European Journal of Chemistry

Synthesis, characterization and in vitro biological evaluation of some new 1,3,5-triazine-bis-azomethine hybrid molecules as potential antitubercular agents

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Published: Jun 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.2.374-379.1027
Keywords:
H37Rv, Hybrid molecules, Antitubercular activity, Mycobacterium tuberculosis, 1, 3, 5-Triazine-bis-azomethine, Minimum inhibitory concentration
Section
Research Article
Issue
Vol. 5 No. 2 (2014): June 2014
Dates
Received 2014-02-02
Accepted 2014-03-08
Published 2014-06-30


Main Article Content

Madhusudana Rao Gajula
Department of Chemistry, Sri Venkateswara University, Tirupati-517502, Andhra Pradesh, India
Yellala Venkata Rami Reddy
Department of Chemistry, Sri Venkateswara University, Tirupati-517502, Andhra Pradesh, India

Abstract

A series of 1,3,5-triazine-bis-azomethinehybrid molecules (4a-p and 5a-p) were synthesized and tested against Mycobacterium tuberculosis H37Rv strain. Preparation of the titled compounds was achieved by reaction of N-(4-aminobenzylidene)-4-methoxy-6-methyl-1,3,5-triazin-2-amine (3) with aromatic/heteroaromatic aldehydes (4a-p)and ketones (5a-p). Among the compounds tested, (4d) was identified as the most active in vitro with MIC value 3.125 µg/mL against Mycobacterium tuberculosis H37Rv.


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Gajula, M. R.; Reddy, Y. V. R. Synthesis, Characterization and in Vitro Biological Evaluation of Some New 1,3,5-Triazine-Bis-Azomethine Hybrid Molecules As Potential Antitubercular Agents. Eur. J. Chem. 2014, 5, 374-379.

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References

[1]. Ohsawa, A.; Arai, H.; Ohnishi, H.; Igeta, H. J. Chem. Soc. Chem. Commun. 1981, 1, 1173-1174.

[2]. Grzegorz, B. Tetrahedron 2006, 62, 9507-9522.
http://dx.doi.org/10.1016/j.tet.2006.07.039

[3]. Kim, K. H.; Dietrich, S. W.; Hansch, C.; Dolnick, B. J.; Bertino, J. R. J. Med. Chem. 1980, 23, 1248-1251.
http://dx.doi.org/10.1021/jm00185a022

[4]. Blaney, J. M.; Hansch, C.; Silipo, C.; Vittoria, A. Chem. Rev. 1984, 84, 333-407.
http://dx.doi.org/10.1021/cr00062a002

[5]. Foster, B. J.; Harding, B. J. Leyland-Jones, B.; Hoth, D. Cancer Treat. Rev. 1986, 38, 197-217.
http://dx.doi.org/10.1016/0305-7372(86)90006-X

[6]. Labrid, C.; Regnier, G. L.; Laubie, M. Eur. J. Respir. Dis. 1983, 64, 185-189.

[7]. Ono, M.; Kawahara, N.; Goto, D.; Wakabayashi, Y.; Ushiro, S.; Yoshida, S.; Izumi, H.; Kuwano, M.; Sato, Y. Cancer Res. 1996, 56(7), 1512-1516.

[8]. Baker, B. R.; Ashton, W. T. J. Med. Chem. 1973, 16, 209-214.
http://dx.doi.org/10.1021/jm00261a009

[9]. Sirawaraporn, W.; Sathitkul, T.; Sirawaraporn, R.; Yuthavong, Y.; Santi, D. V. Proc. Natl. Acad. Sci. 1997, 94, 1124-1129.
http://dx.doi.org/10.1073/pnas.94.4.1124

[10]. Patel, R. V.; Kumari, P.; Rajani, D. P.; Chikhalia, K. H. Eur. J. Med. Chem. 2011, 46, 4354-4365.
http://dx.doi.org/10.1016/j.ejmech.2011.07.006

[11]. Pastorin, G.; S. Federico, S.; S. Paoletta, S.; Corradino, M.; Cateni, F.; Cacciari, B.; Klotz, K.; Gao, Z.; Jacobson, K. A.; Spalluto, G.; Moro, S. Bioorg. Med. Chem. 2010, 18, 2524-2536.
http://dx.doi.org/10.1016/j.bmc.2010.02.039

[12]. Pastorin, G.; S. Federico, S.; S. Paoletta, S.; Corradino, M.; Cateni, F.; Cacciari, B.; Klotz, K.; Gao, Z.; Jacobson, K. A.; Spalluto, G.; Moro, S. Bioorg. Med. Chem. 2010, 18, 2524-2536.
http://dx.doi.org/10.1016/j.bmc.2010.02.039

[13]. Popowycz, F.; Schneider, C.; DeBonis, S.; Skoufias, D. A.; Kozielski, F.; Galmarini, C. M.; Joseph, B. Bioorg. Med. Chem. 2009, 17, 3471-3478.
http://dx.doi.org/10.1016/j.bmc.2009.03.007

[14]. Sunduru, N.; Agarwal, A.; Katiyar, S. B.; Nishi, N.; Goyal, N.; Guptab, S.; Chauhana, P. M. S. Bioorg. Med. Chem. 2006, 14, 7706-7715.
http://dx.doi.org/10.1016/j.bmc.2006.08.009

[15]. Vilaivan, T.; Saesaengseerung, N.; Jarprung, D.; Kamchonwongpaisan, S.; Sirawaraporn, W.; Yuthavong, Y. Bioorg. Med. Chem. 2003, 11, 217-224.
http://dx.doi.org/10.1016/S0968-0896(02)00344-9

[16]. Zhou, C.; Min, J.; Liu, Z.; Young, A.; Deshazer, H.; Gao, T.; Chang, Y. T.; Kallenbach, N. R. Bioorg. Med. Chem. Lett. 2008, 18, 1308-1311.
http://dx.doi.org/10.1016/j.bmcl.2008.01.031

[17]. Krecmerova, M.; Masojidkova, M.; Holy, A. Bioorg. Med. Chem. 2010, 18, 387-395.
http://dx.doi.org/10.1016/j.bmc.2009.10.044

[18]. Sunduru, N.; Gupta, L.; Chaturvedi, V.; Dwivedi, R.; Sinha, S.; Chauhan, P. M. S. Eur. J. Med. Chem. 2010, 45, 3335-3345.
http://dx.doi.org/10.1016/j.ejmech.2010.04.017

[19]. Garaj, V.; Puccetti, L.; Fasolis, G.; Winum, J.; Montero, J.; Scozzafava, A.; Vullo, D.; Innocentia, A.; Supurana, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 3102-3108.
http://dx.doi.org/10.1016/j.bmcl.2005.04.056

[20]. Sosic, I.; Mirkovi, B.; Turk, S.; Stefane, B.; Kos, J.; Gobec, S. Eur. J. Med. Chem. 2011, 46, 4648-4656.
http://dx.doi.org/10.1016/j.ejmech.2011.08.005

[21]. Xia, Y.; Mirzai, B.; Chackalamannil, S.; Czamiecki, M.; Wang, S.; Clemmons, A.; Ahn, H.; Boykow, G. C. Bioorg. Med. Chem. Lett. 1996, 6, 919-922.
http://dx.doi.org/10.1016/0960-894X(96)00145-X

[22]. Fitzgerald, L.; Miller, K.; Marshallyy, W. J. Bioorg. Med. Chem. 2003, 11, 4093-4102.
http://dx.doi.org/10.1016/S0968-0896(03)00398-5

[23]. Zuev, D.; Mattson, R. J.; Huang, H.; Mattson, G. K.; Zueva, L.; Nielsen, J. M.; Kozlowski, E. S.; Huang, X. S.; Wua, D.; Gao, Q.; Lodge, N. J.; Bronson, J. J.; Macor, J. E. Bioorg. Med. Chem. Lett. 2011, 21, 2484-2488.
http://dx.doi.org/10.1016/j.bmcl.2011.02.050

[24]. Gopalsamy, A.; Yang, H.; Ellingboe, J. W.; McKew, J. C.; Tam, S.; McCarthy, D.; Zhang, W.; Shen, M.; Clarke, J. D. Bioorg. Med. Chem. Lett. 2006, 16, 2978-2981.
http://dx.doi.org/10.1016/j.bmcl.2006.02.067

[25]. Andrews, K. M.; Beebe, D. A.; Benbow, J. W.; Boyer, D. A.; Doran, S. D.; Hui, Y.; Liu, S.; Kirk, M. R.; Neagu, C.; Parker, J. C.; Piotrowski, D. W.; Schneider, S. R.; Treadway, J. L.; VanVolkenberg, M. A.; Zembrowski, W. J. Bioorg. Med. Chem. Lett. 2011, 21, 1810-1814.
http://dx.doi.org/10.1016/j.bmcl.2011.01.055

[26]. McKay, G. A.; Reddy, R.; Arhin, F. S; Belley, A.; Lehoux, D.; Moeck, G.; Sarmiento, I.; Parr, T. R.; Gros, P.; Pelletier, J.; Fara, A. R. Bioorg. Med. Chem. Lett. 2006, 16, 1286-1290.
http://dx.doi.org/10.1016/j.bmcl.2005.11.076

[27]. Dehnhardt, C. M.; Venkatesan, A. M.; Chen, Z.; D. Santos, E.; A. Kaloustian, S.; Brooijmans, N.; Yu, K.; Hollander, I.; Feldberg, L.; Lucas, J.; Mallon, R. Bioorg. Med. Chem. Lett. 2011, 21, 4773-4778.
http://dx.doi.org/10.1016/j.bmcl.2011.06.063

[28]. Huang, W.; Zheng, W.; Urban, D. J.; Inglese, J.; Sidransky, E.; Austina, C. P.; Thomasa, C. J. Bioorg. Med. Chem. Lett. 2007, 17, 5783-5789.
http://dx.doi.org/10.1016/j.bmcl.2007.08.050

[29]. Park, H.; Hwang, K. Y.; Kim, Y. H.; Oh, K. H.; Lee, J. Y.; Kim, K. Bioorg. Med. Chem. Lett. 2008, 18, 3711-3715.
http://dx.doi.org/10.1016/j.bmcl.2008.05.056

[30]. Courme, C.; Gresh, N.; Vidal, M.; Lenoir, C.; Garbay, C.; Florent, J.; Bertounesque, E. Eur. J. Med. Chem. 2010, 45, 244-255.
http://dx.doi.org/10.1016/j.ejmech.2009.10.003

[31]. Guo, Z.; Wu, D.; Zhu, Y. F.; Tucci, F. C.; Pontillo, J.; Saunders, J.; Xie, Q.; Struthers, R. S.; Chena, C. Bioorg. Med. Chem. Lett. 2005, 15, 693-702.
http://dx.doi.org/10.1016/j.bmcl.2004.11.026

[32]. Mattson, R. J.; Denhart, D. J.; Catt, J. D.; Dee, M. F.; Deskus, J. A.; Ditta, J. L.; Epperson, J.; King, H. D.; Gao, A.; Poss, M. A.; Purandare, A.; Tortolani, D.; Zhao, Y.; Yang, H.; Yeola, S.; Palmer, J.; Torrente, J.; Stark, A.; Johnson, G. Bioorg. Med. Chem. Lett. 2004, 14, 4245-4248.
http://dx.doi.org/10.1016/j.bmcl.2004.06.008

[33]. Pitts, W. J.; Guo, J.; Dhar, T. G. M.; Shen, Z.; Gu, H. H.; Watterson, S. H.; Bednarz, M. S.; Chen, B.; Barrish, J. C.; Bassolino, D.; Cheney, D.; Fleener, C. A.; Rouleau, K. A.; Hollenbaugh, D. L.; Iwanowicz, E. J. Bioorg. Med. Chem. Lett. 2002, 12, 2137-2142.
http://dx.doi.org/10.1016/S0960-894X(02)00351-7

[34]. Richard, D. J.; Verheijen, J. C.; Yu, K.; Zask, A. Bioorg. Med. Chem. Lett. 2010, 20, 2654-2657.
http://dx.doi.org/10.1016/j.bmcl.2010.02.029

[35]. Bregman, H.; Nguyen, H. N.; Feric, E.; Ligutti, J.; Liu, D.; McDermott, J. S.; Wilenkin, B.; Zou, A.; Huang, L.; Li, X.; McDonough, S. I.; DiMauro, E. F. Bioorg. Med. Chem. Lett. 2012, 22, 2033-2042.
http://dx.doi.org/10.1016/j.bmcl.2012.01.023

[36]. Maa, X.; Poon, T. Y.; Hon Wong, P. T.; Chui, W. K. Bioorg. Med. Chem. Lett. 2009, 19, 5644-5647.
http://dx.doi.org/10.1016/j.bmcl.2009.08.052

[37]. Raboisson, P.; Schultz, D.; Muller, C.; Reimund, J.; Pinna, G.; Mathieu, R.; Bernard, P.; Do, Q.; DesJarlais, R. L.; Justiano, H.; Lugnier, C.; Bourguignon, J. Eur. J. Med. Chem. 2008, 43, 816-829.
http://dx.doi.org/10.1016/j.ejmech.2007.05.016

[38]. Nie, Z.; Perretta, C.; Erickson, P.; Margosiak, S.; Lu, J.; Averill, A.; Almassy, R.; Chua, S. Bioorg. Med. Chem. Lett. 2008, 18, 619-623.
http://dx.doi.org/10.1016/j.bmcl.2007.11.074

[39]. Ho, K. K.; Beasley, J. R.; Belanger, L.; Black, D.; Chan, J.; Dunn, D.; Hu, B.; Klon, A.; Kultgen, S. G.; Ohlmeyer, M.; Parlato, S. M.; Ray, P. C.; Pham, Q.; Rong, Y.; Roughton, A. L.; Walker, T. L.; Wright, J.; Xu, K.; Xu, Y.; Zhang, L.; Webba, M. Bioorg. Med. Chem. Lett. 2009, 19, 6031-6035.

[40]. Xu, W.; Chen, G.; Liew, O. W.; Zuo, Z.; Jiang, H.; Zhu, W. Bioorg. Med. Chem. Lett. 2009, 19, 3188-3192.
http://dx.doi.org/10.1016/j.bmcl.2009.04.113

[41]. Mylari, B. L.; Withbroe, G. J.; Beebe, D. A.; Brackett, N. S.; Conn, E. L.; Coutcher, J. B.; Oates P. J.; Zembrowski, W. J. Bioorg. Med. Chem. 2003, 11, 4179-4188.
http://dx.doi.org/10.1016/S0968-0896(03)00490-5

[42]. Jin, H.; Cianchetta, G.; Devasagayaraj, A.; Gua, K.; Marinelli, B.; Samala, L.; Scott, S.; Stouch, T.; Tunoori, A.; Wang, Y.; Zang, Y.; Zhang, C.; Kimball, S. D.; Main, A. J.; Ding, Z.; Sun, W.; Yang, Q.; Yu, X.; Powell, D. R.; Wilson, A.; Liu, Q.; Shi, Z. Bioorg. Med. Chem. Lett. 2009, 19, 5229-5232.
http://dx.doi.org/10.1016/j.bmcl.2009.07.005

[43]. Porter, J. R.; Archibald, S. C.; Brown, J. A.; Childs, K.; Critchley, D.; Head, J. C.; Hutchinson, B.; Parton, T. A. H.; Robinson, M. K.; Shock, A.; Warrellow, G. J.; Zomaya, A. Bioorg. Med. Chem. Lett. 2002, 12, 1591-1594.
http://dx.doi.org/10.1016/S0960-894X(02)00237-8

[44]. Jarrahpour, A.; Khalili, D.; De Clercq, E.; Salmi, C.; Brunel, J. M. Molecules 2007, 12, 1720-1730.
http://dx.doi.org/10.3390/12081720

[45]. Perumal, P.; Bilal, A. R.; Dontireddy, R. S. R.; Natesh, R. K. Eur. J. Med. Chem. 2009, 44, 2328-2340.
http://dx.doi.org/10.1016/j.ejmech.2008.04.010

[46]. Kui, C.; Qing, Z.; Yong, Q.; Lei, S.; Jing, Z.; Hai, Z. Bioorg. Med. Chem. 2009, 17, 7861-7871.
http://dx.doi.org/10.1016/j.bmc.2009.10.037

[47]. Panchal, P. K.; Pansuriya, P. B.; Patel, M. N. J. Enzyme Inhib. Med. Chem. 2006, 21, 453-458.

[48]. Jarrahpour, A.; Khalili, D.; De, C. E.; Salmi, C.; Brunel, J. M. Molecules 2007, 12, 1720-1730.
http://dx.doi.org/10.3390/12081720

[49]. Koneni, V. S.; Jammikuntla, N. R.; Gitika, B.; Saxena, J. K. Eur. J. Med. Chem. 2008, 43, 2592-2596.
http://dx.doi.org/10.1016/j.ejmech.2007.10.029

[50]. Vanco, J.; Svajlenova, O.; Racanska, E.; Muselik, J.; Valentova, J. J. Trace Elem. Med. Biol. 2004, 18, 155-161.

[51]. Ambike, V.; Adsule, S.; Ahmed, F.; Wang, Z.; Afrasiabi, Z.; Sinn, E.; Sarkar, F.; Padhye, S. J. Inorg. Biochem. 2007, 101, 1517-1524.
http://dx.doi.org/10.1016/j.jinorgbio.2007.06.028

[52]. Sinha, D.; Tiwari, A. K.; Singh, S.; Shukla, G.; Mishra, P.; Chandra, H.; Mishra, A. K. Eur. J. Med. Chem. 2008, 43, 160-165.
http://dx.doi.org/10.1016/j.ejmech.2007.03.022

[53]. Gihane, N.; Eddy, P.; Claudiu, T. S.; Jean-Yves, W.; Mihail, B. Bioorg. Med. Chem. Lett. 2009, 19, 6014-6017.
http://dx.doi.org/10.1016/j.bmcl.2009.09.047

[54]. You, Z.; Shi, D.; Xu, C.; Zhang, Q.; Zhu, H. Eur. J. Med. Chem. 2008, 43, 862-871.
http://dx.doi.org/10.1016/j.ejmech.2007.06.015

[55]. Amin, R.; Krammer, B.; Abdel-Kader, N.; Verwanger, T.; El-Ansary, A. Eur. J. Med. Chem. 2010, 45, 372-378.
http://dx.doi.org/10.1016/j.ejmech.2009.10.001

[56]. Pradeepkumar, M. R.; Malleshappa, N. N.; Sheetal, S.; Satyanarayana, D.; Veeresh, S. M. Eur. J. Med. Chem. 2010, 45, 85-89.
http://dx.doi.org/10.1016/j.ejmech.2009.09.028

[57]. Zahid, H. C.; Mahmood, U.; Khalid, M. K.; Claudiu, T. S. J. Enzyme Inhib. Med. Chem. 2005, 20, 183-188.

[58]. Bharti, S. K.; Nath, G.; Tilak, R.; Singh, S. K. Eur. J. Med. Chem. 2010, 45, 651-660.
http://dx.doi.org/10.1016/j.ejmech.2009.11.008

[59]. Ye, X.; Chen, Z.; Zhang, A.; Zhang, L. Molecules. 2007, 12, 1202-1209.
http://dx.doi.org/10.3390/12061202

[60]. Gacche, R. N.; Gond, D. S.; Dhole, N. A.; Dawane, B. S. J. Enzyme Inhib. Med. Chem. 2006, 21, 157-161.

[61]. Toyato, E.; Sekizaki, H.; Itoh, K.; Tanizawa, K. Chem. Pharm. Bull. 2003, 51, 625-629.
http://dx.doi.org/10.1248/cpb.51.625

[62]. Cardile, V.; Panico, A. M.; Geronikaki, A.; Gentile, B.; Ronsisvalle, G. Farmaco 2002, 57, 1009-1013.
http://dx.doi.org/10.1016/S0014-827X(02)01290-9

[63]. Doddareddy, M. R.; Cho, Y. S.; Koh, H. Y.; Pae, A. N. Bioorg. Med. Chem. 2004, 12, 3977-3985.
http://dx.doi.org/10.1016/j.bmc.2004.06.007

[64]. Jayashree, B. S.; Anuradha, D.; Venugopala, K. N. Asian J. Chem. 2005, 17, 2093-2097.

[65]. Bhandari, S. V.; Bothara, K. G.; Raut, M. K.; Patil, A. A.; Sarkate, A. P.; Mokale, V. J. Bioorg. Med. Chem. 2008, 16, 1822-1831.
http://dx.doi.org/10.1016/j.bmc.2007.11.014

[66]. Venugopala, K. N.; Jayashree, B. S. Asian J. Chem. 2004, 16, 407-411.

[67]. Sondhi, S. M.; Singh, N.; Kumar, A.; Meijer, O. L. L. Bioorg. Med. Chem. 2006, 14, 3758-3765.
http://dx.doi.org/10.1016/j.bmc.2006.01.054

[68]. Maria, C. S. L.; Marcus, V. N.; Alessandra, C. P.; Marcelle, L. F.; Goncalves, T, M.; Nogneira, M. A. P. Arkivoc 2007, 15, 181-191.

[69]. Bugata, B.; Krishna KaladharDowluru, S.; Avupati, V.; Gavalapu, V.; SomayajuluNori, D.; Barla, S. Eur. J. Chem. 2013, 4, 396-401.
http://dx.doi.org/10.5155/eurjchem.4.4.396-401.878

[70]. Zhang, H.; Ting, M.; Zhe, C.; Ziqi, Y.; Guolin, Z.; Yijia, L.; Yongping, Y. J. Comb. Chem. 2009, 11, 267–273.
http://dx.doi.org/10.1021/cc800157k

[71]. Musa, O.; Emre, M.; Bahittin, K. Eur. J. Chem. 2012, 3, 442-446.
http://dx.doi.org/10.5155/eurjchem.3.4.442-446.691

[72]. Vasudeva, R. A.; Rajendra, P. Y.; Venkateswara, R. P.; Kishore, N. K.; Venkata, M. R. P.; Prasad, C.; Venkateswara, R. G.; Bhavani, B. Bioorg. Med. Chem. 2013, 23, 5968-5970.
http://dx.doi.org/10.1016/j.bmcl.2013.08.063

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