Synthesis, antimicrobial, anti-biofilm evaluation, and molecular modelling study of new chalcone linked amines derivatives

References

• Ugale V, Patel H, Patel B, Bari S. Benzofurano-isatins: search for antimicrobial agents. Arab J Chem 2017;10:S389–S96.
   Web of Science ®Google Scholar
• Zhang X, Khalidi O, Kim SY, et al. Synthesis and biological evaluation of 5,7-dihydroxyflavanone derivatives as antimicrobial agents. Bioorg Med Chem Lett 2016;26:3089–92.
   PubMed Web of Science ®Google Scholar
• Sambanthamoorthy K, Neiditch MB, Sloup RE, et al. Identification of small molecules that antagonize diguanylate cyclase enzymes to inhibit Biofilm formation. Antimicrob Agents Chemother 2012;56:5202–11.
   PubMed Web of Science ®Google Scholar
• Hall-Stoodley L, Costerton JW, Stoodley P. Bacterial biofilms: from the natural environment to infectious diseases. Nat Rev Microbiol 2004; 2:95–108.
   PubMed Web of Science ®Google Scholar
• Hall-Stoodley L, Stoodley P. Evolving concepts in biofilm infections. Cell Microbiol 2009;11:1034–43.
   PubMed Web of Science ®Google Scholar
• (a) Cotter PA, Stibitz S. c-di-GMP-mediated regulation of virulence and biofilm formation. Curr Opin Microbiol 2007;10:17–23. (b) De N, Pirruccello M, Krasteva PV, et al. Phosphorylation-independent regulation of the diguanylate cyclase. WspR PLoS Biol 2008;6:67.
   PubMed Web of Science ®Google Scholar
• Dow JM, Fouhy Y, Lucey JF, Ryan RP. The HD-GYP domain, cyclic di-GMP signaling, and bacterial virulence to plants. Mol Plant Microbe Interact 2006;19:1378–84.
   PubMed Web of Science ®Google Scholar
• Sambanthamoorthy K, et al. Identification of a novel benzimidazole that inhibits bacterial biofilm formation in a broad-spectrum manner. Antimicrob Agents Chemother 2011;55:4369–78.
   PubMed Web of Science ®Google Scholar
• Sambanthamoorthy K, Schwartz A, Nagarajan V, Elasri MO. The role of msa in Staphylococcus aureus biofilm formation. BMC Microbiol 2008;8:221.
   PubMed Web of Science ®Google Scholar
• Schleheck D, Barraud N, Klebensberger J, et al. Pseudomonas aeruginosa PAO1 preferentially grows as aggregates in liquid batch cultures and disperses upon starvation. PLoS One 2009;4:e5513.
   PubMed Web of Science ®Google Scholar
• Sintim HO, Smith JA, Wang J, et al. Paradigm shift in discovering next-generation anti-infective agents: targeting quorum sensing, c-di-GMP signaling and biofilm formation in bacteria with small molecules. Future Med Chem 2010;2:1005–35.
   PubMed Web of Science ®Google Scholar
• Suwito H, Ni’matuzahroh AN, Kristanti S, et al. Antimicrobial activities and in silico analysis of methoxy amino chalcone derivatives. Proc Chem 2016;18:103–11.
   Google Scholar
• Kant R, Kumar D, Agarwal D, et al. Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities. Eur J Med Chem 2016;113:34–49.
   PubMed Web of Science ®Google Scholar
• Liaras K, Geronikaki A, Glamočlija J, et al. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation. Bioorg Med Chem 2011;19:3135–40.
   PubMed Web of Science ®Google Scholar
• Pedrosa O, Cruz D, da Viana O, et al. Hybrid compounds as direct multitarget ligands: a review. Curr Top Med Chem 2017;17:1044–79.
   PubMed Web of Science ®Google Scholar
• Kuppast B, Fahmy H. Thiazolo[4,5-d]pyrimidines as a privileged scaffold in drug discovery. Eur J Med Chem 2016;113:198–213.
   PubMed Web of Science ®Google Scholar
• Suwitoa H, Matuzahrohb N, Kristantia AN, et al., Antimicrobial activities and in silico analysis of methoxy amino chalcone derivatives. Proc Chem 2016;18:103–11.
   Google Scholar
• Suwito H, Ul Haq K, Rahmah NND, et al. 4-({4-[(2E)-3-(2,5-Dimethoxyphenyl)prop-2enoyl]phenyl}amino)-4-oxobutanoic acid. Molbank 2017;2017:M938.
   Web of Science ®Google Scholar
• Suwito H, Jumina M, Puspaningsih P. Anticancer and antimicrobial activity of methoxy amino chalcone derivatives. Pharm Chem 2015;7:89–94.
   Google Scholar
• Suwito H, Kristanti AN, Hayati S, et al. Antimicrobial activities and in silico analysis of methoxy amino chalcone derivatives. Proc Chem 2016;18:103–11.
   Google Scholar
• Hassan GS, El-Messery SM, Abbas A. Synthesis and anticancer activity of new thiazolo[3,2-a]pyrimidines: DNA binding and molecular modeling study. Bioorg Chem 2017;74:41–52.
   PubMed Web of Science ®Google Scholar
• El-Gazzar YI, Georgey HH, El-Messery SM, et al. Synthesis, biological evaluation and molecular modeling study of new (1,2,4-triazole or 1,3,4-thiadiazole)-methylthio-derivatives of quinazolin-4(3H)-one as DHFR inhibitors. Bioorg Chem 2017;72:282–92.
   PubMed Web of Science ®Google Scholar
• El-Subbagh HI, El-Azab AS, Hassan GS, et al. Thiadiazolodiazepine analogues as a new class of neuromuscular blocking agents: synthesis, biological evaluation and molecular modeling study. Eur J Med Chem 2017;126:15–23.
   PubMed Web of Science ®Google Scholar
• El-Subbagh HI, Hassan GS, El-Taher KEH, et al. Synthesis, biological evaluation and molecular modeling study of thiadiazolo[3,2-a][1,3]diazepine analogues of HIE-124 as a new class of short acting hypnotics. Eur J Med Chem 2016;124:237–47.
   PubMed Web of Science ®Google Scholar
• Siddiqui ZN, Praveen S, Musthafa MTN, et al. Thermal solvent-free synthesis of chromonyl chalcones, pyrazolines and their invitro antibacterial, antifungal activities. J Enzyme Inhibit Med Chem 2012;27:84.
   PubMed Web of Science ®Google Scholar
• Siddiqui ZN, Musthafa MTN, Ahmad A, Khan AU. Thermal solvent-free synthesis of novel pyrazolylchalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett 2011;21:2860.
   PubMed Web of Science ®Google Scholar
• Wayne PA, Clinical and Laboratory Standards Institute (CLSI). “Performance standards for antimicrobial susceptibility testing, 25th informational supplement”. 2015;M100:S15.
   Google Scholar
• Murray PR, Baron EJ, Pfaller MA, et al. Manual of clinical microbiology. Washington DC: ASM Press; 1995.
   Google Scholar
• Stepanovic S, Vukovic D, Dakic I, et al. A modified microtiter-plate test for quantification of staphylococcal biofilm formation. J Microbiol. Methods 2000;40:175–9.
   PubMed Web of Science ®Google Scholar
• Wassmann P, Chan C, Paul R, et al. Structure of Bef3–modified response regulator pled: implications for diguanylate cyclase activation, catalysis, and feedback inhibition. Structure 2007;15:915.
   PubMed Web of Science ®Google Scholar
• Profeta S, Allinger NL. Molecular mechanics calculations on aliphatic amines. J Am Chem Soc 1985;107:1907–18.
   Web of Science ®Google Scholar
• Allinger NL. Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms. J Am Chem Soc 1977;99:8127–34.
   Web of Science ®Google Scholar
• Labute P, Williams C, Feher M, et al. Flexible alignment of small molecules. J Med Chem 2001;44:1483–90.
   PubMed Web of Science ®Google Scholar
• Kearsley S, Smith GM. An alternative method for the alignment of molecular structures: maximizing electrostatic and steric overlap. Tetrahedron Comput Methodol 1990;3:615–33.
   Google Scholar
• Sambanthamoorthy K, Neiditch MB, Sloup RE, et al. Identification of small molecules that antagonize diguanylate cyclase enzymes to inhibit biofilm formation. Antimicrob Agents Chemother 2012;56:5202–11.
   PubMed Web of Science ®Google Scholar
• Tavares LC, Chisté JJ, Santos MGB, Penna TCV. Synthesis and biological activity of nifuroxazide and analogs II. Boll Chim Farm 1999;138:432.
   PubMedGoogle Scholar
• Masunari A, Tavares LC. A new class of nifuroxazide analogues: synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. Bioorg Med Chem 2007;15:4229–36.
   PubMed Web of Science ®Google Scholar
• Tavares LC, Penna TCV, Amaral AT. Synthesis and biological activity of nifuroxazide and analogs.  Boll Chim Farm 1997;136:244–9.
   PubMedGoogle Scholar
• Zhao Y, Abraham MH, Lee J, et al. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 2002;19: 1446–56.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3–25.
   Web of Science ®Google Scholar