European Journal of Chemistry

Synthesis, characterization and in vitro biological evaluation of some new diarylsulfonylurea-chalcone hybrids as potential 5-lipoxygenase inhibitors

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Published: Dec 31, 2013
DOI: https://doi.org/10.5155/eurjchem.4.4.396-401.878
Keywords:
Chalcone, 5-Lipoxygenase, Diarylsulfonylurea, Abietic acid (LI01020), Claisen-Schmidt condensation, Diarylsulfonylurea-chalcone hybrid
Section
Research Article
Issue
Vol. 4 No. 4 (2013): December 2013
Dates
Received 2013-07-15
Accepted 2013-08-06
Published 2013-12-31


Main Article Content

Bharat Kumar Bugata
Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Satya Venkata Gopala Krishna Kaladhar Dowluru
Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Vasudeva Rao Avupati
Pharmaceutical Chemistry Division, Andhra University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530003, Andhra Pradesh, India
Venkateswara Rao Gavalapu
Pharmaceutical Chemistry Division, Andhra University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530003, Andhra Pradesh, India
Divakara Laxman Somayajulu Nori
Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Sreenu Barla
Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India

Abstract

A series of some new diarylsulfonylurea-chalcone hybrids (4a-4y) have been synthesized via Claisen-Schmidt condensation reaction by treating 1-(3-acetylphenyl)-3-tosylurea with various aromatic/heteroaromatic aldehydes in the presence of alkali and characterized by FT-IR, 1H NMR, 13C NMR and LC mass spectral analysis. All the synthesized compounds were evaluated for their in vitro 5-Lipoxygenase inhibitory activity using potato 5-lipoxygenase enzyme. Among the tested compounds 4r and 4o exhibited significant inhibitory activity at IC50 values 7.88±0.14 and 11.77±0.21 µg/mL, respectively. This level of activity was found comparable to that of the reference drug Abietic acid (LI01020) with IC50 value 4.34±0.37 µg/mL and it could be a remarkable starting point to develop new lead molecules.

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Bugata, B. K.; Dowluru, S. V. G. K. K.; Avupati, V. R.; Gavalapu, V. R.; Nori, D. L. S.; Barla, S. Synthesis, Characterization and in Vitro Biological Evaluation of Some New Diarylsulfonylurea-Chalcone Hybrids As Potential 5-Lipoxygenase Inhibitors. Eur. J. Chem. 2013, 4, 396-401.

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References

[1]. Kenyon, V.; Chorny, I.; Carvajal, W. J.; Holman, T. R.; Jacobson, M.P. J. Med. Chem. 2006, 49, 1356-1363.
http://dx.doi.org/10.1021/jm050639j
PMid:16480270

[2]. Werz, O. Curr. Drug Targets Inflamm. Allergy. 2002, 1, 23-44.
http://dx.doi.org/10.2174/1568010023344959
PMid:14561204

[3]. Babu, M. A.; Shakya, N.; Prathipati, P.; Kaskhedikara, S. G.; Saxena, A. K. Bioorgan. Med. Chem. 2002, 10, 4035-4041.
http://dx.doi.org/10.1016/S0968-0896(02)00313-9

[4]. Zhang, H. B.; Zhang, Y. A.; Wu, G. Z.; Zhou, J. P.; Huang, W. L.; Hu, X. W. Bioorg. Med. Chem. Lett. 2009, 19, 1740-1744.
http://dx.doi.org/10.1016/j.bmcl.2009.01.082
PMid:19216076

[5]. Frezza, M.; Soulere, L.; Reverchon, S.; Guiliani, N.; Jerez, C.; Queneau, Y.; Doutheau, A. Bioorg. Med. Chem. Lett. 2008, 16, 3550-3556.
http://dx.doi.org/10.1016/j.bmc.2008.02.023
PMid:18294853

[6]. Winters, M. P.; Crysler, C.; Subasinghe, N.; Ryan, D.; Leong, L.; Zhao, S.; Donatelli, R.; Yurkow, E.; Mazzulla, M.; Boczon, L.; Manthey, C. L.; Molloy, C.; Raymond, H.; Murray, L.; McAlonan, L.; Tomczuka, B. Bioorg. Med. Chem. Lett. 2008, 18, 1926-1930.
http://dx.doi.org/10.1016/j.bmcl.2008.01.127
PMid:18308567

[7]. Leon, C.; Rodrigues, J.; Dominguez, N. G. D.; Charris, J.; Gut, J.; Rosenthal, P. J.; Dominguez, J. N. Eur. J. Med. Chem. 2007, 42, 735-742.
http://dx.doi.org/10.1016/j.ejmech.2007.01.001
PMid:17321641

[8]. Ameya, A.; Chavan, C.; Nandini, R. P. J. Chin. Chem. Soc. 2007, 54, 771-777.

[9]. Hanson, J.; Dogne, J. M.; Ghiotto, J.; Moray, A. L.; Kinsella, B. T.; Pirotte, B. J. Med. Chem. 2007, 50, 3928-3936.
http://dx.doi.org/10.1021/jm070427h
PMid:17630727

[10]. Lehr, P.; Billich, A.; Wolff, B.; Nussbaumer, P. Bioorg. Med. Chem. Lett. 2005, 15, 1235-1238.
http://dx.doi.org/10.1016/j.bmcl.2004.11.069
PMid:15686949

[11]. Salamon, E.; Mannhold, R.; Weber, H.; Lemoine, H.; Frank, W. J. Med. Chem. 2002, 45, 1086-1089.
http://dx.doi.org/10.1021/jm010999g

[12]. Heitsch, H.; Becker, A. H. R.; Kleemann, W. H.; Wagner, A. Bioorgan. Med. Chem. 1997, 5, 673-678.
http://dx.doi.org/10.1016/S0968-0896(97)00012-6

[13]. Toth, E. J.; Grindey, B. G.; Ehlhardt, J. W.; Ray, E. J.; Boder, G. B.; Bewley, R. J.; Klingerman, K. K.; Gates, B. S.; Rinzel, M. S.; Schultz, R. M.; Weir, L. C.; Worzalla, F. J. J. Med. Chem. 1997, 40, 1018-1025.
http://dx.doi.org/10.1021/jm960673l
PMid:9083492

[14]. Picard, A. J.; Obrien, M. P.; Sliskovic, R. D.; Anderson, K. M.; Bousley, F. R.; Hamelehle, L. K.; Krause, R. B.; Stanfield, L. R. J. Med. Chem. 1996, 39, 1243-1252.
http://dx.doi.org/10.1021/jm9509455
PMid:8632431

[15]. Khelili, S.; Leclerc, G.; Faury, G.; Verdetti, J. Bioorgan. Med. Chem. 1995, 5, 495-503.
http://dx.doi.org/10.1016/0968-0896(95)00040-N

[16]. Lee, C. J. M.; Elberling, A. J.; Nagasawa, T. H. J. Med. Chem. 1992, 35, 3641-3647.
http://dx.doi.org/10.1021/jm00098a007

[17]. Mohamadi, F.; Spees, M. M.; Grindey, B. G. J. Med. Chem. 1992, 35, 3012-3016.
http://dx.doi.org/10.1021/jm00094a013

[18]. Love, B.; Snader, M. K. J. Med. Chem. 1968, 2, 1251-1270.

[19]. Uehling, E. D.; Donaldson, H. K.; Deaton, N. D.; Hyman, E. C.; Sugg, E. E.; Barrett, G. D.; Hughes, G. R.; Reitter, B.; Adkison, K. K.; Lancaster, E. M.; Lee, F.; Hart, R.; Paulik, A. M.; Sherman, W. B.; True, T.; Cowan, C. J. Med. Chem. 2002, 45, 567-583.
http://dx.doi.org/10.1021/jm0101500

[20]. Choi, J. K.; Noh, M. K.; Choi, D. J.; Park, S. J.; Won, S. H.; Kim, R. J.; Kim, S. J.; Yoon, M. Y. B Korean Chem. Soc. 2006, 10, 1697-1700.

[21]. Shuichi, F.; Masanori, I.; Atsutaka, Y.; Makoto, M.; Morihiro, M.; Iichiro, S. J. Biol. Chem. 2005, 24, 23653-23659.

[22]. Dinkova, K. A. T.; Massiah, M. A.; Bozak, R. E.; Hicks, R. J.; Talalay P. P. Natl. Acad. Sci. USA 2001, 98, 3404-3409.
http://dx.doi.org/10.1073/pnas.051632198
PMid:11248091 PMCid:PMC30666

[23]. Nakagawa, G.; Lee, K. Tetrahedron Lett. 2006, 47, 8263-8265.
http://dx.doi.org/10.1016/j.tetlet.2006.09.110

[24]. Narender, T.; Shweta; Gupta S. Bioorg. Med. Chem. Lett. 2004, 14(15), 3913-3916.
http://dx.doi.org/10.1016/j.bmcl.2004.05.071
PMid:15225696

[25]. Nielsen, S. F.; Chen, M.; Theander, T. G.; Kharazmi, A.; Christensen, S. B. Bioorg. Med. Chem. Lett. 1995, 5, 449-452.
http://dx.doi.org/10.1016/0960-894X(95)00053-V

[26]. Wu, J. H.; Wang, X. H.; Lee, K. H. Bioorgan. Med. Chem. 2003, 13, 1813-1815.
http://dx.doi.org/10.1016/S0960-894X(03)00197-5

[27]. Wu, X.; Wilairat, P.; Go, M. Bioorg. Med. Chem. Lett. 2002, 12, 2299-2302.
http://dx.doi.org/10.1016/S0960-894X(02)00430-4

[28]. Phrutivorapongkul, A.; Kirtikaro, K. Chem. Pharm. Bull. 2003, 51(6), 746-748.

[29]. Kumar, S. K.; Hager, E.; Pettit, C.; Gurulingappa, H.; Davidson, N. E.; Khan, S. R. J. Med. Chem. 2003, 46, 2813-2815.
http://dx.doi.org/10.1021/jm030213+
PMid:12825923

[30]. Narender, T.; Khaliq, T.; Shweta, N.; Gupta, S. Bioorgan. Med. Chem. 2005, 13, 6543-6550.
http://dx.doi.org/10.1016/j.bmc.2005.07.005
PMid:16185885

[31]. Nakaido, T.; Ohmoto, T. Chem. Pharm. Bull. 1984, 32(12), 4929-4934.
http://dx.doi.org/10.1248/cpb.32.4929

[32]. Kostanekki, S. T.; Szabranki, W. Ber. Dtsch. Chem. Ges. 1904, 37, 2634-2635.
http://dx.doi.org/10.1002/cber.19040370321

[33]. Jun, N.; Hong, G.; Jun, K. Bioorgan. Med. Chem. 2007, 15(6), 2396-2402.
http://dx.doi.org/10.1016/j.bmc.2007.01.017
PMid:17267225

[34]. Zhao, L. M.; Jin, H. S.; Sun, L. P.; Piao, H. R.; Quan, Z. S. Bioorg. Med. Chem. Lett. 2005, 15(22), 5027-5029.
http://dx.doi.org/10.1016/j.bmcl.2005.08.039
PMid:16169724

[35]. Assia, S.; Kaddour, L.; Mahieddine, M.; Nouara, Z.; Paul, M. Eur. J. Chem. 2011, 2(3), 311-313.
http://dx.doi.org/10.5155/eurjchem.2.3.311-313.414

[36]. Mohammed, R. A.; Mohammed, H. R. K.; Vedula, G. S.; Nasreen, B.; Syed, A.; Yejella, R. P. Eur. J. Chem. 2012, 3(2), 186-190.
http://dx.doi.org/10.5155/eurjchem.3.2.186-190.554

[37]. Mohammed, S. B.; Aly, A. A.; Ashraf, F. W.; Marwa, M. R. Eur. J. Chem. 2013, 4(2), 92-97.
http://dx.doi.org/10.5155/eurjchem.4.2.92-97.615

[38]. Avupati, V. R.; Yejella, R. P.; Guntuku, G.; Gunta, P. Bioorg. Med. Chem. Lett. 2012, 22, 1031-1035.
http://dx.doi.org/10.1016/j.bmcl.2011.11.125
PMid:22200598

[39]. Claisen, L.; Claparede A. Ber. 1881, 14, 2463-2479.

[40]. Sircar, J. C.; Shwender, C. J.; Johnson, E. A. Prostaglandins 1983, 25, 393-396.
http://dx.doi.org/10.1016/0090-6980(83)90042-4

[41]. Reddenna, P.; Whelan, J.; Maddipati, R. K. R. Methods Enzymol. 1990, 187, 268-277.
http://dx.doi.org/10.1016/0076-6879(90)87031-W

[42]. Ulusu, N. N.; Ercil, D.; Sakar, M. K.; Tezcan, E. E. Phytother. Res. 2002, 16, 88-90.
http://dx.doi.org/10.1002/ptr.983
PMid:11807975

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Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
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