Synthesis and antimicrobial activities of some (E)-N'-1-(substituted benzylidene)benzohydrazides

  • Authors

    • V. Manikandan Department of ChemistryAnnamalai University
    • S. Balaji
    • R. Senbagam
    • R. Vijayakumar
    • M. Rajarajan
    • G. Vanangamudi
    • R. Arulkumaran
    • R. Sundararajan
    • G. Thirunarayanan
    2017-02-26
    https://doi.org/10.14419/ijac.v5i1.7155
  • (E)-N '-1-(substituted benzylidene) benzohydrazides, UV, IR and NMR spectra, Antimicrobial activities, Gram-positive and negative bacte-ria.

  • About ten substituted (E)-N'-1-(substituted benzylidene) benzohydrazides have been synthesized. They are analyzed by their analytical, ultra violet (UV), Fourier transform-IR (FT-IR) and nuclear magnetic resonance (NMR) spectral data and evaluated by antimicrobial activities such antibacterial and antifungal activities.

  • References

    1. [1] Kirilimi C, Ahmedzade M, Servi S, Koca M, Kizirgil A & Kazaz C (2008) Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2- mesitylethanone derivatives. Europian Journal of Medicinal Chemistry 43, 300–308. https://doi.org/10.1016/j.ejmech.2007.03.023.

      [2] Bourgery G, Dostert P, Lacour A, Longlois M, Pourrias M & Veaailles JT (1981) Synthesis and anti-arrhythmic activity of new benzofuran derivatives. Journal of Medicinal Chemistry 24, 159–167. https://doi.org/10.1021/jm00134a007.

      [3] Galal SA, Abd El-Al AS, Abdallah MM & El-Diwani HI (2009) Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorganic and Medicinal Chemistry Letters 19, 2420–2428. https://doi.org/10.1016/j.bmcl.2009.03.069.

      [4] Li R, Kenyon GL, Cohen FE, Chen X, Gong B, Dominguez JN, Davidson E, Kurzban G, MiLLer RE, Nuzum EO, Rosentha PJ & Mckerrow JH (1995) In vitro antimalarial activity of chalcones and their derivatives. Journal of Medicinal Chemistry 38, 5031–5037. https://doi.org/10.1021/jm00026a010.

      [5] Ballesteros JF, Sanz MJ, Ubda A, Miranda MA, Iborra S, Paya M & Alcaraz MJ (2010) Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Journal of Medicinal Chemistry 18, 1364–1370. https://doi.org/10.1016/j.bmc.2009.11.066.

      [6] Anto RJ, Sukumaran K, Kuttan J, Rao MNA, Subbaraju V & Kuttan R (1995) Anticancer and antioxidant activity of synthetic chalcones and related compounds, Cancer Letters 97, 33–40.

      [7] Mukherjee S, Kumar V, Prasad AK, Raj HG, Brakhe ME, Olsen CE, Jain SC & Parmar VP (2001) Synthetic and biological activity evaluation studies on novel 1, 3-diarylpropenones. Bioorganic and Medicinal Chemistry 9, 337–345. https://doi.org/10.1016/S0968-0896(00)00249-2.

      [8] Nielsen S F, Christensen S B, Cruciani G, Kharazmi A & Liljefors T (1998) Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis. Journal of Medicinal Chemistry 41, 4819–4832. https://doi.org/10.1021/jm980410m.

      [9] Osorio TM, Monache FD, Chiaradia ID, Mascarello A, Stumpf TR, Zanetti CR, Silveria DB, Monte Barardi CR, Albino Smania EF, Viancelli A, Totaro Garcia IA, Yunes RA, Jose Nunes R & Smania A (2012) Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus. Bioorganic and Medicinal Chemistry Letters 22, 225–230. https://doi.org/10.1016/j.bmcl.2011.11.059.

      [10] Demir H, Aeik I, Bali EB, Koc IY & Kayanak A (2009) Antioxidant and antimicrobial activities of Solidago virgaurea extracts. African Journal of Biotechnology 8, 274–279.

      [11] Ebrahimzedeh MA, Pourmarad F & Hafezi S (2008) Antioxidant activities of Iranian corn silk. Turkish Journal of Biology 32, 43–49. E-ISSN: 1303-6092. ISSN: 1300-0152

      [12] El-Sabbagh OI & Rady HM (2009) Synthesis of new acridines and hydrazones derived from cyclic beta-diketone for cytotoxic and antiviral evaluation. European Journal of Medicinal Chemistry 44, 3680–3686. https://doi.org/10.1016/j.ejmech.2009.04.001.

      [13] Raparti V, Chitre T, Bothara K, Kumar V, Dangre S, Khachane C, Gore S & Deshmane B (2009) Novel 4-(morpholin-4-yl)-N-(arylidene)benzohydrazides: Synthesis, antimycobacterial activity and QSAR investigations. European Journal of Medicinal Chemistry 44, 3954–3960. https://doi.org/10.1016/j.ejmech.2009.04.023.

      [14] Mangalam NA, Sheeja SR & Kurup MRP (2010) Mn (II) complexes of some acyl hydrazones with NNO donor sites: Synthesis, a spectroscopic view on their coordination possibilities and crystal structures. Polyhedron 29, 3318–3323. http://dx.doi.org/10.1016/j.poly.2010.09.007

      [15] Naskar S, Naskar S, Butchar RJ & Chattopadhyay SK (2010) Synthesis, X-ray crystal structures and spectroscopic properties of two Ni (II) complexes of pyridoxal Schiff’s bases with diamines: importance of steric factor in stabilization of water helices in the lattices of metal complex. Inorganica Chimica Acta 363, 404–411. https://doi.org/10.1016/j.ica.2009.11.007.

      [16] Wang Q, Pan Y, Wang J, Peng Q, Luo H & Zheng J (2011) Synthesis and biological activities of substituted N-benzoylhydrazone derivatives. African Journal of Biotechnology 10, 18013–18021. https://doi.org/10.5897/AJB10.2501.

      [17] Cukurovali A, Yilmaz B, Gur S & Kazaz C (2006) Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. European Journal of Medicinal Chemistry 41, 201–207. https://doi.org/10.1016/j.ejmech.2005.01.013.

      [18] Mamolo MG, Falagiani V, Zampieri V, Vio U, Banfi E & Scialino G (2003) Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazol-2-ylidene)hydrazide derivatives. Farmaco 58, 631–637. https://doi.org/10.1016/S0014-827X(03)00103-4.

      [19] Govindasami T, Pandey A, Palanivelu N & Pandey A (2011) Synthesis, Characterization and antibacterial activity of biologically important vanillin related hydrazone derivatives. International Journal of Organic Chemistry 1, 71–77. https://doi.org/10.4236/ijoc.2011.13012.

      [20] Dimmock JR, Vasishtha SC & Stables JP (2000) Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. European Journal of Medicinal Chemistry 35, 241–248. https://doi.org/10.1016/S0223-5234(00)00123-9.

      [21] Lima PC, Lima LM, Silva KC, Leda PH, Miranda ALP, Fraga CAM & Barreiro EJ (2000). Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. European Journal of Medicinal Chemistry 35, 187–203. https://doi.org/10.1016/S0223-5234(00)00120-3.

      [22] Salgin GU, Gokham KN, Gostal O, Koysal Y, Kilici E, Isik S, Aktay G & Ozalp M (2007) 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic anti-inflammatory and antimicrobial activities. Bioorganic and Medicinal Chemistry 15, 5738–5751. https://doi.org/10.1016/j.bmc.2007.06.006.

      [23] Silva GA, Costa LMM, Brito FCP, Miranda ALP, Barreiro EJ & Fraga CAM (2004) new class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorganic and Medicinal Chemistry 12, 3149–3158. https://doi.org/10.1016/j.bmc.2004.04.009.

      [24] Savini L, Chiasserini L, Travagli V, Pellerano C, Novellino E, Consentino S & Pisano MB (2004) New ï¡-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. European Journal of Medicinal Chemistry 39, 113–122. https://doi.org/10.1016/j.ejmech.2003.09.012.

      [25] Gaikwad ND, Patil SV & Bobade VD (2012) Hybrids of ravuconazole: synthesis and biological evaluation. European Journal of Medicinal Chemistry 54, 295–302. https://doi.org/10.1016/j.ejmech.2012.05.010.

      [26] Hassan AA, Shawky AM & Shehatta HS (2012) Chemistry and heterocyclization of thiosemicarbazones. Journal of Heterocyclic Chemistry 49, 21–37. https://doi.org/10.1002/jhet.677.

      [27] Rollas S, Gulerman N & Edeniz H (2002) Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2, 5-disubstituted-1, 3, 4-oxadiazolines. Farmaco 57, 171–174. https://doi.org/10.1002/jhet.677.

      [28] Capilla J, Serena C, Javier Pastor F, Ortoneda T & Guarro J (2003) Efficacy of voriconazole in treatment of systemic scedosporiosis in neutropenic mice. Antimicrobial Agents and Chemotherapy 47, 3976–3978. https://doi.org/10.1128/AAC.47.12.3976-3978.2003.

      [29] Abdel-Aal MT, El-Sayed WA & El-Ashry EH (2006) Synthesis and antiviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives. Archiv Der Pharmazie 339, 656–663. https://doi.org/10.1002/ardp.200600100.

      [30] Janin YL (2007) Antituberculosis drugs: ten years of research. Bioorganic and Medicinal Chemistry 15, 2479–2513. https://doi.org/10.1016/j.bmc.2007.01.030.

      [31] Bijew A (2006) new heterocyclic hydrazones in the search for antitubercular agents: Synthesis and in vitro evaluations. Letters in Drug Design and Discovery 3, 506–512. https://doi.org/10.2174/157018006778194790.

      [32] Kesel AJ (2011) Broad-spectrum antiviral activity including human immunodeficiency and hepatitis C viruses mediated by a novel retinoid thiosemicarbazone derivative. European Journal of Medicinal Chemistry 46, 1656–64. https://doi.org/10.1016/j.ejmech.2011.02.014.

      [33] Osman H, Arshad A, Kit Lam C & Bagley MC (2012) Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives. Chemistry Central Journal 6, 1–10. https://doi.org/10.1186/1752-153X-6-32.

      [34] Jaishree V, Ramdas N, Sachin J & Ramesh B (2012) In vitro antioxidant properties of new thiazole derivatives. Journal of Saudi Chemical Society 16, 371–376. https://doi.org/10.1016/j.jscs.2011.02.007.

      [35] Devasagayam TPA, De S, Adhikari S, Jain JK & Menon VP (2008) Antioxidant activity of an aminothiazole compound: possible mechanisms. Chemico-Biological Interactions 173, 215–223. https://doi.org/10.1016/j.cbi.2008.03.011.

      [36] Mor S, Mohil R, Kumar D & Ahuja M (2011) Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles. Medicinal Chemistry Research 21, 3541–3548. https://doi.org/10.1007/s00044-011-9859-y.

      [37] Rostom SAF, El-Ashmawhy MI, El-Razik HAAA, Badr MH & Ashour HMA (2009) Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents. Bioorganic and Medicinal Chemistry 17, 882–895. https://doi.org/10.1016/j.bmc.2008.11.035.

      [38] Samadhiya S & Halve A (2001) Synthetic utility of Schiff bases as potential herbicidal agents. Oriental Journal of Chemistry 17, 119–122. http://www.orientjchem.org/?p=15629

      [39] Nawrocka WP, Sztuba B, Drys A, Wietrzyk J, Ietrzyk J, Kosendiak J & Opolski A (2006) Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Part 3. Reactions of 2-arylideneaminobenzimidazole with selected 1, 3-diketones. Polish Journal of Chemistry 80, 279–287. ISSN : 0137-5083

      [40] Terzioglu N & Gursoy A (2003) Synthesis and anticancer evaluation of some new hydrazone derivatives of 2, 6-dimethylimidazo[2], [1-b][1], [3], [4]thiadiazole-5-carbohydrazide. European Journal of Medicinal Chemistry 38, 781–786. https://doi.org/10.1016/S0223-5234(03)00138-7.

      [41] Zhang HZ, Drewe J, Tseng B, Kasibhatla S & Cai SX (2004) Discovery and SAR of indole-2-carboxylic acid benzylidene-hydrazides as a new series of potent apoptosis inducers using a cell-based HTS assay. Bioorganic and Medicinal Chemistry 13, 3649–3655. https://doi.org/10.1016/j.bmc.2004.04.017.

      [42] Boga C, Fiume L, Baglioni M, Bertucci L, Farina C, Kratz F, Manerba M, Naldi M & Di Stefano (2009) Characterization of the conjugate of the (6-maleimidocaproyl)-hydrazone derivative of doxorubicin with lactosaminated human albumin by 13C NMR spectroscopy. European Journal of Pharmaceutical Sciences 38, 262–269. https://doi.org/10.1016/j.ejps.2009.08.001.

      [43] Rahman VM, Mukhtar S, Ansari WH & Lemiere G (2005) Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. European Journal of Medicinal Chemistry 40, 173–184. https://doi.org/10.1016/j.ejmech.2004.10.003.

      [44] Xia YL, Chuan-Dong F, Zhao BX, Zhao J, Shin DS & Miaom JY (2008) Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. European Journal of Medicinal Chemistry 43, 2347–2353. https://doi.org/10.1016/j.ejmech.2008.01.021.

      [45] Nerkar AG, Saxena AK, Ghone SA & Thaker AK (2009) In silico screening, synthesis and in vitro evaluation of some quinazolinone and pyridine derivatives as dihydrofolate reductase inhibitors for anticancer activity. Journal of Chemistry 6, S97–S102. https://doi.org/10.1155/2009/506576.

      [46] Vicini P, Incerti MI, Colla PL & Loddo R (2009) Anti-HIV evaluation of benzo[d]isothiazole hydrazones. European Journal of Medicinal Chemistry 44, 1801–1807. https://doi.org/10.1016/j.ejmech.2008.05.030.

      [47] Wardakhan WW, Nahed Nasser Eid ES & Mohareb RS (2013) Synthesis and antitumor evaluation of novel hydrazide and hydrazide-hydrazone derivatives. Acta Pharmaceutica 63, 45–57. https://doi.org/10.2478/acph-2013-0004.

      [48] Kaushik D, Khan SA, Chawla G & Kumar S (2010) N-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: Synthesis and anticonvulsant activity. European Journal of Medicinal Chemistry 45, 3943–3949. https://doi.org/10.1016/j.ejmech.2010.05.049.

      [49] Menendez C, Chollet A, Rodriguez F, Inard C, Pasca MR, Lherbet C & Baltas M (2012) Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents. European Journal of Medicinal Chemistry 52, 275–283. https://doi.org/10.1016/j.ejmech.2012.03.029.

      [50] Dilworth JR (1976) the coordination chemistry of substituted hydrazines. Coordination Chemistry Reviews 21, 29–62. https://doi.org/10.1016/S0010-8545(00)82050-0.

      [51] Gallego M, Garcia-Vargas M & Valcarcel M (1979) Pyridine-2-carbaldehyde 2-hydroxybenzoylhydrazone as a selective reagent for the extraction and spectrophotometric determination of iron (II). Analyst 104, 613–619. https://doi.org/10.1039/an9790400613.

      [52] Kim JS, Gatto B, Yu C, Liu A, Liu LF, La Voie EJ (1996) Substituted 2,5-Bi-1H-benzimidazoles:? Topoisomerase I inhibition and cytotoxicity. Journal of Medicinal Chemistry 39, 992–998. https://doi.org/10.1021/jm950412w.

      [53] Patil SS & Sawant AD (2001) Pyridine-2-acetaldehyde salicyloylhydrazone as reagent for extractive and spectrophoto metric determination of cobalt (II) at trace level. Indian Journal of Chemical Technology 8, 88–91.

      [54] Reddy KH & Chandrasekhar KB (2001) Simultaneous first derivative spectrophoto-metric determination of nickel (II) and copper (II) in alloys with diacetylmonoxime benzoylhydrazone. Indian Journal of Chemistry 40A, 727–732. URI: http://hdl.handle.net/123456789/18512 ISSN: 0975-0975 (Online)

      [55] Tuazon CU (1995) Other Bacillus species. In Principles and Practice of Infectious Diseases (Mandell GE, Bennett JE & Dolin R eds.), 4th edn, Churchill Livingstone, Edinburgh, pp. 1890–1894.

      [56] Rajarajan M, Senbagam R, Vijayakumar R, Manikandan V, Balaji S, Vanangamudi G & Thirunarayanan G (2015) Synthesis, spectral studies and antimicrobial activities of some substituted (E)-1-benzylidene-2-(4-bromophenyl)hydrazines. World Scientific News 3, 155–171. EISSN: 2392-2192

      [57] Kucukguzel SG, Mazi A, Sahin F, Ozturk S & Stables J (2003) Synthesis and biological activities of diflunisal hydrazide-hydrazones. European Journal of Medicinal Chemistry 38, 1005–1013. https://doi.org/10.1016/j.ejmech.2003.08.004.

      [58] Bauer AW, Kirby WMM, Sherris JC & Truck M (1966) Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology 45, 493–496. https://www.ncbi.nlm.nih.gov/pubmed/5325707

      [59] Thirunarayanan G, Vanangamudi G & Subramanian M (2012) Insect antifeedant potent substituted styryl 5-methyl-2-furyl ketones. Elixir International Journal (Organic Chemistry) 43, 6987–6989.

      [60] Aziz RK, Kansal R, Aronow BJ, Taylor WL, Rowe SL, Kubal M, Chhatwal GS, Walker MJ & Kotb M (2010) Microevolution of group A streptococci in vivo: capturing regulatory networks engaged in sociomicrobiology, niche adaptation and hypervirulence. PLoS One 5, e9798. https://doi.org/10.1371/journal.pone.0009798.

      [61] Smith KJ, Neafie R, Yeager J & Skelton HG (1999) Micrococcus folliculitis in HIV-1 disease. British Journal of Dermatology 141, 558–561. http://dx.doi.org/10.1046/j.1365-2133.1999.03060

      [62] Kluytmans J, van Belkum A & Verbrugh H (1997) Nasal carriage of Staphylococcus aureus: Epidemiology, underlying mechanisms, and associated risks. Clinical Microbiology Reviews 10, 505–520.

      [63] Perez AR, Abanes-De Mello A & Pogliano K (2000) SpoIIB localizes to active sites of septal biogenesis and spatially regulates septal thinning during engulfment in Bacillus subtilis. Journal of Bacteriology 182, 1096–1108. http://dx.doi.org/10.1128/JB.182.4 PMCID: PMC94387

      [64] Wei Y, Havasy T, McPherson DC & Popham DL (2003) Rod shape determination by the Bacillus subtilis class B penicillin-binding proteins encoded by pbpA and pbpH. Journal of Bacteriology 185, 4717–4726. http://dx.doi.org/10.1128/JB.185.16 PMID: 12896990.

      [65] Lecointre G, Rachdi L, Darlu P & Denamur E (1998) Escherichia coli molecular phylogeny using the incongruence length difference test. Molecular Biology and Evolution 15, 1685–1695. https://doi.org/10.1093/oxfordjournals.molbev.a025895.

      [66] Laboratory Methods for the Diagnosis of Vibrio cholerae. Centre for Disease Control. Retrieved 29th October 2013. https://en.wikipedia.org/wiki/Vibrio_cholerae

      [67] Brisse S, Grimont F & Grimont PAD (2006) the genus Klebsiella. In The Prokaryotes (Dworkin M, Falkow S, Rosenberg E, Schleifer KH & Stackebrandt E eds.), 3rd edn., vol. 6, Springer, New York, NY, pp. 159–196. https://doi.org/10.1007/0-387-30746-x_8.

      [68] Ohara CM, Brenner FW & Miller JM (2000) Classification, identification, and clinical significance of Proteus, Providencia, and Morganella. Clinical Microbiology Reviews 13, 534–546. https://doi.org/10.1128/CMR.13.4.534-546.2000.

      [69] Cornelis P (2000) Expressing genes in different Escherichia coli compartments. Current Opinion in Biotechnology 11, 450–454. https://doi.org/10.1016/S0958-1669(00)00131-2.

      [70] Dominguesa FC, Queiroza JA, Cabralb JMS & Fonsecab LP (2000) the influence of culture conditions on mycelial structure and cellulase production by Trichoderma reesei Rut C-30. Enzyme and Microbial Technology 26, 394–401. https://doi.org/10.1016/S0141-0229(99)00166-0.

      [71] Baron S (ed.) (1996) Medical Microbiology (Pseudomonas BHI), 4th edn, Galveston (TX): University of Texas Medical Branch at Galveston, Galveston, Texas. ISBN-10: 0-9631172-1-1

      [72] Samson R, Houbracken K, Summerbell RC, Flannigan B & Miller JD (2001) Common and important species of Actinomycetes and fungi in indoor environments. In Microorganisms in Home and Indoor Work Environments (Flannigan B, Samson R & Miller JD eds.), New York: Taylor & Francis, pp. 287−293.

      [73] Oswa S, Jukes TH, Watanabe K & Muto A (1992) Recent evidence for evolution of the genetic code. Microbiological Reviews 56, 229–264. PMCID: PMC372862

      [74] Ebbehog NE, Hansen MO, Sigsgaard T & Larsen L (2002) Building-related symptoms and molds: a two-step intervention study. Indoor Air 12, 273–277. https://doi.org/10.1016/j.sjbs.2012.06.002.

  • Downloads

  • How to Cite

    Manikandan, V., Balaji, S., Senbagam, R., Vijayakumar, R., Rajarajan, M., Vanangamudi, G., Arulkumaran, R., Sundararajan, R., & Thirunarayanan, G. (2017). Synthesis and antimicrobial activities of some (E)-N’-1-(substituted benzylidene)benzohydrazides. International Journal of Advanced Chemistry, 5(1), 17-24. https://doi.org/10.14419/ijac.v5i1.7155