Synthesis, Antimicrobial Evaluation and QSAR Studies of p-hydroxy Benzoic Acid Derivatives

 

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Abstract

In the present study, a series of p-hydroxy benzoic acid derivatives (1–29) was synthesized and tested for its antimicrobial potential. Results of antimicrobial studies indicated that in general, Schiff bases were found to be more active as compared to esters and compound 14 was found to be most potent antimicrobial agent (pMIC_am=1.50 µM/ml). QSAR study was performed in order to understand the relationship between antimicrobial activity and changes in the molecular structures which indicated that antimicrobial activity of the synthesized compounds was governed by valence first order molecular connectivity index (¹χ^v), Kier’s alpha first order shape index (κα₁), Kier’s first order shape index (κ₁) and Balaban topological index (J).

• References

• 1 Patel DH, Chikhalia KH, Shah NK et al. Design, synthesis and antimicrobial study of some pyrimidine derivatives. Pharm Chem J 2010; 44: 94-98
  CrossrefPubMedGoogle Scholar
• 2 Valkova N, Lepine F, Labrie L et al. Purification and characterization of prba, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (Parabens). J Biol Chem 2003; 278: 12779-12785
  CrossrefPubMedGoogle Scholar
• 3 Sigroha S, Narasimhan B, Kumar P et al. Design, synthesis, antimicrobial, anticancer evaluation, and QSAR studies of 4-(substituted benzylidene-amino)-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones. Med Chem Res 2012; 21: 3863-3875
  CrossrefPubMedGoogle Scholar
• 4 Judge V, Narasimhan B, Ahuja M et al. Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of isonicotinic acid-1-(substituted phenyl)-ethylidene/cycloheptylidene hydrazides. Med Chem Res 2012; 21: 1935-1952
  CrossrefPubMedGoogle Scholar
• 5 Judge V, Narasimhan B, Ahuja M et al. Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity and QSAR studies. Med Chem Res 2012; 21: 1451-1470
  CrossrefPubMedGoogle Scholar
• 6 Denyer SP, Hodges NA, Gorman SP. In Hugo and Russels Pharmaceutical microbiology; 7^th ED. Blackwell Science; Oxford: 2004: 103
  CrossrefGoogle Scholar
• 7 Hansch C, Fujita T. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 1964; 86: 1616-1626
  CrossrefPubMedGoogle Scholar
• 8 Golbraikh A, Tropsha A. Beware of q² . J Mol Graphics Model 2002; 20: 269-276
  CrossrefPubMedGoogle Scholar
• 9 Schaper KJ. Free-Wilson-type analysis of non-additive substituent effects on THPB dopamine receptor affinity using artificial neural networks. Free-Wilson-type analysis of non-additive substituent effects on THPB dopamine receptor affinity using artificial neural networks. Quant Struct Act Relat 1999; 18: 354-360
  CrossrefPubMedGoogle Scholar
• 10 Cappucino JG, Sherman N. Microbiology – A Laboratory Manual. Addison Wesley; California: 1999: 263
  Google Scholar