In silico toxicity prediction, synthesis, characterization, antimicrobial and antioxidant activity of different di substituted chalcones

Letters in Applied NanoBioScience

Volumn 9, Issue 1, 2020, Pages 908-913

  Ammaji, Shaik ^a   Sunddep, Cheekurthi ^a   Sandeep, Koduru ^a   Ashok, Kunchala ^a   Praveen, Kancharala ^a   Murali, Badugu Sai ^a  

^a NRI College of Pharmacy   (India)

Author keywords

antimicrobial activity; antioxidant; molinspiration; ochem; Osiris; preADME

Indexed keywords

EID: 85085557233     PISSN: None     EISSN: 22846808     Source Type: Journal    
DOI: 10.33263/LIANBS91.908913     Document Type: Article

References (36)

1. Elavarasan, M.; Thendral, M.T.; Shafi, S.S.Ayntheisis and biological evaluation of chalcone derivatives. Inter jour pharm scien and research 2018, 9, 1969-1973, https://doi.org/10.13040/IJPSR.0975-8232.9(5).1969-73.
2. Ni, L.; Meng, C.Q.; Sikorski, J.A. Recent advances in therapeutic chalcones. Expert Opinion on Therapeutic Patents 2004, 14, 1669-1691, https://doi.org/10.1517/13543776.14.12.1669.
3. Sahu, N.K.; Balbhadra, S.S.; Choudhary, J.; Kohli, D.V. Exploring pharmacological significance of chalcone scaffold: A review. Curr. Med. Chem.2012, 19, 209– 225,https://doi.org/10.2174/092986712803414132.
4. Gomes, M.N.; Muratov, E.N.; Pereira, M.; Peixoto, J.C.; Rosseto, L.P.; Cravo, P.V.L.; Andrade, C.H.; Neves, B.J. Chalcone Derivatives: Promising Starting Points for Drug Design. Molecules 2017, 22, 1210, https://doi.org/10.3390/molecules22081210.
5. Evranos, A.B.; Ertan, R. Chemical and structural properties of chalcones I. FABAD J. Pharm. Sci.2011, 36, 223–242.
6. Kim, D.W.; Curtis-Long, M.J.; Yuk, H.J.; Wang, Y.; Song, Y.H.; Jeong, S.H.; Park, K.H. Quantitative analysis of phenolic metabolites from different parts of Angelica keiskei by HPLC– ESI MS/MS and their xanthine oxidase inhibition. Food Chem.ol2014,153,20–27. http://dx.doi.org/10.1016/j.foodchem.2013.12.026.
7. Yamamoto, T.; Yoshimura, M.; Yamaguchi, F.; Kouchi, T.; Tsuji, R.; Saito, M.; Obata, A.; Kikuchi, M. Anti-allergic activity of naringeninchalcone from a tomato skin extract. Biosci. Biotechnol. Biochem.2004, 68, 1706– 171,https://doi.org/10.1271/bbb.68.1706.
8. Aoki, N.; Muko, M.; Ohta, E.; Ohta, S. C-geranylatedchalcones from the stems of Angelica keiskei with superoxide-scavenging activity. J. Nat. Prod.2008, 71, 2008, 1308–1310,https://doi.org/10.1021/np800187f.
9. Birari, R.B.; Gupta, S.; Mohan, C.G.; Bhutani, K.K. Antiobesity and lipid lowering effects of Glycyrrhizachalcones: Experimental and computational studies. Phytomedicine2011, 18, 795–801, https://doi.org/10.1016/j.phymed.2011.01.002.
10. Chen, M.; Christensen, S.B.; Blom, J.; Lemmich, E.; Nadelmann, L.; Fich, K.; Theander, T.G.; Kharazmi, A. Licochalcone A, a novel antiparasitic agent with potent activity against human pathogenic protozoan species of Leishmania. Antimicrob. Agents Chemother. 1993, 37, 2550–2556, https://dx.doi.org/10.1128%2Faac.37.12.2550.
11. Cho, S.; Kim, S.; Jin, Z.; Yang, H.; Han, D.; Baek, N.I.; Jo, J.; Cho, C.W.; Park, J.H.; Shimizu, M.; Jin, Y.H.Isoliquiritigenin, a chalcone compound, is a positive allosteric modulator of GABA A receptors and shows hypnotic effects. Biochem.Biophys. Res. Commun. 2011,413, 637– 642,https://doi.org/10.1016/j.bbrc.2011.09.026.
12. Fowler, K.; Fields, W.; Hargreaves, V.; Reeve, L.; Bombick, B. Development, qualification, validation and application of the Ames test using a VITROCELL® VC10® smoke exposure system. Toxicology Reports 2018, 5, 542-551, https://doi.org/10.1016/j.toxrep.2018.04.003.
13. Dillon, D.; Combes, R.; Zeiger, E. The effectiveness of Salmonella strains TA100, TA102 and TA104 for detecting mutagenicity of some aldehydes and peroxides. Mutagenesis 1998, 13, 19-26, https://doi.org/10.1093/mutage/13.1.19.
14. Miller, W.H.; Dessert, A.M.; Roblin, jr.R.O.heterocyclicsulphonamides as a cabonic anhydrase inhibitors. J. Am. Chem. Soc.1950,72,4893-4896, https://doi.org/10.1021/ja01167a012.
15. Sushko, I.; Novotarskyi, S.; Korner, R.; Pandey, A.K.; Rupp, M.; Teetz, W.; Brandmaier, S.; Abdelaziz, A.; Prokopenko, V.V.; Tanchuk, V.Y.; Todeschini, R.; Varnek, A.; Marcou, G.; Ertl, P.; Potemkin, V.; Grishina, M.; Gasteiger, J.; Schwab, C.; Baskin, II; Palyulin, V.A.; Radchenko, E.V.; Welsh, W.J.; Kholodovych, V.; Chekmarev, D.; Cherkasov, A.; Aires-de-Sousa, J.; Zhang, Q.Y.; Bender, A.; Nigsch, F.; Patiny, L.; Williams, A.; Tkachenko, V.; Tekto, I.V. Online chemical modeling environment (OCHEM): web platform for data storage, model development and publishing of chemical information. Journal of computer-aided molecular design 2011, 25, 533-554, https://doi.org/10.1007/s10822-011-9440-2.
16. Aniceto, N.; Freitas, A.A.; Bender, A.; Ghafourian, T. A novel applicability domain technique for mapping predictive reliability across the chemical space of a QSAR: reliability-density neighbourhood. Journal of Cheminformatics 2016, 8, 69, https://doi.org/10.1186/s13321-016-0182-y.
17. Honda, H.; Minegawa, K.; Fujita, Y.; Yamaguchi, N.; Oguma, Y.; Glatt, H.; Nishiyama, N.; Kasamatsu, T. Modified Ames test using a strain expressing human sulfotransferase 1C2 to assess the mutagenicity of methyleugenol. Genes and Environment 2016, 38, 1, https://doi.org/10.1186/s41021-016-0028-x.
18. de Mello Silva Oliveira, N.; Reis Resende, M.; Alexandre Morales, D.; de RagãoUmbuzeiro, G.; Boriollo, M.F.G. In vitro mutagenicity assay (Ames test) and phytochemical characterization of seeds oil of Helianthus annuusLinné (sunflower). Toxicology reports 2016, 3, 733-739, https://doi.org/10.1016/j.toxrep.2016.09.006.
19. Prival, M.J.; Zeiger, E. Chemicals mutagenic in Salmonella typhimurium strain TA1535 but not in TA100. Mutation research 1998, 412, 251-260, https://doi.org/10.1016/s1383-5718(97)00196-4.
20. Daina, A.; Michielin, O.; Zoete, V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific reports 2017, 7, 42717, https://doi.org/10.1038/srep42717.
21. Claxton, L.D.; UmbuzeiroGde, A.; DeMarini, D.M. The Salmonella mutagenicity assay: the stethoscope of genetic toxicology for the 21st century. Environmental health perspectives 2010, 118, 1515-1522, https://doi.org/10.1289/ehp.1002336.
22. Sashidhara, K.V.; Rosaiah, J.N.; Kumar, A. Iodine-Catalyzed Mild and Efficient Method for the Synthesis of Chalcones. Synthetic Communications 2009, 39, 2288-2296, https://doi.org/10.1080/00397910802654724.
23. Mojžiš, J.; Sarisský, M.; Pilatova, M.; Voharová, V.; Varinska, L.; Mojzisová, G.; Ostro, A.; Urdzik, P.; Dankovcik, R.; Mirossay, L. In vitro antiproliferative and antiangiogenic effects of Flavin7®. Physiological research / Academia ScientiarumBohemoslovaca2008, 57, 413-420.
24. Kulathooran. S.; Dhamodaran, M. Synthesis And Biological Evaluation Of Some New Chalcones Using Anhydrous Potassium Carbonate As An Efficient Basic Catalyst By Conventional And Microwave Assisted Techniques.Ijpsr2015, 47, 3027-33.
25. Braca, A.; De Tommasi, N.; Di Bari, L.; Pizza, C.; Politi, M.; Morelli, I. Antioxidant principles from Bauhinia tarapotensis. Journal of natural products 2001, 64, 892-895, https://doi.org/10.1021/np0100845.
26. Khalil, N.S. Efficient synthesis of novel 1,2,4-triazole fused acyclic and 21-28 membered macrocyclic and/or lariat macrocyclicoxaazathia crown compounds with potential antimicrobial activity. Eur J Med Chem2010, 45, 5265-5277, https://doi.org/10.1016/j.ejmech.2010.08.046.
27. Dhorajiya, B.D.;Dholakiya, B.Z. Design, Synthesis and Comparative Study of Anti-Microbial Activities on Barbituric Acid and Thiobarbituric Acid based Chalcone Derivatives Bearing the Pyrimidine Nucleus.ChemSci J2016,7, 1-9.
28. Opletalova, V.; Jahodar, L.; Jun, D.; Opletal, L. [Chalcones (1,3-diarylpropen-1-ones) and their analogs as potential therapeutic agents in cardiovascular system diseases]. Ceska a Slovenskafarmacie:casopis Ceske farmaceutickespolecnosti a Slovenskefarmaceutickespolecnosti2003, 52, 12-19.
29. Sambamoorthy, U.; Venkataraju, M.; Manjappa, A.; Rao, M. Gemcitabine-loaded Folic Acid Tagged Liposomes: Improved Pharmacokinetic and Biodistribution Profile. Current Drug Delivery 2018, 15, https://doi.org/10.2174/1567201815666181024112252.
30. Khan, S.A.; Asiri, A.M. Green synthesis, characterization and biological evaluation of novel chalcones as anti bacterial agents. Arabian Journal of Chemistry 2017, 10, S2890-S2895, https://doi.org/10.1016/j.arabjc.2013.11.018.
31. Kurt, B.Z.; OztenKandas, N.; Dag, A.; Sonmez, F.; Kucukislamoglu, M. Synthesis and biological evaluation of novel coumarin-chalcone derivatives containing urea moiety as potential anticancer agents. Arabian Journal of Chemistry 2020, 13, 1120-1129, https://doi.org/10.1016/j.arabjc.2017.10.001.
32. Seema, I.H. Chemical and biological potential of chalcones as a source of drug.Ijppr2018, 11,104-118.
33. Baluja, S.; Vakariya, N.; Hirapara, A.Synthesis, phytochemical studies of vanillin chalcones. Scientific research2018, 47, 185-215, http://dx.doi.org/10.15446/rcciquifa.v47n2.73966.
34. Deepika, P.; Maheswari, D.U.; Kumar, P.S.S.Chalcones as Promising Antiproliferative Drug-A Review.Ijrsi2020, 7, 53.
35. Ardiansah, B. Chalcones bearing N, O, and S-heterocycles: Recent notes on their biological significances. Journal of Applied Pharmaceutical Science 2019, 9, 117-129, https://doi.org/10.7324/JAPS.2019.90816.
36. Koudokpon, H.; Armstrong, N.; Dougnon, T.V.; Fah, L.; Hounsa, E.; Bankole, H.S.; Loko, F.; Chabriere, E.; Rolain, J.M. Antibacterial Activity of Chalcone and Dihydrochalcone Compounds from Uvariachamae Roots against Multidrug-Resistant Bacteria. BioMed research international 2018, 2018, https://doi.org/10.1155/2018/1453173.