Synthesis of halogenated azo-aspirin analogues from natural product derivatives as the potential antibacterial agents

References

• Abd Halim AN , Ngaini Z . 2016. Synthesis and bacteriostatic activities of bis(thiourea) derivatives with variables chain length. J Chem. 2016:1–7.10.1155/2016/2739832
   Web of Science ®Google Scholar
• Akay C , Degim IT , Sayal A , Aydin A , Ozkan Y , Gul H . 2008. Rapid and simultaneous determination of acetylsalicylic acid, paracetamol, and their degradation and toxic impurity products by HPLC in pharmaceutical dosage forms. Turk J Med Sci. 38(2):167–173.
   Web of Science ®Google Scholar
• Ansari MA , Deshmukh SP , Khan R , Musaddiq M . 2014. Synthesis antimicrobial and anticancer evaluation of 1-Aryl-5-(o-methoxyphenyl)-2-S-benzyl isothiobiurets. Int J Med Chem. 2014:1–5.
   Google Scholar
• Becattini C , Agnelli G , Schenone A , Eichinger S , Bucherini E , Silingardi M , Bianchi M , Moia M , Ageno W , Vandelli MR , et al . 2012. Aspirin for preventing the recurrence of venous thromboembolism. N Engl J Med. 366(21):1959–1967.10.1056/NEJMoa1114238
   PubMed Web of Science ®Google Scholar
• Bissantz C , Kuhn B , Stahl M . 2010. A medicinal chemist’s guide to molecular interaction. J Med Chem. 53:5061–5084.10.1021/jm100112j
   PubMed Web of Science ®Google Scholar
• Brown S , Santa Maria JP , Walker S . 2013. Wall teichoic acids of gram-positive bacteria. Annu Rev Microbiol. 67:313–336.10.1146/annurev-micro-092412-155620
   PubMed Web of Science ®Google Scholar
• Cicala C , Ianora A , Fiorucci S , Calignano A , Bucci M , Gerli R , Santucci L , Wallace JL , Cirino G . 2000. NO-naproxen modulages inflammation, nociception and downregulates T cell response in rat Freund’s adjuvant arthritis. Br J Pharmacol. 130(6):1399–1405.10.1038/sj.bjp.0703449
   PubMed Web of Science ®Google Scholar
• Coates J . 2006. Interpretation of infrared spectra, a practical approach. Encycl Anal Chem. 1–23.
   Google Scholar
• Gull P , Hashim AA . 2015. Biological activity studies on metal complexes of macrocyclic schiff base ligand: synthesis and spectroscopic characterization. J Braz Chem Soc. 26(7):1331–1337.
   Web of Science ®Google Scholar
• Harrold MW , Zavod RM . 2013. Basic concepts in medicinal chemistry . Bethesda (MD): American Society of Health-System Pharmacists.
   Google Scholar
• Hinks D , Freeman HS , Nakpathom M , Sokolowska J . 2000. Synthesis and evaluation of organic pigments and intermediates. 1. Nonmutagenic benzidine analogs. Dyes Pigm. 44:199–207.10.1016/S0143-7208(99)00078-9
   Web of Science ®Google Scholar
• Ho BK , Ngaini Z , Neilsen PM , Hwang SS , Linton RE , Kong EL , Lee BK . 2017. Synthesis and anticancer activities of 4-[(Halophenyl)diazenyl]phenol and 4-[(Halophenyldiazenyl]phenyl aspirinate derivatives against nasopharyngeal cancer cell lines. J Chem. 2017:1–7.10.1155/2017/6760413
   Web of Science ®Google Scholar
• Hoey AJ , Jackson CM , Pegg GG , Sillence MN . 1996. Characteristics of cyanopindolol analugues active at the β3-adrenoreceptor in rat ileum. Br J Pharmacol. 119:564–568.10.1111/bph.1996.119.issue-3
   PubMed Web of Science ®Google Scholar
• Huang L , Mackenzie GG , Ouyang N , Sun Y , Xie G , Johnson F , Komninou D , Rigas B . 2010. The novel phosphor-non-steroidal anti-inflammatory drugs, OXT-328, MDC-22 and MDC-917, inhibit adjuvant-induced arthritis in rats. Br J Pharmacol. 162(7):1521–1533.
   Web of Science ®Google Scholar
• Jarrahpou AA , Motamedifar M , Pakshir K , Hadi N , Zarei M . 2004. Synthesis of novel azo schiff bases and their antibacterial and antifungal activities. Molecules. 9(10):815–824.10.3390/91000815
   PubMed Web of Science ®Google Scholar
• Li L , Gao HW , Ren JR , Chen L , Li YC , Zhao JF et al . 2007. Binding of Sudan II and IV to lecithin liposomes and E. coli membranes: insights into the toxicity of hydrophobic azo dyes. BMC Struct Biol. 7(16):1–9.
   PubMed Web of Science ®Google Scholar
• Morris GM , Huey R , Lindstrom W , Sanner MF , Belew RK , Goodsell DS , et al . 2009. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem. 30(16):2785–2791.10.1002/jcc.v30:16
   PubMed Web of Science ®Google Scholar
• Nordin NA , Chai TW , Tan BL , Choi CL , Halim AN , Hussain H , Ngaini N . 2017. Novel synthetic monothiourea aspirin derivatives bearing alkylated amines as potential antimicrobial agenst. J Chem. 2017:1–7.10.1155/2017/2378186
   Web of Science ®Google Scholar
• Odlaug TE . 1981. Antimicrobial activity of halogens. J Food Prot. 44(8):608–613.10.4315/0362-028X-44.8.608
   PubMed Web of Science ®Google Scholar
• Petnapapun K , Chavasiri W , Sompornpisut P . 2013. Structure-activity relationships of 3,3′-phenylmethylene-bis-4-hydroxylcoumarins: selective and potent inhibitors of gram-positive bacteria. Sci World J. 2013:1–11.10.1155/2013/178649
   Web of Science ®Google Scholar
• Piotto S , Concilio S , Sessa L , Diana R , Torrens G , Juan C , Caruso U , Iannelli P . 2017. Synthesis and antimicrobial studies of new antibacterial azo-compounds active against Staphylococcus aureus and Listeria monocytogenes . Molecules. 22(1372):1–10.
   Google Scholar
• Raghavendra KR , Kumar KA . 2013. Synthesis of some novel azo dyes and their dyeing, redox and antifungal properties. Int J Chemtech Res. 5(4):1756–1760.
   Google Scholar
• Tonelli M , Vazzana I , Tasso B , Biodo V , Sparatore F , Fermeglia M , Paneni MS , Posocco P , Pricl S , Colla PL , et al . 2009. Antiviral and cytotoxic activities of aminoarylazo compounds and aryltriazene derivatives. Bioorg Med Chem. 17:4425–4440.10.1016/j.bmc.2009.05.020
   PubMed Web of Science ®Google Scholar
• Trott O , Olson AJ . 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem. 31(2):455–461.
   PubMed Web of Science ®Google Scholar
• Vane JR , Botting RM . 2003. The mechanism of action of aspirin. Thromb Res. 110(5–6):255–258.10.1016/S0049-3848(03)00379-7
   PubMed Web of Science ®Google Scholar
• Warner TD , Nylander S , Whatling C . 2011. Anti-platelet theraphy: cyclo-oxygenase inhibition and the use of aspirin with particular regard to dual anti-platelet theraphy. Br J Clin Pharmacol. 72(4):619–633.10.1111/j.1365-2125.2011.03943.x
   PubMed Web of Science ®Google Scholar
• Zhong Z , Xing R , Liu S , Wang L , Cai S , Li P . 2008. Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro . Carbohydr Res. 343:556–570.
   Web of Science ®Google Scholar