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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Chromene, Quinoline Hybrids as Potential Anti-Cancer Agents: A Novel and Distinct Approach for the Synthesis of Quinoline Derivatives

Author(s): Rizuana Sultana and Ravinder Reddy Tippanna*

Volume 18, Issue 4, 2021

Published on: 22 January, 2020

Page: [265 - 272] Pages: 8

DOI: 10.2174/1570178617666200122095829

Price: $65

Abstract

A series of novel quinoline derivatives (6-phenyl-6H-chromeno[4,3-b]quinoline) have been prepared by using 4-chloro-2-phenyl-2H-chromene-3-carbaldehyde and various substituted isocyanides as starting materials in the presence of HClO4-SiO2 and Methanol. We screened eighteen compounds of this novel series (6a-r) in six different cancer cell lines (A549 (lung cancer cells), DU145 (prostate cancer cells), PC3 (prostate cancer cells), MCF7 (lung cancer cells), HT 29, HCT 116 (colon cancer cells). Most of the compounds showed anti-cancer activity and compound 6b showed good cytotoxicity IC50 = 2.61±0.34 μM against colon cancer on HT29 cell line among all. The key property of cell migration was observed while treatment cells with 6b. Apoptosis in HT29 cells confirmed by annexin V staining, acridine orange/ethidium bromide (AO/EB), DAPI, induced by 6b. This method is operationally simple and works with a diverse range of substrates. These results indicate the anticancer potential of these series and warrants future investigations for further anticancer drug development.

Keywords: Quinolines, Chromeno-3-carbaldehyde, Silica-supported perchloric acid, Isocyanides, apoptosis, Anti-cancer agents.

Graphical Abstract

[1]
Monica, R.; Vlado, D.; Bridget, K.W.; Paul, A.C. Nat. Chem. Biol., 2013, 9, 232-240.
[http://dx.doi.org/10.1038/nchembio.1199] [PMID: 23508189]
[2]
(a)Musiol, R. Expert Opin. Drug Discov., 2017, 12(6), 583-597.,
[http://dx.doi.org/10.1080/17460441.2017.1319357] [PMID: 28399679]
(b)Solomon, V.R.; Lee, H. Curr. Med. Chem., 2011, 18(10), 1488-1508.,
[http://dx.doi.org/10.2174/092986711795328382] [PMID: 21428893]
(c)Gaspar, A.; Matos, M.J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev., 2014, 114(9), 4960-4992.,
[http://dx.doi.org/10.1021/cr400265z] [PMID: 24555663]
(d)Joana, R.; Alexandra, G.; Nuno, M.; Fernanda, B. J. Med. Chem., 2017,60, 7941-7957.,
[http://dx.doi.org/10.1021/acs.jmedchem.6b01720] [PMID: 28537720]
(e)Keri, R.S.; Budagumpi, S.; Pai, R.K.; Balakrishna, R.G. Eur. J. Med. Chem., 2014, 78, 340-374.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.047] [PMID: 24691058]
[3]
(a)Osiadacz, J.; Kaczmarek, L.; Opolski, A.; Wietrzyk, J.; Marcinkowska, E.; Biernacka, K.; Radzikowski, C.; Jon, M.; Peczyńska-Czoch, W. Anticancer Res., 1999, 19(4B), 3333-3342.
[PMID: 10652630]
(b)Martirosyan, A.R.; Rahim-Bata, R.; Freeman, A.B.; Clarke, C.D.; Howard, R.L.; Strobl, J.S. Biochem. Pharmacol.,2004, 68(9), 1729-1738..
[http://dx.doi.org/10.1016/j.bcp.2004.05.003] [PMID: 15450938]
(c)Tsotinis, A.; Vlachou, M.; Zouroudis, S.; Jeney, A.; Timar, F.; Thruston, D.E.; Roussakis, C. Lett. Drug Des. Discov., 2005, 2,189-192.,
[http://dx.doi.org/10.2174/1570180053765075]
(d)Rao, Y.J.; Reddy, P.E.; Thirupathi, G.E.; Yadaiah, G.; Sowjanya, M.; Hemasri, Y. Russ. J. Gen. Chem., 2016, 86, 1730-1734.
[http://dx.doi.org/10.1134/S1070363216070318]
[4]
(a)Michael, J.P. Quinoline, quinazoline and acridone alkaloids.Nat.Prod. Rep., 2005, 22(5), 627-646.,
[http://dx.doi.org/10.1039/b413750g] [PMID: 16193160]
(b)Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep., 2007, 24(1), 223-246.
[http://dx.doi.org/10.1039/b509528j] [PMID: 17268614]
[5]
(a)Miller, D.; Wang, S.; Reid, J.; Xie, W.; Gauvin, B.; Kelley, M.; Sarup, J.; Sawutz, D.G.; Miski, M.; Dolle, R.E.; Faltynek, C.R. Drug Dev.Res., 1995.34, 344-352.
[http://dx.doi.org/10.1002/ddr.430340406]
(b)Vangapandu, S.; Jain, M.; Jain, R.; Kaur, S.; Singh, P.P. Ring-substituted quinolines as potential anti-tuberculosis agents.Bioorg. Med. Chem., 2004,12(10), 2501-2508.,
[http://dx.doi.org/10.1016/j.bmc.2004.03.045] [PMID: 15110831]
(c)Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J.T. Synthesis, anticonvulsant and antihypertensive activities of 8-substituted quinoline derivatives. Biol. Pharm. Bull., 2004, 27(10), 1683-1687.,
[http://dx.doi.org/10.1248/bpb.27.1683] [PMID: 15467220]
(d)Martyanov, I.V.; Zakharova, O.D.; Sottofattori, E.; Pyshnyi, D.V.; Yurchenko, E.Y.; Babbi, P.; Mazzei, M.; Balbi, A.; Andreola, M.L.; Litvak, S.; Tarrago-Litvak, L.; Nevinsky, G.A. Antisense Nucleic Acid Drug Dev., 1999, 9(5), 473-480.,
[http://dx.doi.org/10.1089/oli.1.1999.9.473] [PMID: 10555155]
(e)Camps, P.; Gómez, E.; Muñoz-Torrero, D.; Badia, A.; Vivas, N.M.; Barril, X.; Orozco, M.; Luque, F.J. J. Med. Chem., 2001,44(26), 4733-4736..
[http://dx.doi.org/10.1021/jm010949b] [PMID: 11741490]
(f)Benhamú, B.; Martín-Fontecha, M.; Vázquez-Villa, H.; Pardo, L. López, Rodríguez, M. L. J. Med. Chem., 2014, 57, 7160-7181.
[PMID: 24850589]
(g)Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B.M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J.C. J. Med. Chem., 1995, 38(14), 2692-2704.
[http://dx.doi.org/10.1021/jm00014a021] [PMID: 7629808]
[6]
(a)Hoemann, M.Z.; Kumaravel, G.; Xie, R.L.; Rossi, R.F.; Meyer, S.; Sidhu, A.; Cuny, G.D.; Hauske, J.R. Bioorg. Med. Chem. Lett.,2000, 10(23), 2675-2678.,
[http://dx.doi.org/10.1016/S0960-894X(00)00542-4] [PMID: 11128649]
(b)Costantino, L.; Rastelli, G.; Gamberini, M.C.; Vinson, J.A.; Bose, P.; Iannone, A.; Staffieri, M.; Antolini, L.; Del Corso, A.; Mura, U.; Albasini, A. J. Med. Chem., 1999, 42(11),1881-1893.,
[http://dx.doi.org/10.1021/jm980441h] [PMID: 10354396]
(c)Ellis, G.P. Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones; John Wiley & Sons, Inc; New York, 1977, 31, pp. 495-555;
[7]
(a)Reddy, T.R.; Sreenivas, P.; Reddy, K.M. Heterocyclic letters, 2013, 3(4), 437-442.
(b)Reddy, K.M.; Reddy, T.R.; Raju, R.K. Phosphourus, Sulfur., 2010, 185(2), 313-318.
[http://dx.doi.org/10.1080/10426500902787724]
[8]
(a)Moorty, S.R.; Sundaramurthy, V.; Subba Rao, N.V. Indian J. Chem., 1973, 11, 854-856.
(b)Venkati, M.; Satyanarayana, R.S.; Swamy, G.Y.S.K.; Ravikumar, K.; Krupadanam, G.L.D. Arkivok, 2012, 355-364.
[9]
(a)Baker, W. J. Chem. Soc., 1933, 51, 1381-1389.,
[http://dx.doi.org/10.1039/jr9330001381]
(b)Baker, W. J. Chem.Soc., 1934, 52, 1953-1954.,
[http://dx.doi.org/10.1039/jr9340001953]
(c)Mahal, H.S.; Venkataraman, K. J. Chem. Soc., 1934, 53, 1767-1769.,
[http://dx.doi.org/10.1039/jr9340001767]
(d)Bhalla, D.C.; Mahal, H.S.; Venkataraman, K. J. Chem. Soc., 1935, 868-870.
[http://dx.doi.org/10.1039/jr9350000868, Joule, J.A.; Mills, K. Heterocyclic Chemistry, 5th ed; John Wiley & Sons: United Kingdom, 2010. ]
[10]
Veerababurao, K.; Chunchi, L.; Chun-Wei, K.; Hulin, F.; Ching-Fa, Y. Tetrahedron, 2012, 68, 1321-1329.
[http://dx.doi.org/10.1016/j.tet.2011.11.022]
[11]
Shrivastava, S.; Kulkarni, P.; Thummuri, D.; Jeengar, M.K.; Naidu, V.G.M.; Alvala, M.; Redddy, G.B.; Ramakrishna, S. Apoptosis, 2014, 19(7), 1148-1164.
[http://dx.doi.org/10.1007/s10495-014-0991-2] [PMID: 24729100]
[12]
Hahm, E.R.; Moura, M.B.; Kelley, E.E.; Van Houten, B.; Shiva, S.; Singh, S.V. PLoS One, 2011, 6(8)e23354
[http://dx.doi.org/10.1371/journal.pone.0023354] [PMID: 21853114]
[13]
Kennedy, S.G.; Kandel, E.S.; Cross, T.K.; Hay, N. Mol. Cell. Biol., 1999, 19(8), 5800-5810.
[http://dx.doi.org/10.1128/MCB.19.8.5800] [PMID: 10409766]
[14]
Browne, L.J.; Gude, C.; Rodriguez, H.; Steele, R.E.; Bhatnager, A. J. Med. Chem., 1991, 34(2), 725-736.
[http://dx.doi.org/10.1021/jm00106a038] [PMID: 1825337]
[15]
Reddy, T.S.; Kulhari, H.; Reddy, V.G.; Rao, A.V.S.; Bansal, V.; Kamal, A.; Shukla, R. Org. Biomol. Chem., 2015, 13, 10136-10149.
[http://dx.doi.org/10.1039/C5OB00842E] [PMID: 26346902]

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