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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

40% aq. HF Catalyzed Three-Component Synthesis of Novel Indeno[1, 2-b][1,8]naphthyridin-6(11H)-one Derivatives and their Antimicrobial Activity

Author(s): Srinu Bhoomandla, Phani Raja Kanuparthy*, Rambabu Gundla and Ramana Reddy Bobbala

Volume 18, Issue 1, 2021

Published on: 10 February, 2020

Page: [13 - 21] Pages: 9

DOI: 10.2174/1570178617666200210112843

Price: $65

Abstract

A three-component synthesis of novel 5-phenyl-2-(thiophen-2-yl)-4-(trifluoromethyl)-5Hindeno [1,2-b] [1,8] naphthyridin-6(11H)-one derivatives (4a-n) was prepared using 6-phenyl/ (thiophen- 2-yl)-4-(trifluoromethyl)pyridin-2-amine, 1H-indene-1,3(2H)-dione, and aryl aldehyde using 40% aq. HF with good yield. All the synthesized compounds were screened against Gram-positive and Gram-negative bacterial strains and different Candida strains by the well diffusion method. Compounds 4c, 4f, and 4g showed promising activity on Bacillus subtilis strain and compounds 4c and 4g showed promising activity towards Candida albicans strains.

Keywords: Naphthyridine, trifluoromethyl pyridine, 40% aq. HF, michael addition, antimicrobial activity, molecular docking studies.

Graphical Abstract

[1]
(a)Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. Engl., 2000, 39(18), 3168-3210.
[http://dx.doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U] [PMID: 11028061]
(b)Nair, V.; Rajesh, C.; Vinod, A.U.; Bindu, S.; Sreekanth, A.R.; Mathen, J.S.; Balagopal, L. Acc. Chem. Res., 2003, 36(12), 899-907.
[http://dx.doi.org/10.1021/ar020258p] [PMID: 14674781]
[2]
Litvinov, V.P.; Roman, S.V.; Dyachenko, V.D. Naphthyridines. Russ. Chem. Rev., 2000, 69, 201-220.
[http://dx.doi.org/10.1070/RC2000v069n03ABEH000553]
[3]
Ramesh, D.; Sreenivasulu, B.; Indian, J. Het. Chem., 2006, 15, 363-365.
[4]
Barbara, B.; Teresa, Z. ARKIVOC, 2001, 6, 77-84.
[5]
Massari, S.; Daelemans, D.; Barreca, M.L.A.; Knezevich, A.; Sabatini, S.; Cecchetti, V.; Marcello, A.; Pannecouque, C.; Tabarrini, O. J. Med. Chem., 2010, 53(2), 641-648.
[http://dx.doi.org/10.1021/jm901211d] [PMID: 19958026]
[6]
Fadda, A.A.; El-Defrawy, A.M.; El-Habiby, S.A. Am. J. Org. Chem, 2012, 2, 87-96.
[http://dx.doi.org/10.5923/j.ajoc.20120204.03]
[7]
Roma, G.; Grossi, G.; Di Braccio, M.; Piras, D.; Ballabeni, V.; Tognolini, M.; Bertoni, S.; Barocelli, E. Eur. J. Med. Chem., 2008, 43(8), 1665-1680.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.010] [PMID: 18045747]
[8]
Olepu, S.; Suryadevara, P.K.; Rivas, K.; Yokoyama, K.; Verlinde, C.L.; Chakrabarti, D.; Van Voorhis, W.C.; Gelb, M.H. Bioorg. Med. Chem. Lett., 2008, 18(2), 494-497.
[http://dx.doi.org/10.1016/j.bmcl.2007.11.104] [PMID: 18077162]
[9]
Laxminarayana, E.; Karunakar, T.; Shankar, S.S.; Chary, M.T. Adv. Drug Deliv. Rev., 2012, 2, 6-11.
[10]
Quintela, J.M.; Peinador, C.; González, L.; Iglesias, R.; Paramá, A.; Alvarez, F.; Sanmartín, M.L.; Riguera, R. Eur. J. Med. Chem., 2003, 38(3), 265-275.
[http://dx.doi.org/10.1016/S0223-5234(03)00032-1] [PMID: 12667693]
[11]
Aboul-Fadl, T.; Bin-Jubair, F.A.S.; Aboul-Wafa, O. Eur. J. Med. Chem., 2010, 45(10), 4578-4586.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.020] [PMID: 20696500]
[12]
Ferrarini, P.L.; Mori, C.; Badawneh, M.; Franconi, F.; Manera, C.; Miceli, M.; Saccomanni, G. Farmaco, 2000, 55(9-10), 603-610.
[http://dx.doi.org/10.1016/S0014-827X(00)00085-9 ] [PMID: 11152241]
[13]
Kren, V.; Rezanka, T. FEMS Microbiol. Rev., 2008, 32(5), 858-889.
[http://dx.doi.org/10.1111/j.1574-6976.2008.00124.x PMID: 18647177]
[14]
Kren, V.; Martínková, L. Curr. Med. Chem., 2001, 8(11), 1303-1328.
[http://dx.doi.org/10.2174/0929867013372193] [PMID: 11562268]
[15]
Yale, H.L. J. Med. Pharm. Chem., 1959, 1(2), 121-133.
[http://dx.doi.org/10.1021/jm50003a001] [PMID: 13665284]
[16]
Appel, W.K.; Siegemund, G.; Stöbbe, M. J. Fluor. Chem., 1991, 54, 92.
[http://dx.doi.org/10.1016/S0022-1139(00)83602-7]
[17]
(a)Kappe, C.O. Eur. J. Med. Chem., 2000, 35(12), 1043-1052.
[http://dx.doi.org/10.1016/S0223-5234(00)01189-2] [PMID: 11248403]
(b)Kappe, C.O. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
(c)McDonald, A.I.; Overman, L.E. J. Org. Chem., 1999, 64(5), 1520-1528.
[http://dx.doi.org/10.1021/jo981972g] [PMID: 11674214]
(d)Biginelli, P. Eur. J. Inorg. Chem., 1891, 24, 1317-1319.
(e)Biginelli, P. Eur. J. Inorg. Chem., 1891, 24, 2962-2967.
[18]
Mondal, J.; Sen, T.; Bhaumik, A. Dalton Trans., 2012, 41(20), 6173-6181.
[http://dx.doi.org/10.1039/c2dt30106g] [PMID: 22475989]
[19]
Parasuraman, K.; Aswar, S.A.; Muskawar, P.N.; Bhagat, P.R.; Senthil Kumar, S. J. Organomet. Chem., 2013, 723, 154-162.
[http://dx.doi.org/10.1016/j.jorganchem.2012.06.022]
[20]
Lal, J.; Sharma, M.; Guptab, S.; Parashara, P.; Sahua, P.; Agarwala, D.D. J. Mol. Catal. Chem., 2012, 352, 31-37.
[http://dx.doi.org/10.1016/j.molcata.2011.09.009]
[21]
Xu, F.; Huang, D.; Lin, X.; Wang, Y. Org. Biomol. Chem., 2012, 10(22), 4467-4470.
[http://dx.doi.org/10.1039/c2ob25663k] [PMID: 22565820]
[22]
Saha, S.; Moorthy, J.N. J. Org. Chem., 2011, 76(2), 396-402.
[http://dx.doi.org/10.1021/jo101717m] [PMID: 21192642]
[23]
Konkala, K.; Sabbavarapu, K.N.M.; Katla, R.; Durga, N.Y.V.; Vijai Kumar Reddy, T.; Prabhavathi Devi, B.L.A.; Prasad, R.B.N. Tetrahedron Lett., 2012, 53, 1968.
[http://dx.doi.org/10.1016/j.tetlet.2012.02.018]
[24]
Shen, Z.L.; Xu, X.P.; Ji, S.J. J. Org. Chem., 2010, 75(4), 1162-1167.
[http://dx.doi.org/10.1021/jo902394y] [PMID: 20085235]
[25]
Fu, L.; Lin, W.; Hu, M.H.; Liu, X.C.; Huang, Z.B.; Shi, D.Q. ACS Comb. Sci., 2014, 16(5), 238-243.
[http://dx.doi.org/10.1021/co4001524] [PMID: 24669887]
[26]
Mohammad, B.; Nasri, S.J. Het. Chem, 2018, 55, 650-659.
[http://dx.doi.org/10.1002/jhet.3083]
[27]
Makhanya, T.R.; Gengan, R.M.; Pandian, P.; Chuturgoon, A.A.; Tiloke, Ch.; Atar, A.J. Het. Chem, 2018, 55, 1193-1204.
[http://dx.doi.org/10.1002/jhet.3153]
[28]
Ramakrishna, S.; Srinivas Reddy, M.; Nagaraju, D.J. Het. Chem, 2018, 55, 1579-1588.
[http://dx.doi.org/10.1002/jhet.3191]
[29]
Santhosh Kumar, G.; Jitender Dev, G.; Ravi Kumar, N.; Krishna Swaroop, D.; Poorna Chandra, Y.; Ganesh Kumar, C.; Narsaiah, B. Chem. Pharm. Bull. (Tokyo), 2015, 63(8), 584-590.
[http://dx.doi.org/10.1248/cpb.c15-00219] [PMID: 26235166]
[30]
Amsterdam, D. Antibiotics in Laboratory Medicine, 4th ed; Loman, V., Ed.; Williams and Wilkins: Baltimore, MD, 1996, p. 52.

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