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Antimicrobial Potential of Hydrazide-Hydrazone Derivatives: a Review

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Antimicrobial Potential of Hydrazide-Hydrazone Derivatives: a Review Available online at www.ijpcr.com International Journal of Pharmaceutical and Clinical Research 2015; 7(2): 154-161 ISSN- 0975 1556 Review Article Antimicrobial Potential of Hydrazide-Hydrazone Derivatives: A Review Neeraj Kumar1*, Lalit Singh Chauhan2 1B. N. Institute of Pharmaceutical Sciences, Udaipur-313001, India 2Department of Pharmaceutical Sciences, Mohanlal Sukhadia University, Udaipur-313001 Available Online: 1st March, 2015 ABSTRACT Over the past few decades, search for newer antimicrobials remains an area of intensive investigation in the field of medicinal chemistry due to resistance developed by micro-organism to conventional antibiotics. Hydrazide-hydrazone derivatives play an important role in development of various pharmacological activities such as anticonvulsant, antimalarial, analgesic, anti-inflammatory, antiplatelet, antimicrobial, antihypertensive, antiviral, anti-tubercular, antiproliferative and antitumor activities. This review highlights antimicrobial activity shown by various hydrazide- hydrazone derivatives. Keywords: Hydrazide-hydrazone, Antimicrobial, Analgesic, Anti-inflammatory, Anticonvulsant INTRODUCTION overcome these problems, the development of new and Hydrazones possess an azometine -NHN=CH- proton that safe antimicrobial agents with better effectiveness is has found wide utility in organic synthesis.1-2 While required day by day. In this review some synthesized hydrazones have traditionally been employed as moiety for hydrazones with remarkable antimicrobial activity has the derivatization and characterization of carbonyl been discussed. compounds, in recent years the N-N linkage has been used Hydrazones of [(2-Benzothiazolylthio)acetyl]hydrazine as a key structural motif in various bioactive agents.2-4 A were synthesized and screened for antimicrobial activity number of hydrazone derivatives have been reported to against Escherichia coli, Pseudomom aeruginosa, various biological activities like anticonvulsant, Streptococcus faecalis, Staphylococcus aureus, Candida antimalarial, analgesic, anti-inflammatory, antiplatelet, albicans, Candih pseudotropicalk, Candida pmpsilosis antimicrobial, antihypertensive, antiviral, anti-tubercular, and Candida stellatoidea. All the compounds are highly antiproliferative and antitumor activities.5-22 This review potent against the yeast like fungi and bacteria tested, 1a highlights antimicrobial activity shown by various and 1b being more potent than the others against Candidu hydrazide-hydrazone derivatives. sfellatoidea.36 Antimicrobial Activity Three series of new Schiff bases and hydrazones of Antimicrobials are one of most significant weapons in substituted pyrazole were synthesized and antimicrobial fighting bacterial infections. Throughout history, there has activity of these derivatives was carried out. Among the been a continual battle between humans and the multitude synthesized compounds, compound 2a showed more of microorganisms that cause infection and disease.23-24 potent antimicrobial activity than standard.37 CDC (Centers for Disease Control) estimated that 19 A series of hydrazones of 1,2-benzisothiazole hydrazides million new infections occur each year.25-26 Bacteria and as well as their cyclic and acyclic 1,2-benzisothiazole fungi generally develop drug resistance in three ways: parent hydrazides, were synthesised and evaluated as producing metabolizing enzymes for the degradation of the antibacterial and antifungal agents. Compounds 3 and 4 drugs, modifying their targets to render the drugs proved to be the most effective against B. subtilis.38 ineffective, and expressing a high level of efflux proteins A series of new ω-nitro-1,2,4-oxadiazole-5-carbaldehyde that ‘pump’ the drug out in order to lower its hydrazones synthesized and were tested with respect to a concentration.27-30 The increasing cases of microbial series of standard microbial strains and characterized by resistance pose a major concern to the scientific minimum inhibiting concentrations. The most pronounced community and have become a threat for human life antimicrobial activity in the series of compounds studied worldwide.31-32 Moreover, invasive microbial infections with respect to the four standard microbial strains was caused by multi-drug-resistant Gram-positive bacteria and observed for compounds 5 and 6.39 microbes are difficult to diagnose and treat. They are the 4-substituted derivatives of 3-[(5-methyl-2- major cause of morbidity and mortality especially in benzoxazolinone-3-yl)methyl]-1H-1,2,4-triazole-5-(4H)- immunosuppressed and hospital-acquired patients.33-35 To thione were synthesized and screened for antimicrobial *Author for Correspondence Kumar et.al. / Antimicrobial potential of hydrazide-hydrazone… O H O N H2 R1 N S C C NH N C N R Cl S N N N C R2 S O S H N Cl HS N N Compound R1 R2 Compound 2a Compound R 1a CH3 2-OH 3 H 1b CH3 4-OCH3 4 CH3 O H N N CH R O N N N N N O N + O N N O N O -O + N O N O -O Compound 5 Compound 6 Compound R 7a H 7b CH3 7c -OCH3 O O O O F N O N+ N -O O N NH H N N H N S O O O Compound 8 Compound 9 Compound 10 O O O NH H H H2N O N O N N N O N S N S O Compound 11 Compound 12 Compound 13 activity. Most of the compounds were inactive against (N-methyl)isatin (9a and 9b, respectively) were bacteria, but they showed promising antifungal activity. It synthesized. The in vitro antimicrobial activity of all these is worth mentioning that compounds 7a, 7b, 7c showed compounds was tested against several bacteria and fungi. moderate inhibitory activities against Candida krusei, 9a and its complexes exhibited a strong inhibition of the Candida albicans and Candida parapsilosis.40 growth of Haemophilus influenzae and good antibacterial A series of hydrazide hydrazones and 1,3,4-oxadiazolines properties towards Bacillus subtilis.42 of 4-fluorobenzoic acid hydrazide synthesized and was Synthesis and antimicrobial activity of some novel tested for their antibacterial and antifungal activities hydrazide, benzochromenone, dihydropyridine, pyrrole, against Staphylococcus aureus, Escherichia coli, thiazole and thiophene derivatives have been reported. It Pseudomonas aeruginosa and Candida albicans. From was observed that compounds 10 and 11 exhibited the these compounds, 4-fluorobenzoic acid[(5-nitro-2- highest activity against S. aureus and E. coli.43 furanyl)methylene]hydrazide (8) showed equal activity Carbonyl group of methyl acetoacetate and acetylacetone with ceftriaxone against S. aureus.41 was employed to synthesize the hydrazones and screened Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of for their antimicrobial activity. Results obtained from the 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3- antibacterial activity showed that some of the syn thesized IJPCR, March 2015 - April 2015, Volume 7, Issue 2 Page 155 Kumar et.al. / Antimicrobial potential of hydrazide-hydrazone… HN N CH Ar Cl O O OH N HN N O H C Cl H 2 H R H N N H H H N HO OH N H O O Compound Ar Compound R Compound 16 14a p-BrC6H4- 15a 2,5-(CH3)2C6H3- 14b m-ClC6H4- 15b 4-CH3C6H4- 14c o-BrC6H4- 15c 4-ClC6H4- N O OH O N C NH N C R N H N NH O H N N O S O Compound R Compound 18 Compound 19 17a -H 17b -OH 17c -N(CH3)2 17d -Cl 17e -Br 17f -F 17g -CH3 17h -OCH3 O O Cl O O N O N N N N NH2 N -O N NH N+ O O O NH2 N O O O Compound 20 Compound 21 Compound 22 hydrazones i.e. hydrazones 12 and 13, may be considered Some new benzimidazole derivatives bearing hydrazone promising antibacterial agents.44 moiety were synthesized and screened them for potential Synthesis and antimicrobial activity of cholic acid antibacterial and antifungal activities. The compounds hydrazone analogues has been reported. Compounds 14a, 17b, 17d, 17e, 17g and the compounds 17a-17e, 17h were 14b and 14c indicated 15-fold stronger antimicrobial more potent than reference against P. vulgaris and P. activities against Enterobacter faecalis compared to aeruginosa, respectively.48 Cefaclor and Cefixime.45 2-Hydroxy-1-naphthaldehyde-N-methyl ethane sulfonyl Some novel chloropyrrole derivatives of aroyl hydrazones hydrazone (18) was synthesized and screened against E. and chalcones incorporating common pharmacophore of coli, P. aeruginosa, S. enterititis, S. aureus and B. cereus. pyoluteorin derivatives were synthesized and tested for The compound possesses a broad spectrum of activity antimicrobial activity. Few 1H-pyrrole-2-carbohydrazide against the tested microorganisms. It shows relatively derivatives shows activity equivalent to the standard drug better activity against Gram-negative than Gram-positive ciprofloxacin. Aroyl hydrazones 15a, 15b, and 15c were bacterias.49 found to be more active than other compounds.46 Synthesis and antimicrobial activity of a series of Synthesis and evaluation of antimicrobial activity of hydrazide-hydrzones via the reaction of cyano acetyl hydrazones derived from 3-oxido-1H-imidazole-4- hydrazine with 2-acetylfuran has been reported. carbohydrazides have been reported. Among the Compounds 2a, 6b and 7b are highly active compounds synthesized compounds, especially 16 containing non- against B. Cereus.50 substituted furan ring proved that the presence of the nitro A novel series of 2-arylquinoline-4-carboxylic acid group was essential for acquiring antibacterial activity.47 hydrazide–hydrazones was synthesized and evaluated for their in vitro antimicrobial activity against S. aureus IJPCR, March 2015 - April 2015, Volume 7, Issue 2 Page 156 Kumar et.al. / Antimicrobial potential of hydrazide-hydrazone… R 1 O2N F O O H S N S NH R2 C N N C R2 N N H N O- N O N F HN N O N+ S 2 R1 O O OH Compound R1 R2 Compound R1 R2 Compound 24a 23a 4-Cl H 24a - -OH OEt 23b 4-CH3 H 24b H -NO2 N NH H N O O N N C R1 N O O H N N NH N HN O N R N COOH O H O Compound R1 R2 Compound 27d 26a H 4F-C6H4 26d H 4OH-C6H4 26k - 4F-C6H4 CH3 26n - 4Cl-C6H4 CH3 (example for Gram-positive bacteria), Escherichia coli yl)phenylhydrazono]-3-oxobutyrate 25a was the most (example for Gram-negative bacteria) and Candida active derivative against M.
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