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Antimicrobial evaluation of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides and QSAR studies

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Abstract

A series of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides (1–20) was synthesized and tested for in vitro antimicrobial activity against S. aureus, B. subtilis, E. coli, C. albicans and A. niger. The results of antimicrobial studies indicated that 3-phenylacrylic acid-(3-hydroxybenzylidene)-hydrazide, 16, was the most effective as it showed both bactericidal and fungicidal properties and other compounds possessed bacteriostatic/fungistatic activity. The multi-target QSAR model demonstrated that the topological parameter, Balaban topological index (J) is effective in describing the antimicrobial activity of synthesized substituted hydrazides.

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References

  • Al-Mawsawi LQ, Dayam R, Taheri L, Witvrouw M, Debyser Z, Neamati N (2007) Discovery of novel non-cytotoxic salicylhydrazide containing HIV-1 integrase inhibitors. Bioorg Med Chem Lett 17:6472–6475

    Article  PubMed  CAS  Google Scholar 

  • Bajaj S, Sambi SS, Madan AK (2005) Prediction of anti-inflammatory activity of N-arylanthranilic acids: computational approach using refined Zagreb Indices. Croat Chem Acta 78(2):165–174

    CAS  Google Scholar 

  • Balaban AT (1982) Highly discriminating distance-based topological index. Chem Phys Lett 89:399–404

    Article  CAS  Google Scholar 

  • Cappucino JG, Sherman N (1999) Microbiology—a laboratory mannual. Addison Wesley Longman Inc, California, p 263

    Google Scholar 

  • Cruz-Monteagudo M, Gonzalez-Diaz H, Aguero-Chapin G, Santana L, Borges F, Dominguez ER, Podda G, Uriarte E (2007) Computational chemistry development of a unified free energy Markov model for the distribution of 1300 chemicals to 38 different environmental or biological systems. J Comput Chem 28(11):1909–1923

    Article  PubMed  CAS  Google Scholar 

  • Emami S, Foroumadi A, Falahati M, Loffali E, Rajabalian S, Ebrahimi SA, Farahyar S, Shafiee A (2008) 2-Hydroxy phenacyl azoles and related azolium derivative as antifungal agents. Bioorg Med Chem Lett 18:141–146

    Article  PubMed  CAS  Google Scholar 

  • Fragkaki AG, Koupparis MA, Georgakopoulos CG (2004) Quantitative structure–retention relationship study of α-, β1-, and β2-agonists using multiple linear regression and partial least-squares procedures. Anal Chem Acta 512:165–171

    Article  CAS  Google Scholar 

  • Gemma S, Kukreja G, Fattorusso C, Persico M, Romano MP, Altarelli M, Savini L, Campiani G, Fattorusso E, Basilico N, Taramelli D, Yardley V, Butini S (2006) Synthesis of N1-arylidene-N2-quinolyl- and N2-acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains. Bioorg Med Chem Lett 16:5384–5388

    Article  PubMed  CAS  Google Scholar 

  • Golbraikh A, Tropsha A (2002) Beware of q2!. J Mol Graph Model 20:269–276

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez-Diaz H, Prado-Prado FJ (2008) Unified QSAR and network-based computational chemistry approach to antimicrobials, part 1: multispecies activity models for antifungals. J Comput Chem 29(4):656–667

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez-Diaz H, Vilar S, Santana L, Uriarte E (2007) Medicinal chemistry and bioinformatics-current trends in drugs discovery with networks topological indices. Curr Top Med Chem 7(10):1015–1029

    Article  PubMed  CAS  Google Scholar 

  • Gonzalez-Diaz H, Gonzalez-Diaz Y, Santana L, Ubeira FM, Uriarte E (2008) Networks and connectivity indices. Proteomics 8(4):750–778

    Article  PubMed  CAS  Google Scholar 

  • Hansch C, Fujita T (1964) p–σ–π analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616–1626

    Article  CAS  Google Scholar 

  • Hansch C, Leo A, Unger SH, Kim KH, Nikaitani D, Lien EJ (1973) Aromatic substituent constants for structure-activity correlations. J Med Chem 16(11):1207–1216

    Article  PubMed  CAS  Google Scholar 

  • Hatya SA, Aki-sener E, Tekiner-Gulbas B, Yildiz I, Temiz-Arpaci O, Yalcin I, Altanlar N (2006) Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones. Eur J Med Chem 41:1398–1404

    Article  Google Scholar 

  • Ivanciuc O, Ivancicu T, Balaban AT (2002) QSAR models for the dermal penetration of polycyclic aromatic hydrocarbons. Internet Electron J Mol Des 1:559–571

    CAS  Google Scholar 

  • Kalsi R, Pande K, Bhalla TN, Bartwall JP, Gupta GP, Parmar SS (1990) Anti-inflammatory activity of quinazolinoformazans. J Pharm Sci 79(4):317–319

    Article  PubMed  CAS  Google Scholar 

  • Kier LB, Hall LH (1976) Molecular connectivity in chemistry and drug research. Academic press, New York, pp 129–145

    Google Scholar 

  • Kim YM, Farrah S, Baney RH (2007) Structure–antimicrobial activity relationship for silanols, a new class of disinfectants, compared with alcohols and phenols. Int J Antimicrob Agents 29:217–222

    Article  PubMed  CAS  Google Scholar 

  • Kumar A, Sharma P, Gurram VK, Rane N (2006) Studies on synthesis and evaluation of quantitative structure–activity relationship of 10-methyl-6-oxo-5-arylazo-6,7-dihydro-5H[1,3]azaphospholo[1,5-d][1,4]benzodiazepin-2-phospha-3-ethoxycarbonyl-1-phosphorus dichlorides. Bioorg Med Chem Lett 16:2484–2491

    Article  PubMed  CAS  Google Scholar 

  • Kumar A, Narasimhan B, Kumar D (2007) Synthesis, antimicrobial, and QSAR studies of substituted benzamides. Bioorg Med Chem 15:4113–4124

    Article  PubMed  CAS  Google Scholar 

  • Kumar P, Narasimhan B, Sharma D (2008) Synthesis, antimicrobial evaluation and QSAR analysis of substituted benzoic acid benzylidene/furan-2-yl-methylene hydrazides. ARKIVOC xiii:159–178

    Google Scholar 

  • Kumar P, Narasimhan B, Sharma D, Judge V, Narang R (2009) Hansch analysis of substituted benzoic acid benzylidene/furan-2-yl-methylene hydrazides as antimicrobial agents. Eur J Med Chem 44:1853–1863

    Article  PubMed  CAS  Google Scholar 

  • Leite ACL, DE Lima RS, Moreira DR, Cardoso MV, De Brito ACG, Dos Santos LMF, Hernandes MZ, Kipustok AC, de Lima RS, Soares MBP (2006) Synthesis, docking and in vitro activity of thiosemicarbazones, aminoacyl-thiosemicarbazides and acyl-thiazolidones against trypanosoma. Bioorg Med Chem 14:3749–3757

    Article  PubMed  CAS  Google Scholar 

  • Metwally KM, Abdel-Aziz LM, Lashine EM, Husseiny M, Badaway RH (2006) Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: synthesis and preliminary evaluation as antimicrobial agent. Bioorg Med Chem 14:8675–8682

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Kothawade UR, Pharande DS, Mourya VK, Dhake AS (2003) Syntheses and QSAR studies of sorbic, cinnamic and ricinoleic acid derivatives as potential antbacterial agents. Indian J Chem 42(B):2828–2834

    Google Scholar 

  • Narasimhan B, Belasare D, Pharande D, Mourya V, Dhake A (2004) Esters, amides and substituted derivatives of cinnamic acid; synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 39:827–834

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Mourya VK, Dhake AS (2006a) Design, synthesis, antibacterial and QSAR studies of myristic acid derivatives. Bioorg Med Chem Lett 16:3023–3029

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Kumari M, Jain N, Dhake AS, Sundaravelan C (2006b) Correlation of antibacterial activity of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl]-carboxamide and 3-substituted-5-(2-furanyl)-2-methyl-3H-thieno[2,3-d]pyrimidin-4-ones with topological indices using Hansch analysis. Bioorg Med Chem Lett 16:4951–4958

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Judge V, Narang R, Ohlan S, Ohlan R (2007a) Quantitative structure–activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives. Bioorg Med Chem Lett 17:5836–5845

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Dhake AS, Mourya VK (2007b) QSAR studies of 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridines aspotent angiotensin II receptor antagonists by MLR and NLR analysis. ARKIVOC i:189–204

    Google Scholar 

  • Narasimhan B, Mourya VK, Dhake AS (2007c) QSAR studies of antibacterial ricinoleic acid derivatives. Pharm Chem J 3:120–125

    Google Scholar 

  • Narasimhan B, Narang R, Judge V, Ohlan S, Ohlan R (2007d) Synthesis, antimicrobial and QSAR studies of substituted anilides. ARKIVOC xv:112–126

    Google Scholar 

  • Nayyar A, Monga V, Malde A, Coutinho E, Jain R (2007) Synthesis, anti-tuberculosis activity and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines. Bioorg Med Chem 15:626–640

    Article  PubMed  CAS  Google Scholar 

  • Pharmacopoeia of India (2007) Controller of publications, ministry of health department, vol 1. Government of India, New Delhi, p 37

  • Prado-Prado FJ, Gonzalez-Diaz H, Vega OMDL, Ubeira FM, Chou KC (2008) Unified QSAR approach to antimicrobials. Part 3: first multi-tasking QSAR model for input-coded prediction, structural back-projection, and complex networks clustering of antiprotozoal compounds. Bioorg Med Chem 16(11):5871–5880

    Article  PubMed  CAS  Google Scholar 

  • Randic M (1975) Characterization of molecular branching. J Am Chem Soc 97:6609–6615

    Article  CAS  Google Scholar 

  • Randic M (1993) Comparative regression analysis. Regressions based on a single descriptor. Croat Chem Acta 66:289–312

    CAS  Google Scholar 

  • Rodriguez-Arguelles MC, Lopez-Silva EC, Sanmartin J, Pelagatti P, Zani F (2005) Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: inhibitory activity against fungi and bacteria. J Inorg Biochem 99:2231–2239

    Article  PubMed  Google Scholar 

  • Schaper KJ (1999) Free-Wilson-type analysis of non-additive substituent effects on THPB dopamine receptor affinity using artificial neural networks. Quant Struct Act Relat 18:354–360

    Article  CAS  Google Scholar 

  • Sharma P, Kumar A, Sharma M (2006) Synthesis and QSAR studies on 5-[2-(2-methylprop-1-enyl)-1Hbenzimidazol-1yl]-4,6-diphenyl-pyrimidin-2-(5H)-thione derivatives as antibacterial. Eur J Med Chem 41:833–840

    Article  PubMed  CAS  Google Scholar 

  • Smalley TL, Peat AJ, Boucheron JA, Dickerson S, Garrido D, Preugschat F, Schweiker SL, Thomson SA, Wang TY (2006) Synthesis and evaluation of novel heterocyclic inhibitors of GSK-3. Bioorg Med Chem Lett 16:2091–2094

    Article  PubMed  CAS  Google Scholar 

  • SPSS for windows (1999) version 10.05. SPSS Inc., Bangalore, India

    Google Scholar 

  • Sztanke K, Pasterhak K, Rzymowska J, Sztanke M, Kandefer-Szerszen M (2007) Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. Eur J Med Chem 43(2):404–419

    Article  PubMed  Google Scholar 

  • Tanitame A, Oyamada-Ofuji K, Fujimob M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wachi M, Yamagishi J (2004) Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring. Bioorg Med Chem 12:5515–5524

    Article  PubMed  CAS  Google Scholar 

  • TSAR 3D (2000) Version 3.3. Oxford Molecular Limited

  • Vittorio F, Ronsisvalle G, Marrazzo A, Blandini G (1995) Synthesis and antimicrobial evaluation of 4-phenyl-3-isoquinolinoyl-hydrazones. Farmaco 50:265–272

    PubMed  CAS  Google Scholar 

  • Wiener H (1947) Structural determination of paraffin boiling points. J Am Chem Soc 69:17–20

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Swami Devi Dyal Institute of Pharmacy, Barwala, Panchkula, 134009, India

    Davinder Kumar

  2. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    Rakesh Narang & Vikramjeet Judge

  3. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    Devinder Kumar

  4. Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, 124001, India

    Balasubramanian Narasimhan

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  1. Davinder Kumar
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  2. Rakesh Narang
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  3. Vikramjeet Judge
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  4. Devinder Kumar
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  5. Balasubramanian Narasimhan
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Correspondence to Balasubramanian Narasimhan.

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Kumar, D., Narang, R., Judge, V. et al. Antimicrobial evaluation of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides and QSAR studies. Med Chem Res 21, 382–394 (2012). https://doi.org/10.1007/s00044-010-9543-7

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  • DOI: https://doi.org/10.1007/s00044-010-9543-7

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