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Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives

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Abstract

A series of 2-amino benzoic acid derivatives (1–28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives.

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References

  • Agrawal VK, Singh J, Mishra KC, Khadikar PV, Jaliwala YA (2006) QSAR study on 5,6-dihydro-2-pyrones as HIV-1 protease inhibitors. ARKIVOC ii:162–177

  • 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 manual. Addison Wesley Longman Inc, California, p 263

    Google Scholar 

  • Cocco MT, Congiu C, Lilliu V, Onnis V (2004) Synthesis of new N-(2-(trifluoromethyl)pyridin-4-yl)anthranilic acid derivatives and their evaluation as anticancer agents. Bioorg Med Chem Lett 14:5787–5791

    Article  PubMed  CAS  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 

  • Dambrosio L, Dilorenzo S, Iaccarino P (1965) Clinical research on the diuretic and saluretic activity of chloro-n-(2-furylmethyl)-5-sulfamyl-anthranilic acid. Clin Ter 33:3–19

    CAS  Google Scholar 

  • Emami S, Falahati M, Banifafemi A, Shafiee A (2004) Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers. Bioorg Med Chem 12:5881–5889

    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 

  • Furusjo E, Svenson A, Rahmberg M, Andersson M (2006) The importance of outlier detection and training set selection for reliable environmental QSAR predictions. Chemosphere 63:99–108

    Article  PubMed  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, 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 

  • Gupta SP, Kumar AN, Nagazppa AN, Kumar D, Kumaran S (2003) A quantitative structure–activity relationship study on a novel class of calcium-entry blockers: 1-[{4-(aminoalkoxy) phenyl}sulphonyl] indolizines. Eur J Med Chem 38:867–873

    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 16:1207–1216

    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 

  • Inglis JJ, Criado G, Andrews M, Feldmann M, Williams RO, Selley ML (2007) The anti-allergic drug, N-(3′,4′-dimethoxycinnamonyl) anthranilic acid, exhibits potent anti-inflammatory and analgesic properties in arthritis. Rheumatology (Oxford) 46(9):1428–1432

    Article  CAS  Google Scholar 

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

    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

  • Lather V, Madan AK (2005) Topological models for the prediction of anti-HIV activity of dihydro (alkylthio) (naphthylmethyl) oxopyrimidines. Bioorg Med Chem 13:1599–1604

    Article  PubMed  CAS  Google Scholar 

  • Minu M, Thangadurai S, Wakode S, Aggarwal SS, Narasimhan B (2008) 3,4-Disubstituted-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones: synthesis, antimicrobial evaluation and QSAR investigations using Hansch analysis. Arch Pharm (Weinheim) 341:231–239

    Article  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, Kumari M, Jain N, Dhake AS, Sundaravelan C (2006a) 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, Mourya VK, Dhake AS (2006b) Design, synthesis, antibacterial and QSAR studies of myristic acid derivatives. Bioorg Med Chem Lett 16:3023–3029

    Article  PubMed  CAS  Google Scholar 

  • Narasimhan B, Mourya VK, Dhake AS (2007a) QSAR studies of antibacterial ricinoleic acid derivatives. Pharm Chem J 41(3):16–21

    Article  Google Scholar 

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

  • Narasimhan B, Judge V, Narang R, Ohlan S, Ohlan R (2007c) 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 

  • Pasha FA, Srivastva HK, Beg Y, Singh PP (2006) DFT based electrophilicity index and QSAR study of phenols as anti leukaemia agent. Am J Immunol 2(1):23–28

    Article  CAS  Google Scholar 

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

  • Pillai AD, Rani S, Rathod PD, Xavier FP, Vasu KK, Padh H, Sundarsanam V (2005) QSAR studies on some thiophene analogs as anti-inflammatory agents: enhancement of activity by electronic parameters and its utilization for chemical lead optimization. Bioorg Med Chem 13:1275–1283

    Article  PubMed  CAS  Google Scholar 

  • 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 

  • Raman N, Joseph JS, Kumar M, Sujatha S, Sahayaraj K (2008) Insecticidal activity of the schiff-base derived from anthranilic acid and acetoacetanilide and its copper complex on Spodoptera litura (Fab.). J Biopestic 1(2):206–209

    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 

  • Selvam P, Babu K, Padamraj R, Persoons L, Clercq E (2008) Synthesis, antiviral and cytotoxic activities of some novel 2-phenyl-3-disubstituted quinazolin-4(3H)-ones. Afr J Pharm Pharmcol 2(6):110–115

    Google Scholar 

  • Sharma P, Rane N, Gurram VK (2004) Synthesis and QSAR studies of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents. Bioorg Med Chem Lett 14:4185–4190

    Article  PubMed  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 

  • Simons LJ, Caprathe BW, Callahan M, Graham JM, Kimura T, Lai Y, LeVine H, Lipinski W, Sakkab AT, Tasaki Y, Walker LC, Yasunaga T, Ye Y, Zhuang N, Augelli-Szafran CE (2009) The synthesis and structure–activity relationship of substituted N-phenyl anthranilic acid analogs as amyloid aggregation inhibitors. Bioorg Med Chem Lett 19:654–657

    Article  PubMed  CAS  Google Scholar 

  • Sortino M, Delgado P, Jaurez S, Quiroga J, Abonia R, Insuasey B, Nogueras M, Rodero L, Garibotto FM, Enriz RD, Zacchino SA (2007) Synthesis and antifungal activity of (Z)-5-arylidenerhodanines. Bioorg Med Chem 15:484–494

    Article  PubMed  CAS  Google Scholar 

  • Sperandio GM, Sant’Anna CMR, Barreiro EJ (2004) A noval 3D-QSAR comparative molecular field analysis (COMFA) model of imidazole and quinazolinone functionalized p38 MAP kinase inhibitors. Bioorg Med Chem Lett 14:3159–3166

    Google Scholar 

  • TSAR 3D Version 3.3, Oxford Molecular Limited, 2000

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

    Kuldeep Mahiwal, Pradeep Kumar & Balasubramanian Narasimhan

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  1. Kuldeep Mahiwal
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  2. Pradeep Kumar
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  3. Balasubramanian Narasimhan
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Correspondence to Balasubramanian Narasimhan.

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Mahiwal, K., Kumar, P. & Narasimhan, B. Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives. Med Chem Res 21, 293–307 (2012). https://doi.org/10.1007/s00044-010-9537-5

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  • DOI: https://doi.org/10.1007/s00044-010-9537-5

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