VITAMIN B1PROMOTED GREEN SYNTHESIS OF BENZOFURAN CHALCONES: PROMISING SCAFFOLDS FOR DRUG DEVELOPMENT IN ANTIMICROBIAL
Keywords:
Benzofuran, chalcones, vitamin B1catalyst, antimicrobial propertyAbstract
Objective: To develop metal free and environmentally benign synthetic method for the synthesis of chalcones bearing benzofuran scaffolds. Materials and Methods:Starting material chloroacetone,anhydrous potassium carbonate, different aromatic aldehydes, ethanol and vitamin B1 of AR grade wereused for synthesis.Various chalcones were synthesized byClaisen-Schmidt condensation.The structure of the synthesized compounds was confirmed by elemental analysis, IR,1H NMR and mass spectra.
Results:In this context we have tried new metal free and environmentally benign synthetic method for synthesis of the pharmaceutically important molecule 1-(4-substituted-1-benzofuran-2-yl) substituted chalcones and its derivatives and it was screened for their antimicrobial activity.Most of the compounds exhibited the good to moderate activity.
Conclusion:Herein we have tried a highly efficient protocol for the synthesis of chalconesa good result with variety of functionalities, a high yield of products, and the recoverability of this catalyst.Vitamin B1 as a catalyst has been developed using green solvent EtOH.
References
1. Eslam RES, Adel HM, Salwa MEH, KamelHS.Synthesisof some benzofuran derivatives containing pyrimidine moiety as potent antimicrobial agents. Iran.J.Pharm.Res. 2018;17(1): 75-86.
2. McCallionGD.Benzofurans: An investigation into natural products, bioactivity and synthesis. Curr. Org. Chem.1999; 3:67–76.
3. Liu J, Jiang F, Jiang X, Zhang W, and Lei F. Synthesis and antimicrobial evaluation of 3-methanone-6-substituted-benzofuran derivatives.Eur.J.Med.Chem.2012;54:879-86.
4. Rajanarendar E, Govardhan RK, Krishna SR, Shireesha B, and Rajam MV. Design,synthesis, antimicrobial,anti-inflammatory, and analgesic activity of novel dihydrobenzofuro[3,2-e]isoxazolo[4,5-b]azepin-5(5aH)-ones.Med.Chem.Res.2013;22:6143-53.
5. M.M. Hawash, D.C. Kahraman, F. Eren, R.C. Atalay, S.N. Baytas.Synthesis and biological evaluation of novel pyrazolic chalcones derivatives as novel hepatocellular carcinoma therapeutics.Eur. J. Med. Chem.2017;129:12-26.
6. BortolottoLF,Barbosa FR, SilvaG,BitencourtTA, Beleboni RO, Beak SJ, MarinsM, FachinAL.Novel 1-(7-ethoxy-1-benzofuran-2-yl) substituted chalcones derivatives: Synthesis, characterization and anticancer activity. Eur.J.Chem. 2017;136:212-22.
7. Kraege S, Stefan K, Juvale K, Ross T, Willmes T, Wiese M .The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2).Eur. J. Med. Chem.2016;117:212–29.
8. GoML,WuX, LiuXL.Chalcones: an update on cytotoxic and chemo protective properties.Curr. Med. Chem. 2005;12: 481-99.
9. Lawrence N., McGownA.The chemistry and biology of antimitotic chalcones and related enonesystems.Curr. Pharm. Des.2005;11(13):1679-93.
10. Sahu NK, Balbhadra SS, Choudhary J,Kohli D.Exploring pharmacological significance of chalcone scaffold: A review.Curr. Med. Chem. 2012;19(2):209-25.
11. ReddyM.V., SuC.R.,ChiouW.F., LiuY.N., ChenR.Y., BastowK.F., LeeK.H., WuT.S. Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents.Bioorg.Med. Chem. 2008;16(15): 7358-70.
12. SharmaA., ChakravartiB.,GuptaM.P., Siddiqui J.A., Konwar R. Synthesis and anti-breast cancer activity of biphenyl based chalcones. Bioorg.Med.Chem. 2010;18(13): 4711-20.
13. SashidharaK.V., KumarA., KumarM., SarkarJ., SinhaS.Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents.Bioorg.Med.Chem.Lett. 2010;20(24):7205-11.
14. SyamS.,Abdelwahab SI.,Al-MamaryMA.Synthesis of chalcones with anticancer activities.Molecules, 2012;17(6):6179-95.
15. Cheng JH,HungCF,YangSC,WangJP, WonSJ,Lin CN, Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2',5'-dialkoxylchalcones as cancer chemopreventive agents.Bioorg.Med.Chem.2008;16(15):7270-76.
16. Bandgar BP, GawandeSS,BodadeRG,TotreJV,Khobragade CN. Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents.Bioorg.Med.Chem.2010;18(3):1364-70.
17. LawrenceNJ, PattersonRP,OoiLL, Cook D,DuckiS.Effects of ?-substitutions on structure and biological activity of anticancer chalcones. Bioorg. Med. Chem. Lett.2006;16:5844-48.
18. DyragerC, Wickstrom M, Friden-Saxin M, FribergA, DahlenK,Wallen J, GullboEA,GrotliM, Luthman K. Inhibitors and promoters of tubulin polymerization: synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents. Bioorg.Med.Chem.2011;19(8):2659-65.
19. l-Meligie S, Taher AT, KamalAM,Design, synthesis and cytotoxic activity of certain novel chalcones analogous compounds.Eur.J.Med.Chem.2017;126:52-60.
20. KelloM, DrutovicD, PilatovaMP, Tischlerova V,PerjesiP, MojzisJ.Chalcone derivatives cause accumulation of colon cancer cells in the G2/M phase and induce apoptosis.Life.Sci.2016;150:32-48.
21. León-González AJ,Acero N, Muñoz-MingarroD,NavarroI, Martín-CorderoC.Chalcones as Promising Lead Compounds on Cancer Therapy.Curr. Med. Chem.2015;22(30):3407-25.
22. HacerB,AhmetD,NeslihanD,Sengul AK. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities .Eur.J.Chem.2009;44(11):4362-66
2. McCallionGD.Benzofurans: An investigation into natural products, bioactivity and synthesis. Curr. Org. Chem.1999; 3:67–76.
3. Liu J, Jiang F, Jiang X, Zhang W, and Lei F. Synthesis and antimicrobial evaluation of 3-methanone-6-substituted-benzofuran derivatives.Eur.J.Med.Chem.2012;54:879-86.
4. Rajanarendar E, Govardhan RK, Krishna SR, Shireesha B, and Rajam MV. Design,synthesis, antimicrobial,anti-inflammatory, and analgesic activity of novel dihydrobenzofuro[3,2-e]isoxazolo[4,5-b]azepin-5(5aH)-ones.Med.Chem.Res.2013;22:6143-53.
5. M.M. Hawash, D.C. Kahraman, F. Eren, R.C. Atalay, S.N. Baytas.Synthesis and biological evaluation of novel pyrazolic chalcones derivatives as novel hepatocellular carcinoma therapeutics.Eur. J. Med. Chem.2017;129:12-26.
6. BortolottoLF,Barbosa FR, SilvaG,BitencourtTA, Beleboni RO, Beak SJ, MarinsM, FachinAL.Novel 1-(7-ethoxy-1-benzofuran-2-yl) substituted chalcones derivatives: Synthesis, characterization and anticancer activity. Eur.J.Chem. 2017;136:212-22.
7. Kraege S, Stefan K, Juvale K, Ross T, Willmes T, Wiese M .The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2).Eur. J. Med. Chem.2016;117:212–29.
8. GoML,WuX, LiuXL.Chalcones: an update on cytotoxic and chemo protective properties.Curr. Med. Chem. 2005;12: 481-99.
9. Lawrence N., McGownA.The chemistry and biology of antimitotic chalcones and related enonesystems.Curr. Pharm. Des.2005;11(13):1679-93.
10. Sahu NK, Balbhadra SS, Choudhary J,Kohli D.Exploring pharmacological significance of chalcone scaffold: A review.Curr. Med. Chem. 2012;19(2):209-25.
11. ReddyM.V., SuC.R.,ChiouW.F., LiuY.N., ChenR.Y., BastowK.F., LeeK.H., WuT.S. Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents.Bioorg.Med. Chem. 2008;16(15): 7358-70.
12. SharmaA., ChakravartiB.,GuptaM.P., Siddiqui J.A., Konwar R. Synthesis and anti-breast cancer activity of biphenyl based chalcones. Bioorg.Med.Chem. 2010;18(13): 4711-20.
13. SashidharaK.V., KumarA., KumarM., SarkarJ., SinhaS.Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents.Bioorg.Med.Chem.Lett. 2010;20(24):7205-11.
14. SyamS.,Abdelwahab SI.,Al-MamaryMA.Synthesis of chalcones with anticancer activities.Molecules, 2012;17(6):6179-95.
15. Cheng JH,HungCF,YangSC,WangJP, WonSJ,Lin CN, Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2',5'-dialkoxylchalcones as cancer chemopreventive agents.Bioorg.Med.Chem.2008;16(15):7270-76.
16. Bandgar BP, GawandeSS,BodadeRG,TotreJV,Khobragade CN. Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents.Bioorg.Med.Chem.2010;18(3):1364-70.
17. LawrenceNJ, PattersonRP,OoiLL, Cook D,DuckiS.Effects of ?-substitutions on structure and biological activity of anticancer chalcones. Bioorg. Med. Chem. Lett.2006;16:5844-48.
18. DyragerC, Wickstrom M, Friden-Saxin M, FribergA, DahlenK,Wallen J, GullboEA,GrotliM, Luthman K. Inhibitors and promoters of tubulin polymerization: synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents. Bioorg.Med.Chem.2011;19(8):2659-65.
19. l-Meligie S, Taher AT, KamalAM,Design, synthesis and cytotoxic activity of certain novel chalcones analogous compounds.Eur.J.Med.Chem.2017;126:52-60.
20. KelloM, DrutovicD, PilatovaMP, Tischlerova V,PerjesiP, MojzisJ.Chalcone derivatives cause accumulation of colon cancer cells in the G2/M phase and induce apoptosis.Life.Sci.2016;150:32-48.
21. León-González AJ,Acero N, Muñoz-MingarroD,NavarroI, Martín-CorderoC.Chalcones as Promising Lead Compounds on Cancer Therapy.Curr. Med. Chem.2015;22(30):3407-25.
22. HacerB,AhmetD,NeslihanD,Sengul AK. Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities .Eur.J.Chem.2009;44(11):4362-66
Published
31-05-2020
How to Cite
VENKAT S., S. (2020). VITAMIN B1PROMOTED GREEN SYNTHESIS OF BENZOFURAN CHALCONES: PROMISING SCAFFOLDS FOR DRUG DEVELOPMENT IN ANTIMICROBIAL. Innovare Journal of Sciences, 8(7), 45–47. Retrieved from https://journals.innovareacademics.in/index.php/ijs/article/view/38526
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