Synthesis, antimicrobial evaluation and QSAR studies of p-amino benzoic acid derivatives
Home >
2014,
Vol. 2 No. 1 > Synthesis, antimicrobial evaluation and QSAR studies of p-amino benzoic acid derivatives
Authors
- MeetaFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak-124001, India
- Pradeep KumarFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak-124001, India
- Balasubramanian NarasimhanFaculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak-124001, India
Keywords
PABA, Synthesis, Antimicrobial, mt-QSAR, LOO method
Abstract
A series of Schiff bases (1-16) and esters (17-27) of p-amino benzoic acid (PABA) was synthesized and its in vitro antimicrobial potential was evaluated by using tube dilution method. Compound 11 was found to be most promising antibacterial agent (pMICbs = 2.11 μM/ml) having antibacterial potential comparable to standard drug norfloxacin (pMICbs = 2.61 μM/ml) and may be taken as a lead compound for the development of novel antibacterial agents. QSAR analysis indicated that electronic parameters, total energy (Te) and energy of lowest unoccupied molecular orbital (LUMO) were found dominant in explaining the antimicrobial activity of synthesized compounds.
References
- Akberova, S.I. (2002). New biological properties of p-aminobenzoic acid. Biological Bulletin, 29, 390-393. https://doi.org/10.1023/A:1016871219882.
- Cappucino, J.G. & Sherman, N. (1999). Microbiology —A Laboratory Manual. Addison Wesley, California; 263.
- Chhonker, Y.S., Veenu, B., Hasim, S.R., Kaushik, N., Kumar, D. & Kumar, P. (2009). Synthesis and pharmacological evaluation of some new 2-phenyl benzimidazoles derivatives and their Schiff’s bases. E-Journal of Chemistry, 6(S1), S342-S346. http://dx.doi.org/10.1155/2009/604203.
- 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. https://doi.org/10.1016/j.chemosphere.2005.07.002.
- Golbraikh, A. & Tropsha, A. (2002). Beware of q2! Journal of Molecular Graphics and Modeling, 20, 269-276. https://doi.org/10.1016/S1093-3263(01)00123-1.
- Gonzalez-Diaz, H. & Prado-Prado, F.J. (2008). Unified QSAR and network-based computational chemistry approach to antimicrobials, part 1: Multispecies activity models for antifungals. Journal of Computational Chemistry, 4, 656-667. https://doi.org/10.1002/jcc.20826.
- Gonzalez-Diaz, H., Gonzalez-Diaz, Y., Santana, L., Ubeira, F.M., & Uriarte, E. (2008). Networks and connectivity indices. Proteomics, 4, 750-778. https://doi.org/10.1002/pmic.200700638.
- Gonzalez-Diaz, H., Vilar, S., Santana, L. & Uriarte, E. (2007). Medicinal chemistry and bioinformatics-current trends in drugs discovery with networks topological indices. Current Topics in Medicinal Chemistry, 10, 1015-1029. https://doi.org/10.1002/pmic.200700638.
- Hansch, C. & Fujita, T.C. (1964). Fujita p-σ-π Analysis. A method for the correlation of biological activity and chemical structure. Journal of American Chemical Society, 86, 1616-1626. https://doi.org/10.1021/ja01062a035.
- Hyperchem 6.0 (1993). Hypercube, Inc., Florida.
- Kumar, A., Narasimhan, B. & Kumar, D. (2007). Synthesis, antimicrobial, and QSAR studies of substituted benzamides. Bioorganic Medicinal Chemistry, 15, 4113-4124. https://doi.org/10.1016/j.bmc.2007.03.074.
- Narasimhan, B., Ohlan, S., Ohlan, R., Judge, V. & Narang, R. (2009). Hansch analysis of veratric acid derivatives as antimicrobial agents. European Journal of Medicinal Chemistry, 44(2), 689-700. https://doi.org/10.1016/j.ejmech.2008.05.008.
- Narasimhan, B., Saharan, R. & Kumar, P. (2011). Hansch analysis of anti-inflammatory and analgesic activities of substituted 1-alkyl/aryl-3-ethoxy carbonyl-5-hydroxy-2-methyl indoles. Acta Pharma Scientia, 53, 117-126.
- Pharmacopoeia of India (2007). Controller of Publications, Ministry of Health Department, Govt. of India, New Delhi, 1, 37.
- Sabet, R., Mohammadpour, M., Sadeghi, M. & Fassihi, A. (2010). QSAR study of isatin analogues as in vitro anticancer agents. European Journal of Medicinal Chemistry, 45, 1113-1118. https://doi.org/10.1016/j.ejmech.2009.12.010.
- Sortino, M., Delgado, P., Jaurez, S., Quiroga, J., Abonia, R., Insuasey, B., Rodero, M.N., Garibotto, F.M., Enriz, R.D. & Zaccino, S.A. (2007). Bioorganic Medicinal Chemistry 15, 484-494. https://doi.org/10.1016/j.bmc.2006.09.038.
- SPSS for Windows, version 10.05 (1999). SPSS Inc., Bangalore, India.
- TSAR 3D Version 3.3 (2000). Oxford Molecular Limited.
- Zasloff, M. (2002). Antimicrobial peptides of multicellular organisms. Nature, 415, 389-395 https://doi.org/10.1038/415389a.
How to Cite
Meeta, Pradeep Kumar, Balasubramanian Narasimhan. Synthesis, antimicrobial evaluation and QSAR studies of p-amino benzoic acid derivatives.
J. Pharm. Technol. Res. Manag.. 2014, 02, 87-104