SYNTHESIS, ANTIMICROBIAL, ANTIOXIDANT AND DOCKING STUDIES OF (3-METHOXY-5-NITROBENZOFURAN-2-YL)(PHENYL)METHANONE DERIVATIVES.SYNTHESIS, ANTIMICROBIAL, ANTIOXIDANT AND DOCKING STUDY OF (3-ALKOXY-5-NITROBENZOFURAN-2-YL) (PHENYL) METHANONE DERIVATIVES

  • S. K. Rashmi Jain University
  • T. H. Suresha Kumara Jain University
  • C. Sandeep Post Graduate department Of Chemistry Acharya Institute Of Graduate Studies (Affiliated to Bangalore University) Soladevanahalli, Bangalore 560090.
  • G. Nagendrappa Jain University
  • H. B. V. Sowmya Jain University
  • P. S. Sujan Ganapathy Jain University

Abstract

Objective: Synthesis, antimicrobial, antioxidant and docking studies of (3-methoxy-5-nitrobenzofuran-2-yl)(phenyl)methanone derivatives (2a-j).

Methods: The products 2a-j, were obtained from different (3-hydroxy-5-nitrobenzofuran-2-yl)(phenyl)methanonesrefand alkyl bromides in the presence of K2CO3 in DMF at room temperature. Afterwards, characterised through 1H-NMR, [13]C-NMR, ESI-LCMS and elemental analyses. Finally, subjected them for antimicrobial and antioxidant studies through agar well diffusion technique and docking interaction studies through automated docking technique.

Results: From the current procedure, the compound 2a has showed the highest antibacterial activity and 2j showed lowest antibacterial activity. None of these (2a-j) have showed antifungal activity. The compound 2d has shown highest free radical scavenging activity and 2e has shown least activity. The biological properties of the synthesised compounds (2a-j) were further supported by docking studies.

Conclusion: Successfully synthesised and characterized ten individually novel (3-alkoxy-5-nitrobenzofuran-2-yl)(phenyl)methanone derivatives (2a-j) in one pot procedure and studied antimicrobial, antioxidant and docking properties. Perhaps the present work provides an evidence for the preparation, antimicrobial and antioxidant properties of the novel benzofuran derivatives.

 

Keywords: (3-Alkoxy-5-nitrobenzofuran-2-yl)(phenyl) methanone, (3-hydroxy-5-nitrobenzofuran-2-yl)(phenyl) methanones, Antimicrobial activity, Antioxidant activity, Molecular docking studies

Downloads

Download data is not yet available.

Author Biography

C. Sandeep, Post Graduate department Of Chemistry Acharya Institute Of Graduate Studies (Affiliated to Bangalore University) Soladevanahalli, Bangalore 560090.
Post Graduate department of chemistry

References

1. DA Horton, GT Bourne, ML Smythe. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 2003;103:893-930.
2. SS Palimkar, VS More, KV Srinivasan. Ultrasound promoted copper-, ligand-and amine-free synthesis of benzo[b]furans/nitro benzo[b]furans via Sonogashiracoupling-5-endo-dig-cyclization. Ultrason Sonochem2008;15:853-62.
3. B Gerard, CJ Pelletier, JA Porco. Enantioselective synthesis of the complex rocaglate (−)-Silvestro. Angew Chem Int Ed 2007;46:7831-4.
4. F Marion, DE Williams, BO Patrick, I Hollander, R Mallon, SC Kim, et al. Anderson, Liphagal, a Selective inhibitor of PI3 kinase alpha isolated from the sponge akacoralliphaga: structure elucidation and biomimetic synthesis. Org Lett 2006;8:321-4.
5. KS Yeung. Furans and Benzofurans. Top Heterocycl Chem 2012;29:47-76.
6. G Mehta, NS Likhite, CSA Kumar. A concise synthesis of the bioactive meroterpenoid natural product (±)-liphagal, a potent PI3K inhibitor. Tetrahedron Lett 2009;50:5260-2.
7. D Magometschnigg, J Bonelli, G Hitzenberger, G Kaik, A Korn. Decrease of peripheral resistance after acute intravenous application of a new beta-receptor blocking agents, bufuralol HCl. Int J Clin Pharmacol Biopharm 1978;16:54-8.
8. D Magometschnigg, J Bonelli, G Kaik, H Rameis, Hemodynamic changes in hypertensive patients at rest and during physical exercise before and after acute i. v. administration of bufuralol-HCl or propranolol,Int. J. Clin. Pharmacol. Biopharm. 17(1979) 334-340.
9. G. A. Fothergill, J. M. Osbond, J. C. Wickens,Bufuralol, a new beta-adrenoceptor blocking agent. Part 1:synthesis and structure-activity studies in a series of benzofuran-2-ethanolamines,Arzneim.-Forsch. Drug Res. 27(1977) 978-981.
10. D. N. Li, P. M. Pritchard, S. P. Hanlon, B. Burchell, C. R. Wolf, T. Friedberg,Competition between cytochrome P-450 isozymes for NADPH-cytochrome P-450 oxidoreductase affects drug metabolism,J. Pharmacol. Exp. Ther. 289(1999) 661-667.
11. Z. Marek, T. K. Agnieszka, P. K. Andrzej, C. Aldona, Asymmetric synthesis of (S)-bufuralol and a propafenone analogue,Tetrahedron: Asymmetry14(2003)1659-1664.
12. S. Kim, A. A Salim, S. M. Swanson, A. D. Kinghorn, Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy. Anticancer Agents, Med. Chem.6(2006) 319-345.
13. R. Whomsley, E. Fernandez, P. J. Nicholls, H. J. Smith, P. Lombardi, V. Pestellini, Substituted 1-[benzofuran-2-yl)-pHenylmethyl]-imidazoles as potent inhibitors of aromatase In vitro and in female rats in vivo, J. Steroid Biochem. Mol. Biol. 44(1933) 675-676.
14. Hayakawa R Shioya, T Agatsuma, H Furukawa, S Naruto, Y Sugano. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents. Bioorg Med Chem Lett 2004;14:455-8.
15. ZZ Zhou, YH Deng, ZH Jiang, WH Chen. Microwave-Assisted dieckmann reaction: efficient one-step synthesis of 2-Aroylbenzofuran-3-ols. Adv Synth Catal 2010;352:1909-13.
16. SG Patil, VV Bhadke, RR Bagul. Synthesis of 2-Aroylbenzofuran-3-ols using basic ionic liquid [bmIm] OH. J Chem Pharm Res 2010;4:2832-5.
17. ZZ Zhou, M Zou, J Zhou, CQ Zhou, YH Deng, MH Chen, et al. Liu, Synthesis, cytotoxicities and DNA-binding affinities of benzofuran-3-ols and their fused analogs. Chem Pharm Bull 2011;59:1057-61.
18. F Gatta, G Settimj. Reaction of 2-acyl-3-aminobenzofurans with hydrazines. J Heterocycl Chem 1984;21:937-43.
19. WA Moshe R, PM Serridge, DW Lipp. Reactions of 2-acyl-3(2H)-benzofuranones with hydrazines and diamines. J Org Chem 1971;37:2402-5.
20. HA Pershadsingh, D ELevy. Patent WO 2000000194 A1. Chem Abstr 2000;132:73666.
21. M Gerard, L Caroline, K Micheline. Patent FR 2862646 A1. Chem Abstr 2005;143:7588.
22. E Martin, B Felix, S Alessandro, R Subho, S Goutam, SK Kumar, et al. Patent WO 2005061476 A2. Chem Abstr 2005;143:115430.
b) SK Rashmi, TH Suresha kumara, Gopalpur Nagendrappa, HBV Sowmya, Sunil More. Synthetic Communications 2013;44:331–9.
23. PS Sujan Ganapathy, HV Sudeep, S PadmalathaRai, YL Ramachandra. Screening of crude extracts of holarrhenaantidysenterica wall. Against clinically important pathogenic strains. Med Aromatic Plant Sci Biotech 2008;2:68-71.
24. CH Collins, PM Lyne, JM Grange. Microbiological Methods (6th Edn), Butterworhs Co. Ltd, London; 1989. p. 410.
25. MS Ali-Shtayeh, RM Yaghmour, YR Faidi, K Salem, MA Al-Nuri. Antimicrobial activity of 20 plants used in folkloric medicine in the Plastenian area. J Ethnopharmacol 1998;60:265-71.
26. RK Pundir, P Jain. Antifungal activity of twenty two ethanolic plant extracts against food-associated fungi. J Pharm Res 2010;3:506-10.
27. Y Okada, M Okada. Scavenging effect of soluble proteins in broad beans on free radicals and active oxygen species. J Agric Food Chem 1998;46:401-6.
28. GC Yen, PD Duh. Scavenging effect of methanolic extracts of peanut hulls on free radical and active-oxygen species. J Agric Food Chem 1994;42:629-32.
29. K Ghose, GM Crippen. Atomic physicochemical parameters for threedimensional-structure-directed quantitative structure– activity relationships. 2. Modeling dispersive and hydrophobic interactions. J Chem Inf Comput Sci 1987;27:21–35.
30. TA Binkowski, S Naghibzadeg, J Liang. CASTp computed atlas of surface topography of proteins. Nucleic Acid Res 2003;31:3352–5.
31. J Gasteiger, M Marsili. Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron 1980;36:3219–88.
32. SM Vidya, V Krishna, BK Manjunatha, KP Rajesh, BR Bharath, H Manjunatha. Antibacterial and molecular docking studies of entagenic acid, a bioactive principle from seed kernel of Entadapursaetha DC. Med Chem Res 2012;21:1016-22.
Statistics
384 Views | 834 Downloads
How to Cite
Rashmi, S. K., T. H. S. Kumara, C. Sandeep, G. Nagendrappa, H. B. V. Sowmya, and P. S. S. Ganapathy. “SYNTHESIS, ANTIMICROBIAL, ANTIOXIDANT AND DOCKING STUDIES OF (3-METHOXY-5-NITROBENZOFURAN-2-YL)(PHENYL)METHANONE DERIVATIVES.SYNTHESIS, ANTIMICROBIAL, ANTIOXIDANT AND DOCKING STUDY OF (3-ALKOXY-5-NITROBENZOFURAN-2-YL) (PHENYL) METHANONE DERIVATIVES”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 7, no. 2, Dec. 2014, pp. 493-7, https://innovareacademics.in/journals/index.php/ijpps/article/view/4041.
Section
Original Article(s)