Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Antimicrobial Evaluation of (E)-N'-[(1-(2-methoxy-6-pentadecylbenzyl)-1H-1,2,3-triazol-4-yl]methylene)benzohydrazide Derivatives
Corresponding Author(s) : N. Rambabu
Asian Journal of Chemistry,
Vol. 28 No. 1 (2016): Vol 28 Issue 1
Abstract
Anacardic acid (pentadecyl salicylic acid) is a phenolic constituent present in cashew nut shell liquid (Anacardium occidentale L.) and exhibits antimicrobial properties. The present paper describes the synthesis, characterization and antimicrobial evaluation of hydrazone derivatives of anacardic acid (9a-l) linked with 1,2,3-triazole ring. All the newly synthesized compounds were determined by 1H NMR, mass and IR spectroscopy. Compounds 9d, 9e, 9h, 9i and 9j exhibited strong antifungal activity against the tested fungal strains viz., A. niger and C. albicans.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- R. Kharb, M.S. Yar and P.C. Sharma, Mini Rev. Med. Chem., 11, 84 (2011); doi:10.2174/138955711793564051.
- K. Masuda, T. Toga and N. Hayashi, J. Label. Comp. Radiopharm., 11, 301 (1975); doi:10.1002/jlcr.2590110219.
- D.J. Prasad, M. Ashok, P. Karegoudar, B. Poojary, B.S. Holla and N.S. Kumari, Eur. J. Med. Chem., 44, 551 (2009); doi:10.1016/j.ejmech.2008.03.025.
- G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet and D. Kaya, Eur. J. Med. Chem., 40, 607 (2005); doi:10.1016/j.ejmech.2005.01.007.
- M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); doi:10.1016/j.ejmech.2004.02.008.
- B.S. Holla, K.N. Poojary, B.S. Rao and M.K. Shivananda, Eur. J. Med. Chem., 37, 511 (2002); doi:10.1016/S0223-5234(02)01358-2.
- B.S. Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.
- K. Walczak, A. Gondela and J. Suwiński, Eur. J. Med. Chem., 39, 849 (2004); doi:10.1016/j.ejmech.2004.06.014.
- A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.
- S. Rollas, N. Gulerman and H. Erdeniz, Farmaco, 57, 171 (2002); doi:10.1016/S0014-827X(01)01192-2.
- S.G. Kucukguzel, S. Rollas, I. Kucukguzel and M. Kiraz, Eur. J. Med. Chem., 34, 1093 (1999); doi:10.1016/S0223-5234(99)00129-4.
- S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
- I. Kubo, H. Muroi, M. Himejima, Y. Yamagiwa, H. Mera, K. Tokushima, S. Ohta and T. Kamikawa, J. Agric. Food Chem., 41, 1016 (1993); doi:10.1021/jf00030a036.
- J.L. Gellerman, N.J. Walsh, N.K. Werner and H. Schlenk, Can. J. Microbiol., 15, 1219 (1969); doi:10.1139/m69-220.
- M. Toyomizu, K. Okamoto, T. Ishibashi, Z. Chen and T. Nakatsu, Life Sci., 66, 229 (1999); doi:10.1016/S0024-3205(99)00585-8.
- B. Prithiviraj, U.P. Singh, M. Manickam and A.B. Ray, Can. J. Bot., 75, 207 (1997); doi:10.1139/b97-021.
- H. Muroi and I. Kubo, J. Appl. Microbiol., 80, 387 (1996); doi:10.1111/j.1365-2672.1996.tb03233.x.
- J. Kubo, J.R. Lee and I. Kubo, J. Agric. Food Chem., 47, 533 (1999); doi:10.1021/jf9808980.
- B.E. Rivero-Cruz, N. Esturau, S. Sánchez-Nieto, I. Romero, I. Castillo-Juárez and J.F. Rivero-Cruz, Nat. Prod. Res., 25, 1282 (2011); doi:10.1080/14786419.2010.534996.
- S.V. Shobha, C.S. Ramadoss and B. Ravindranath, J. Nat. Prod., 57, 1755 (1994); doi:10.1021/np50114a025.
- T.J. Ha and I. Kubo, J. Agric. Food Chem., 53, 4350 (2005); doi:10.1021/jf048184e.
- V. Chandregowda, A. Kush and G.C. Reddy, Eur. J. Med. Chem., 44, 2711 (2009); doi:10.1016/j.ejmech.2009.01.033.
- P. Phanikumar, S.C. Stotz, R. Paramashivappa, M. Beedle, G.W. Zamponi and A. Srinivasa Rao, Mol. Pharmacol., 61, 649 (2002); doi:10.1124/mol.61.3.649.
- R. Paramashivappa, P. Phanikumar, P.V. Subba Rao and A. Srinivasa Rao, J. Agric. Food Chem., 50, 7709 (2002); doi:10.1021/jf0258050.
- B. Narayana Swamy, T.K. Suma, G. Venkateswara Rao and G. Chandrasekara Reddy, Eur. J. Med. Chem., 42, 420 (2007); doi:10.1016/j.ejmech.2006.09.009.
- A.H. Kishore, B.M. Vedamurthy, K. Mantelingu, S. Agrawal, B.A.A. Reddy, S. Roy, K.S. Rangappa and T.K. Kundu, J. Med. Chem., 51, 792 (2008); doi:10.1021/jm700954w.
- B. Sung, M.K. Pandey, K.S. Ahn, T. Yi, M.M. Chaturvedi, M. Liu and B.B. Aggarwal, Blood, 111, 4880 (2008); doi:10.1182/blood-2007-10-117994.
- L. Cui, J. Miao, T. Furuya, Q. Fan, X. Li, P.K. Rathod, X.Z. Su and L. Cui, Eukaryot. Cell, 7, 1200 (2008); doi:10.1128/EC.00063-08.
- G.H. Cassell and J. Mekalanos, JAMA, 285, 601 (2001); doi:10.1001/jama.285.5.601.
- S.K. Mamidyala, S. Ramu, J.X. Huang, A.A. Robertson and M.A. Copper, Bioorg. Med. Chem. Lett., 23, 1667 (2013); doi:10.1016/j.bmcl.2013.01.074.
- R. Wisastra, M. Ghizzoni, A. Boltjes, H.J. Haisma and F.J. Dekker, Bioorg. Med. Chem., 20, 5027 (2012); doi:10.1016/j.bmc.2012.06.019.
- R. Wisastra, P.A.M. Kok, N. Eleftheriadis, M.P. Baumgartner, C.J. Camacho, H.J. Haisma and F.J. Dekker, Bioorg. Med. Chem., 21, 7763 (2013); doi:10.1016/j.bmc.2013.10.015.
- M.J. Rybak and R.L. Akins, Drugs, 61, 1 (2001); doi:10.2165/00003495-200161010-00001.
- Y. Cetinkaya, P. Falk and C.G. Mayhall, Clin. Microbiol.Rev., 13, 686 (2000); doi:10.1128/CMR.13.4.686-707.2000.
- D. Srinivasan, S. Nathan, T. Suresh and P. Lakshmana Perumalsamy, J. Ethnopharmacol., 74, 217 (2001); doi:10.1016/S0378-8741(00)00345-7.
- N.S. Reddy, V.R. Kumar, V. Himabindu, B. Ram and A.S. Rao, Lett. Drug Des.Discov., 8, 626 (2011); doi:10.2174/157018011796235167.
- N. Subhakara Reddy, V. Ravi Kumar, V. Himabindu, B. Ram and A. Srinivas Rao, Lett. Drug Des.Discov., 8, 972 (2011); doi:10.2174/157018011797655278.
- N.S. Reddy, A.S. Rao, M.A. Chari, V.R. Kumar, V. Jyothi and V. Himabindu, Int. J. Org. Chem., 1, 167 (2011); doi:10.4236/ijoc.2011.14025.
- N.S. Reddy, A.S. Rao and M.A. Chari, Lett. Org. Chem., 9, 287 (2012); doi:10.2174/157017812800233660.
- N.S. Reddy, A.S. Rao, M.A. Chari, R. Kumar, V. Jyothy and V. Himabindu, J. Chem. Sci., 124, 723 (2012); doi:10.1007/s12039-012-0253-1.
- J.C.S. da Costa, K.C. Pais, E.L. Fernandes, P.S.M. de Oliveira, J.S. Mendonça, M.V.N. de Souza, M.A. Peralta and T.R.A. Vasconcelos, ARKIVOC, 128 (2006); doi:10.3998/ark.5550190.0007.115.
- V.S.C. de Andrade and M.C.S. de Mattos, J. Braz. Chem. Soc., 25, 975 (2014); doi:10.5935/0103-5053.20140055.
References
R. Kharb, M.S. Yar and P.C. Sharma, Mini Rev. Med. Chem., 11, 84 (2011); doi:10.2174/138955711793564051.
K. Masuda, T. Toga and N. Hayashi, J. Label. Comp. Radiopharm., 11, 301 (1975); doi:10.1002/jlcr.2590110219.
D.J. Prasad, M. Ashok, P. Karegoudar, B. Poojary, B.S. Holla and N.S. Kumari, Eur. J. Med. Chem., 44, 551 (2009); doi:10.1016/j.ejmech.2008.03.025.
G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet and D. Kaya, Eur. J. Med. Chem., 40, 607 (2005); doi:10.1016/j.ejmech.2005.01.007.
M. Amir and K. Shikha, Eur. J. Med. Chem., 39, 535 (2004); doi:10.1016/j.ejmech.2004.02.008.
B.S. Holla, K.N. Poojary, B.S. Rao and M.K. Shivananda, Eur. J. Med. Chem., 37, 511 (2002); doi:10.1016/S0223-5234(02)01358-2.
B.S. Holla, B. Veerendra, M.K. Shivananda and B. Poojary, Eur. J. Med. Chem., 38, 759 (2003); doi:10.1016/S0223-5234(03)00128-4.
K. Walczak, A. Gondela and J. Suwiński, Eur. J. Med. Chem., 39, 849 (2004); doi:10.1016/j.ejmech.2004.06.014.
A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem. Lett., 14, 6057 (2004); doi:10.1016/j.bmcl.2004.09.072.
S. Rollas, N. Gulerman and H. Erdeniz, Farmaco, 57, 171 (2002); doi:10.1016/S0014-827X(01)01192-2.
S.G. Kucukguzel, S. Rollas, I. Kucukguzel and M. Kiraz, Eur. J. Med. Chem., 34, 1093 (1999); doi:10.1016/S0223-5234(99)00129-4.
S.G. Kucukguzel, E.E. Oruc, S. Rollas, F. Sahin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
I. Kubo, H. Muroi, M. Himejima, Y. Yamagiwa, H. Mera, K. Tokushima, S. Ohta and T. Kamikawa, J. Agric. Food Chem., 41, 1016 (1993); doi:10.1021/jf00030a036.
J.L. Gellerman, N.J. Walsh, N.K. Werner and H. Schlenk, Can. J. Microbiol., 15, 1219 (1969); doi:10.1139/m69-220.
M. Toyomizu, K. Okamoto, T. Ishibashi, Z. Chen and T. Nakatsu, Life Sci., 66, 229 (1999); doi:10.1016/S0024-3205(99)00585-8.
B. Prithiviraj, U.P. Singh, M. Manickam and A.B. Ray, Can. J. Bot., 75, 207 (1997); doi:10.1139/b97-021.
H. Muroi and I. Kubo, J. Appl. Microbiol., 80, 387 (1996); doi:10.1111/j.1365-2672.1996.tb03233.x.
J. Kubo, J.R. Lee and I. Kubo, J. Agric. Food Chem., 47, 533 (1999); doi:10.1021/jf9808980.
B.E. Rivero-Cruz, N. Esturau, S. Sánchez-Nieto, I. Romero, I. Castillo-Juárez and J.F. Rivero-Cruz, Nat. Prod. Res., 25, 1282 (2011); doi:10.1080/14786419.2010.534996.
S.V. Shobha, C.S. Ramadoss and B. Ravindranath, J. Nat. Prod., 57, 1755 (1994); doi:10.1021/np50114a025.
T.J. Ha and I. Kubo, J. Agric. Food Chem., 53, 4350 (2005); doi:10.1021/jf048184e.
V. Chandregowda, A. Kush and G.C. Reddy, Eur. J. Med. Chem., 44, 2711 (2009); doi:10.1016/j.ejmech.2009.01.033.
P. Phanikumar, S.C. Stotz, R. Paramashivappa, M. Beedle, G.W. Zamponi and A. Srinivasa Rao, Mol. Pharmacol., 61, 649 (2002); doi:10.1124/mol.61.3.649.
R. Paramashivappa, P. Phanikumar, P.V. Subba Rao and A. Srinivasa Rao, J. Agric. Food Chem., 50, 7709 (2002); doi:10.1021/jf0258050.
B. Narayana Swamy, T.K. Suma, G. Venkateswara Rao and G. Chandrasekara Reddy, Eur. J. Med. Chem., 42, 420 (2007); doi:10.1016/j.ejmech.2006.09.009.
A.H. Kishore, B.M. Vedamurthy, K. Mantelingu, S. Agrawal, B.A.A. Reddy, S. Roy, K.S. Rangappa and T.K. Kundu, J. Med. Chem., 51, 792 (2008); doi:10.1021/jm700954w.
B. Sung, M.K. Pandey, K.S. Ahn, T. Yi, M.M. Chaturvedi, M. Liu and B.B. Aggarwal, Blood, 111, 4880 (2008); doi:10.1182/blood-2007-10-117994.
L. Cui, J. Miao, T. Furuya, Q. Fan, X. Li, P.K. Rathod, X.Z. Su and L. Cui, Eukaryot. Cell, 7, 1200 (2008); doi:10.1128/EC.00063-08.
G.H. Cassell and J. Mekalanos, JAMA, 285, 601 (2001); doi:10.1001/jama.285.5.601.
S.K. Mamidyala, S. Ramu, J.X. Huang, A.A. Robertson and M.A. Copper, Bioorg. Med. Chem. Lett., 23, 1667 (2013); doi:10.1016/j.bmcl.2013.01.074.
R. Wisastra, M. Ghizzoni, A. Boltjes, H.J. Haisma and F.J. Dekker, Bioorg. Med. Chem., 20, 5027 (2012); doi:10.1016/j.bmc.2012.06.019.
R. Wisastra, P.A.M. Kok, N. Eleftheriadis, M.P. Baumgartner, C.J. Camacho, H.J. Haisma and F.J. Dekker, Bioorg. Med. Chem., 21, 7763 (2013); doi:10.1016/j.bmc.2013.10.015.
M.J. Rybak and R.L. Akins, Drugs, 61, 1 (2001); doi:10.2165/00003495-200161010-00001.
Y. Cetinkaya, P. Falk and C.G. Mayhall, Clin. Microbiol.Rev., 13, 686 (2000); doi:10.1128/CMR.13.4.686-707.2000.
D. Srinivasan, S. Nathan, T. Suresh and P. Lakshmana Perumalsamy, J. Ethnopharmacol., 74, 217 (2001); doi:10.1016/S0378-8741(00)00345-7.
N.S. Reddy, V.R. Kumar, V. Himabindu, B. Ram and A.S. Rao, Lett. Drug Des.Discov., 8, 626 (2011); doi:10.2174/157018011796235167.
N. Subhakara Reddy, V. Ravi Kumar, V. Himabindu, B. Ram and A. Srinivas Rao, Lett. Drug Des.Discov., 8, 972 (2011); doi:10.2174/157018011797655278.
N.S. Reddy, A.S. Rao, M.A. Chari, V.R. Kumar, V. Jyothi and V. Himabindu, Int. J. Org. Chem., 1, 167 (2011); doi:10.4236/ijoc.2011.14025.
N.S. Reddy, A.S. Rao and M.A. Chari, Lett. Org. Chem., 9, 287 (2012); doi:10.2174/157017812800233660.
N.S. Reddy, A.S. Rao, M.A. Chari, R. Kumar, V. Jyothy and V. Himabindu, J. Chem. Sci., 124, 723 (2012); doi:10.1007/s12039-012-0253-1.
J.C.S. da Costa, K.C. Pais, E.L. Fernandes, P.S.M. de Oliveira, J.S. Mendonça, M.V.N. de Souza, M.A. Peralta and T.R.A. Vasconcelos, ARKIVOC, 128 (2006); doi:10.3998/ark.5550190.0007.115.
V.S.C. de Andrade and M.C.S. de Mattos, J. Braz. Chem. Soc., 25, 975 (2014); doi:10.5935/0103-5053.20140055.