Design of cinnamaldehyde amino acid Schiff base compounds based on the quantitative structure–activity relationship

Cinnamaldehyde amino acid Schiff base (CAAS) is a new class of safe, bioactive compounds which could be developed as potential antifungal agents for fungal infections. To design new cinnamaldehyde amino acid Schiff base compounds with high bioactivity, the quantitative structure–activity relationships (QSARs) for CAAS compounds against Aspergillus niger (A. niger) and Penicillium citrinum (P. citrinum) were analysed. The QSAR models (R2 = 0.9346 for A. niger, R2 = 0.9590 for P. citrinum,) were constructed and validated. The models indicated that the molecular polarity and the Max atomic orbital electronic population had a significant effect on antifungal activity. Based on the best QSAR models, two new compounds were designed and synthesized. Antifungal activity tests proved that both of them have great bioactivity against the selected fungi.

[1]  Joseph Rebehmed,et al.  Molecular modeling studies of N-substituted pyrrole derivatives--potential HIV-1 gp41 inhibitors. , 2008, Bioorganic & medicinal chemistry.

[2]  Gabriel Ramos-Ortiz,et al.  Synthesis and non-linear optical characterization of novel borinate derivatives of cinnamaldehyde , 2009 .

[3]  Kunal Roy,et al.  QSAR Studies of CYP2D6 Inhibitor Aryloxypropanolamines Using 2D and 3D Descriptors , 2009, Chemical biology & drug design.

[4]  Wenjun Li,et al.  Biodiversity, bioactive natural products and biotechnological potential of plant-associated endophytic actinobacteria , 2011, Applied Microbiology and Biotechnology.

[5]  Daohang He,et al.  Synthesis, biological evaluation, and structure-activity relationship study of novel stilbene derivatives as potential fungicidal agents. , 2015, Journal of agricultural and food chemistry.

[6]  A. Bianucci,et al.  QSAR study on a novel series of 8-azaadenine analogues proposed as A1 adenosine receptor antagonists. , 2008, European journal of medicinal chemistry.

[7]  Svetoslav H. Slavov,et al.  Rapid QSPR model development technique for prediction of vapor pressure of organic compounds , 2007, Comput. Chem. Eng..

[8]  Daniel Cabrol-Bass,et al.  Estimation of the Liquid Viscosity of Organic Compounds with a Quantitative Structure-Property Model , 1999, J. Chem. Inf. Comput. Sci..

[9]  D. E. Patterson,et al.  Crossvalidation, Bootstrapping, and Partial Least Squares Compared with Multiple Regression in Conventional QSAR Studies , 1988 .

[10]  Fei-Fei Gan,et al.  Structure-activity analysis of 2'-modified cinnamaldehyde analogues as potential anticancer agents. , 2009, Biochemical and biophysical research communications.

[11]  Randall J. Bernot,et al.  Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure–property relationship modeling , 2006 .

[12]  T. Stanojković,et al.  Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. , 2011, Bioorganic & medicinal chemistry letters.

[13]  S. Ignacimuthu,et al.  Cinnamaldehyde--a potential antidiabetic agent. , 2007, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[14]  Zhide Hu,et al.  Quantitative Structure-Retention relationship study of the constituents of saffron aroma in SPME-GC-MS based on the projection pursuit regression method. , 2008, Talanta.

[15]  Shibin Shang,et al.  Synthesis and quantitative structure–activity relationship (QSAR) studies of novel rosin-based diamide insecticides , 2014 .

[16]  M. K. Kathiravan,et al.  The biology and chemistry of antifungal agents: a review. , 2012, Bioorganic & medicinal chemistry.

[17]  Shujun Li,et al.  Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids. , 2016, Bioorganic & medicinal chemistry letters.

[18]  Thi Thanh Hien Nguyen,et al.  Quantitative structure-activity relationship of antifungal activity of rosin derivatives. , 2015, Bioorganic & medicinal chemistry letters.

[19]  T. Magalhães,et al.  Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity , 2015 .

[20]  M. Fatemi,et al.  In silico prediction of nematic transition temperature for liquid crystals using quantitative structure–property relationship approaches , 2009, Molecular Diversity.

[21]  K. Kaiser,et al.  Quantitative structure-toxicity relationship of halogenated phenols on bacteria , 1982, Bulletin of environmental contamination and toxicology.

[22]  Ning Li,et al.  Enhancement of the antimicrobial activity of cinnamon essential oil-loaded electrospun nanofilm by the incorporation of lysozyme , 2017 .

[23]  G Narahari Sastry,et al.  Molecular modeling studies of pyridopurinone derivatives--potential phosphodiesterase 5 inhibitors. , 2007, Journal of molecular graphics & modelling.

[24]  Iva B. Stoyanova-Slavova,et al.  QSPR modeling of flash points: an update. , 2007, Journal of Molecular Graphics and Modelling.

[25]  J. Xiong,et al.  The antimicrobial activities of the cinnamaldehyde adducts with amino acids. , 2011, International journal of food microbiology.

[26]  Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents , 2013, Medicinal Chemistry Research.

[27]  B. Fan,et al.  Quantitative structure-retention relationships for organic pollutants in biopartitioning micellar chromatography. , 2007, Analytica chimica acta.

[28]  M. Kudrat-E-Zahan,et al.  Synthesis, characteristics, and antimicrobial activity of some complexes of Mn(II), Fe(III) Co(II), Ni(II), Cu(II), and Sb(III) containing bidentate Schiff base of SMDTC , 2015, Russian Journal of General Chemistry.

[29]  K. Ramasamy,et al.  4-Thiazolidinone derivatives: synthesis, antimicrobial, anticancer evaluation and QSAR studies , 2016 .

[30]  M. S. Khan,et al.  Antifungal activity of essential oils and their synergy with fluconazole against drug-resistant strains of Aspergillus fumigatus and Trichophyton rubrum , 2011, Applied Microbiology and Biotechnology.

[31]  C. Nantasenamat,et al.  Insights into antioxidant activity of 1-adamantylthiopyridine analogs using multiple linear regression. , 2014, European journal of medicinal chemistry.

[32]  M. Hakimi,et al.  Cinnamaldehyde Schiff Base Derivatives: A Short Review , 2012 .

[33]  Aladdin M. Srour,et al.  Synthesis, bioassay, and QSAR study of bronchodilatory active 4H-pyrano[3,2-c]pyridine-3-carbonitriles. , 2015, European journal of medicinal chemistry.

[34]  R. Scaffaro,et al.  Study on carvacrol and cinnamaldehyde polymeric films: mechanical properties, release kinetics and antibacterial and antibiofilm activities , 2012, Applied Microbiology and Biotechnology.