Pharmacological aspects of hydrazides and hydrazide derivatives

Authors

  • Musa T. Abidov Institute of Immunopathology and Preventive Medicine, Ljubljana, Slovenia

DOI:

https://doi.org/10.5604/01.3001.0010.7718

Keywords:

hydrazides, hydrazone-hydrazides, isoniazid, phthalhydrazides, tamerit, galavit

Abstract

Intense search for new antimicrobials, including anti-tuberculosis drugs, is dictated by the phenomenon of bacterial multidrug resistance. Hydrazides are considered the key intermediate and valuable starting material for some novel biologically active compounds. Over 70% of recently reported synthetic hydrazide derivatives are evaluated for antimicrobial and/or antifungal activity. The most frequently applied hydrazide is an anti- tuberculosis drug isoniazid/isonicotinic acid hydrazide (NIH). Hydrazide chemicals are sharing a common functional group characterized by a nitrogen- to-nitrogen covalent bond with four substituents with at least one of them being an acyl group, whereas the related hydrazines do not carry an acyl group. Hydrazides can be further classified by atom attached to the oxygen: carbohydrazides, sulfonohydrazides, phosphonic dihydrazides, hydrazone-hydrazides and phthalhydrazides. In addition to their antibacterial and antifungal activities, hydrazide derivatives have recently attracted continuing interest because of their anti-inflammatory properties. A phthalhydrazide derivative tamerit/galavit has been successfully introduced for human therapies.

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Kumar N., Chachan L.S. Antimicrobial potential of hydrazide-hydrazonederivatives: A review. Int J Pharmaceut Clin Res, 2015, 7, 154-161.   Google Scholar

Kumari M., Narang R. Structure activity relationship and mechanism of action of hydrazide derivativesas antimicrobial molecule. J Chem Pharmaceut Res, 2016, 8, 823-836.   Google Scholar

Rollas S., Küçükgüzel S.G. Biological activities of hydrazone derivatives. Molecules, 2007, 12, 1910-1939.   Google Scholar

Kumar P., Narasimhan B. Hydrazides/hydrazones as antimicrobialand anticancer agents in the new millennium. Mini Rev Med Chem, 2013, 13, 971-987.   Google Scholar

Narang R., Narasimhan B. et al. A review on biological activities and chemical synthesis of hydrazide derivatives. Curr Med Chem, 2012, 19, 569-612.   Google Scholar

Figueiredo J.M., Camara C.A. et al. Design and synthesis of novel potentantinociceptive agents: methyl-imidazolylN-acylhydrazone derivatives. Bioorg Med Chem, 2000, 8, 2243-2248.   Google Scholar

Reddy K.K., Rao S., Rao B.S. Synthesisand characterization and biological activities of hydrazones. Int J Innovat Res Sci Engineer Technol, 2015, 4, 1844-1850.   Google Scholar

Singh N., Ranjana R., Kumari M. et al. A review on biological activities of hydrazowe derivatives. Int J Pharmaceut Clin Res, 2016, 8, 162-166.   Google Scholar

Gujan J., Awadh D. Synthesis and biological evaluation of some phenylacetic acid hydrazone derivatives. Int Res J Pharm, 2011, 2, 110-112.   Google Scholar

Abidov M.T., ed. Hapravlennaia immunokorrekcia: Problemy, perspektivy. [Directive immunocorrection: Problems and perspectives] Izdatielstvo RAMN, Moscow, 2000.   Google Scholar

Nagoev B.C., Abidov M.T., Ponezeva Z.B. Chroniczeskije virusnyje giepatity:immunopatologiczeskije, kliniko-diagnosticzeskije i terapeuticzeskije aspekty (Russian) [Chronicviral hepatitis: immunopathogenetic,clinical-diagnostic and therapeuticaspects] 2005. Guripp Adigea, Maikop.   Google Scholar

Hazari P.P., Chuttani N., Mathur R.,Sharma R. Synthesis and biological evaluation of isonicotinic acidhydrazide conjugated with diethylenetriaminepentaaceticacid for infectionimaging. Open Nucl Med J, 2009, 1, 33-42.   Google Scholar

Toliwal S., Jadav K., Patel K. Synthesis and biological evaluation of fattyhydrazides of by-products of oil processing industry. Indian J Pharmaceut Sci, 2009 (March-April), 144-148.   Google Scholar

Mohared R.M., El Sharkawy K.A.,Hussein M.M. et al. Synthesis of hydrazide-hydrazone derivatives and their evaluation of antidepressant, sedative and analgesic agents. J Pharm Sci Res, 2010, 2, 185-196.   Google Scholar

Quement S.T., Flagstad T., Mikkelsen R.J. et al. Petasis three-component coupling reactions of hydrazides for the synthesis of oxadiazolones and oxazolidinones. Org Lett, 2011, 20, 1-2.   Google Scholar

Kostecka M. Synthesis of a new group of aliphatic hydrazide derivatives and the correlations between their molecular structure and biological activity. Molecules, 2012, 17, 3560-3573.   Google Scholar

Bonacorso H.G., Paim, G.R., Porte L.M., Pittaluga E.P. et al. 6-Hydrazononicotinicacid hydrazide: a useful precursor for chemo- and regioselective synthesis of new heteroaryl-linked pridinohydrazaones. ARKIVOC, 2012, 8, 214-225.   Google Scholar

Bamanie F.H., Shehata A.S., Moustafa M.A., Mashaly M.M. Enaminones in heterocyclic syntheses: part 5: izoniazid-enaminone a new organic synthon and tuberculostatic candicate. Nat Sci, 2012, 10, 7-10.   Google Scholar

Wardakhan W.W., El-Sayed N.N., Mohareb R.M. Synthesis and anti-tumor evaluation of novel hydrazide and hydrazide-hydrazonederivatives. Acta Pharm, 2013, 63,45-57.   Google Scholar

Ivanovic I., Gligorijevic N., Arandelovic S. et al. New Ruthenium (II)-arene complexes bearing hydrazides and the corresponding (thio) semicarbazones of 3- and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. Polyhedron, 2013, 61, 112-118.   Google Scholar

Siddique M., Saeed A.B., Shahzad S.A. et al. Synthesis and biological evaluation of hydrazide based formamidesderivatives. J Sci Innovat Res, 2013, 2, 772-776.   Google Scholar

Poggi M., Barosso R., Costa-Filho A. et al. New isoniazid complexes, promising agents against Mycobacterium tuberculosis. J Mex Chem Soc, 2013, 57, 198-204.   Google Scholar

Reddy M., Reddy D., Prasad A.R. et al., Synthesis, characterization and antimicrobial activity of certain novelaryl hydrazone pyrazoline-5-onescontaining thiazole moiety. Adv Pharm Bull, 2013, 3, 153-159.   Google Scholar

El-Hashash M.A., Guirguis D.B., El-Wahed N.A. et al. Synthesis of novel series of phthalazine derivatives with antibacterial and antifungal evaluation. Chem Eng Proc Technol, 2014, 5, 1-6.   Google Scholar

Roman L., Chundak S. Synthesis, structure and characteristics of Zn(II) and Cd(II) coordination comcompounds with 3-methoxybenzene acid hydrazide and their biological activity. Chem Chemical Technol, 2014, 2, 123-128.   Google Scholar

Bhat M., Belagali S.L., Murali M. et al. Synthesis, characterization and biological activities of hydrazide Schiff’s bases. IJCPS, 2014, 3, 82-90.   Google Scholar

Reddy K.K., Rao S., Rao B.S. Synthesis and characterization and biological activities of hydrazones, 2015, 4, 18944-19850.   Google Scholar

Backes G.L., Neumann D.M., Jurisic B.S. Synthesis and antifungal activity of substituted salicyl aldehydehydrazones, hydrazides and sulfohydrazides. J Bioorg Med Chem, 2014, 22, 4629-4636.   Google Scholar

Gupta M., Kumar S., Gupta M.K. Synthesis and antimicrobial activity of some novel derivatives of 7-hydroxy-4-methyl coumarin. Int J Pharmaceut Sci, 2015, 1, 19-26.   Google Scholar

Salman A.S., Mahmoud N.A., Abdel-Aziem A. et al. Syntheis, reactions and antimicrobial activity of some new 3-substituted indole derivatives. Int J Org Chem, 2015, 5, 81-99.   Google Scholar

Kumar S., Narang R., Kumar Nayak S. et al. Synthesis, antimicrobial evaluation and QSAR studies ofN’-benzylidiene/ (1-phenylethylidiene) undec-10-enehydrazides. J Appl Pharm Sci, 2016, 6, 104-116.   Google Scholar

Sangani C.B., Makwana J.A., et al. Synthesis of 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity. Res Chem Intermed, 2016, 42, 2101-2117.   Google Scholar

Rollas S., Küçükgüzel S.G. Biological activities of hydrazone derivatives. Molecules, 2007, 12, 1910-1939.   Google Scholar

Kumar P., Narasimhan B. Hydrazides/hydrazones as antimicrobial and anticancer agents in the new millennium. Mini Rev Med Chem, 2013, 13, 971-987.   Google Scholar

Narang R., Narasimhan B. et al. A review on biological activities and chemical synthesis of hydrazide derivatives. Curr Med Chem, 2012, 19, 569-612.   Google Scholar

Figueiredo J.M., Camara C.A. et al. Design and synthesis of novel potentantinociceptive agents: methyl-imidazolylN-acylhydrazone derivatives Bioorg Med Chem, 2000, 8, 2243-2248.   Google Scholar

Koopaei M.N., Assarzadeh J. et al. Synthesis and analgesic activity of novel hydrazide and hydrazine derivatives. Iranian J Pharm Res, 2013, 12, 721-727.   Google Scholar

Cordeiro N.M., Freitas R.H., Fraga C.A. et al. Discovery of novel orallyactive tetrahydro-naphthyl-N-acylhydrazoneswith in vivo anti-TNF-αeffect and remarkable anti-inflammatoryproperties. PLOS One, 2016, 10, 1-17.   Google Scholar

Ghahremandzadeh R., Ahadi S. et al. Reaction of phtahlhydrazide and acetylendedicarboxylates in the presence of N-heterocycles: an efficient synthesis of phthalhydrazidederivatives. Tetrahydron Lett, 2008, 49, 4479-4482.   Google Scholar

Gupta P., Gupta J.K. et al. Synthesisand biological significance of pyrazolonens: A review. Int J Pharm Sci Res, 2015, 6, 2291-2310.   Google Scholar

Sangani C.B., Makwana J.A. et al. Synthesis of 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity. Res Chem Intermed, 2016, 42, 2101-2117.   Google Scholar

Timmins G.S., Deretic V. Mechanisms of action of isoniazid. Mol Microbiol, 2006, 62, 1220-1227.   Google Scholar

Getahun H., Granich R., Sculier D. et al. Implementation of isoniazid preventive therapy for people living with HIV worldwide: barriers andsolutions. AIDS, 2010, 24(5), 57-65.   Google Scholar

Kozminykh V.O. Synthesis and biological activity of substituted amidesand hydrazides of 1,4-dicarboxylicacids (A review). Pharm Chem J, 2006, 40, 8-15.   Google Scholar

Saukkonen J.J., Cohn D.L., Jasmer R.M. et al. An official ATS statement: Hepatotoxicity of antituberculosis therapy. Am J Respir Crit Care Med, 2006, 174, 935-952.   Google Scholar

Zeiger E., Anderson B., Haworth S., Lawlor T., Mortelmans K. Salmonellamutagenicity tests: V. Results from the testing of 311 chemicals. Environ Mol Mutagen, 1992, 19, 2-141.   Google Scholar

Dao T.V., Casas A.I., Maghzal G.J. et al. Pharmacology and clinical drugcandidates in redox medicine. Antiox Redox Signal, 2015, 23, 1113-1125.   Google Scholar

Narang R., Sharma S., Narasimhan B. Evaluation of anti-inflammatory activity of acid hydrazide derivatives. Hygeia J Drug Med, 2012, 4, 15-20.   Google Scholar

Shekharchi M., Navidpour L., Khorami A.R. et al. Synthesis of N-aryldiene-2-(-2-phenoxyphenyl) acetohydrazidesas anti-inflammatory agents. Iranian J Pharmacol Res, 2011, 10, 369-377.   Google Scholar

Melo T.R., Cheluci R.C., Pires M.L. et al. Pharmacological evaluation and preparation of nonsteroidal ananti-inflammatory drugs containing N-acyl hydrazone derivative. Int J Mol Sci, 2014, 15, 5821-5837.   Google Scholar

Lacerda R.B., Sales N.M., Silva L.L. et al. Novel potent inidazo [1,2-a] pyridine-N-glicinyl- hydrazone inhibitors of TNF-α production: in vitro and in vivo studies. PLOS ONE, 2014, 9, e91660.   Google Scholar

Patel U., Rajasingh S., Samanta S. et al. Macrophage polarization in response to epigenetic modifiers during infection and inflammation. Drug Discov Today, 2016, 22, 186-193.   Google Scholar

Shao J., Li Y., Wang Z., Xiao M et al. 7b, a novel naphthalimide derivative, exhibited anti-inflammatoryeffects via targeted-inhibiting TAK1following down-regulation ERK1/2-and p38 MAPK-mediated activation of NF-κB in LPS stimulated RAW264.7 macrophages. Int Immunopharmacol, 2013, 17, 216-228.   Google Scholar

Schultze J.L. Reprogramming macrophages – new opportunities for therapeutic targeting. Curr Opin Pharmacol, 2016, 26, 10-15.   Google Scholar

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Published

2017-06-30

How to Cite

Abidov, M. (2017). Pharmacological aspects of hydrazides and hydrazide derivatives. Health Promotion & Physical Activity, 2(3), 9–24. https://doi.org/10.5604/01.3001.0010.7718

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