Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study

Venkata Swamy Tangeti; D. Vasundhara; M. Naresh Kumar; Himabindu Mylapalli; Kaja Srinivas Pavan Kumar

doi:10.14233/ajchem.2017.20209

Issue

Vol. 29 No. 3 (2017): Vol 29 Issue 3

Issue Published : December 30, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study

https://doi.org/10.14233/ajchem.2017.20209

Venkata Swamy Tangeti

Department of Chemistry, Raghu Engineering College, Visakhapatnam-531 162, India

D. Vasundhara

Department of Chemistry, Raghu Institute of Technology, Visakhapatnam-531 162, India

M. Naresh Kumar

Department of Chemistry, Raghu Institute of Technology, Visakhapatnam-531 162, India

Himabindu Mylapalli

Department of Chemistry, Raghu Engineering College, Visakhapatnam-531 162, India

Kaja Srinivas Pavan Kumar

GVK Biosciences Pvt. Ltd., Nacharam, Hyderabad-500 076, India

Corresponding Author(s) : Venkata Swamy Tangeti

swamychempcu8@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 3 (2017): Vol 29 Issue 3
Article Published : December 30, 2016

Abstract

A series of novel C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-triones were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial and anticancer activities and structure and activity relationship (SAR) was investigated. Structure and activity relationship studies revealed that the compounds 6p, 6q, 6s, 6t were found to be more active in antimicrobial screening. Antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-trione with methoxy group substitution at ring A and B were selected for further structure activity relationship. Among the derivatives, (2S,3S)-propyl-4-acetyl-5-(7,9-dimethoxy-2,5,10-trioxo-5,10-dihydro-2H-benzo[g]chromen-3-yl)-3-(3,5-dimethoxyphenyl)-2,3-dihydrofuran-2-carboxylate (6t) showed most potent cytotoxic activity against all the three cancer cell lines. Toxicity studies revealed that dihydrofuran substituted 1H-benzo[g] chromene-2,5,10-triones (6a-t) are specifically target the cancer cell lines.

Keywords

Multicomponent Antiprolifirative activity Dihydrofuran substituted benzochromene trione Antimicrobial

Tangeti, V. S., Vasundhara, D., Kumar, M. N., Mylapalli, H., & Pavan Kumar, K. S. (2016). Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study. Asian Journal of Chemistry, 29(3), 503–511. https://doi.org/10.14233/ajchem.2017.20209

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References

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References

A.J.M. da Silva, C.D. Buarque, F.V. Brito, L. Aurelian, L.F. Macedo, L.H. Malkas, R.J. Hickey, D.V.S. Lopes, F. Noël, Y.L.B. Murakami, N.M.V Silva, P.A. Melo, R.R.B Caruso, N.G. Castro and P.R.R Costa, Bioorg. Med. Chem., 10, 2731 (2002).

B.G. Qabaja and G.B. Jones, J. Org. Chem., 65, 7187 (2000).

M. Rueping, E. Sugiono and E. Merino, Angew. Chem. Int. Ed., 47, 3046 (2008).

P.M. Brown, V. Krishnamoorthy, J.W. Mathieson and R.H. Thomson, J. Chem. Soc. C, 109 (1970).

M.A. Keniry and G.A. Poulton, Magn. Reson. Chem., 29, 46 (1991).

I.E. Soria-Mercado, A. Prieto-Davo, P.R. Jensen and W. Fenical, J. Nat. Prod., 68, 904 (2005).

M.P.S. Ishar, G. Singh, S. Singh, K.K. Sreenivasan and G. Singh, Bioorg. Med. Chem. Lett., 16, 1366 (2006).

J.Y. Goujon, F. Zammattio, S. Pagnoncelli, Y. Boursereau and B. Kirschleger, Synlett, 322 (2002).

B. Kesteleyn, N. De Kimpe and L. Van Puyvelde, J. Org. Chem., 64, 1173 (1999).

S. Claessens, G. Verniest, J. Jacobs, E. Van Hende, P. Habonimana, T. Nguyen Van, L. Van Puyvelde and N. De Kimpe, Synlett, 829 (2007).

B. Kesteleyn, N. De Kimpe and L. van Puyvelde, Synthesis, 1881 (1999).

T.B. Machado, A.V. Pinto, M.C.F.R. Pinto, I.C.R. Leal, M.G. Silva, A.C.F. Amaral, R.M. Kuster and K.R. Netto-dos Santos, Int. J. Antimicrob. Agents, 21, 279 (2003).

S.L. Schreiber, Science, 287, 1964 (2000).

L.A. Thompson, Curr. Opin. Chem. Biol., 4, 324 (2000).

B.M. Trost, Angew. Chem. Int. Ed. Engl., 34, 259 (1995).

L.F. Tietze, Chem. Rev., 96, 115 (1996).

I. Ugi, Pure Appl. Chem., 73, 187 (2001).

A. Dömling, Chem. Rev., 106, 17 (2006).

D.J. Ramon and M. Yus, Angew. Chem. Int. Ed., 44, 1602 (2005).

A. Dömling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000).

J.D. Sunderhaus, C. Dockendorff and S.F. Martin, Org. Lett., 9, 4223 (2007).

F. Liéby-Muller, T. Constantieux and J. Rodriguez, J. Am. Chem. Soc., 127, 17176 (2005).

C. Haurena, E. Le Gall, S. Sengmany, T. Martens and M. Troupel, J. Org. Chem., 75, 2645 (2010).

B. Willy and T.J.J. Muller, Eur. J. Org. Chem., 4157 (2008).

V.S. Tangeti, G.V. Siva Prasad, J. Panda and K.R. Varma, Synth. Commun., 46, 878 (2016).

H.S.P. Rao and V.S. Tangeti, J. Chem. Sci., 125, 777 (2013).

H.S.P. Rao, V.S. Tangeti and L. Adigopula, Res. Chem. Intermed., 42, 7285 (2016).

V.S. Tangeti, R. Varma K, G.V. Siva Prasad and K.V.V.V. Satyanarayana, Synth. Commun., 46, 613 (2016).

J.C. Duff and E.J. Bills, J. Chem. Soc., 1987 (1932).

J.B. Harborne and H. Baxter, The Handbook of Natural Flavonoids, John Wiley & Sons, Chichester, UK (1999).

Issue

Vol. 29 No. 3 (2017): Vol 29 Issue 3

Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study

Corresponding Author(s) : Venkata Swamy Tangeti

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