some Novel 3-methly quinoxaline-2-hydrazone Derivatives. Organic Chemistry Current Research. 2017;6(181):1-6.
Akinpelu DA, Kolawole DO. Phytochemical and antimicrobial activity of leave extract of Piliostigma thonniggii (Shum.). Science Focus. 20047;64-70.
Akinpelu DA, Odewade JO, Aiyegoro OA, Ashafa AOT, Akinpelu OF, Agunbiade MO. Biocidal effects of stem bark extract of Chrysophyllum albidium G. Don. On vancomycin-resistant Staphylococcus aureus. BMC Complementary and Aternative Medicine. 2016;16:105-113.
Oludare EE, Emudianugbe TS, Khaar GS, Kuteyi SA, Irobi DN. Antibacterial Properties of Leaf Extract of Cassia alata. Biology Reserves Communications. 1992; 4:1137-1142.
Odenholt I, Owdi E, Cars O. Pharmacodynamics of telithromycin in vitro against respiratory tract pathogens. Antimicrobial Agents Chemotherapy. 2001; 45:23-29.
Longbottom CJ, Carson CF, Hammer KA, Mee BJ, Riley TV. Tolerance of Pseudomonas aeruginosa to Melaleuca alternifolia (tea tree) oil is associated with the outer membrane and energy-dependent cellular processes. Journal of Antimicrobial Chemotherapy. 2004;54:386-92.
Nikaido H. Outer membrane. In: Neidhardt FC, editors. Escherichia coli and Salmonella typhimurium: Cellular and Molecular Biology.. Washington: American Society for Microbiology; 1996
Pelczar MJ, Chan EC, Kruz NR. Microbiology, 5th Edt. Teta, McGraw-Hill Publishing Company Ltd., New Delhi. 2006;119-123.
Prescott LM, Harley JP, Klein DA. Microbiology 5th Edition, McGraw-Hill Inc; 2002.
Livermore DM, Brown JD. Detection of Beta-lactmase-mediated resistance. Journal of Antimicrobial Chemotherapy. 2001;4:59-64.
Lowry FD. Staphylococcus aureus infections. New England Journal of Medicine. 1998;339(8):520-532.
Achinto S, Munirudin A. The Analgestic and anti-inflammatory activities of the extract of Albizia lebbeck in animal model. Pakistan Journal of Pharmaceutical Sciences. 2009;22:74-77.
Raccach M. The Antimicrobial Activity of Phenolic Antioxidants in Foods. Journal of Food Safety. 1984;6(3):141–170.
Blaszyk M, Holley RA. Interaction of monolaurin, eugenol and sodium citrate on growth of common meat spoilage and pathogenic organisms. International Journal of Food Microbiology. 1998;39: 175-183.
Abstract View: 44 times
PDF Download: 18 times