Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Antimicrobial Activity of Dithiocarbamates of ω-Substituted (2-naphthyloxy)alkanes
Corresponding Author(s) : Sadaf Zaidi
Asian Journal of Chemistry,
Vol. 31 No. 10 (2019): Vol 31 Issue 10
Abstract
A series of dithiocarbamates of ω-substituted (2-naphthyloxy) alkanes was developed through condensation of 2-(2-chloro-alkoxy)-naphthalene to various kinds of aliphatic, aromatic, alicyclic, heterocyclic primary and secondary amines employing benzyl trimethyl ammonium hydroxide in catalytic quantity (Triton-B/CS2 system) afforded desired products in high yields (82-98 %). The complete series of synthesized compounds (4-48) were evaluated for antimicrobial activity through microdilution method using various bacterial and fungal strains. The antifungal and antibacterial values were estimated as MIC values. Fluconazole and ciprofloxacin [16 to 0.03 μg/mL] were used as the standard antifungal and antibacterial drug, respectively. Out of series of evaluated compounds, some of these compounds such as compounds 28, 29, 30, 31, 32, 33 have displayed maximum potency which is comparable to standard drugs.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S.J. Shaw, Mini Rev. Med. Chem., 8, 276 (2008); https://doi.org/10.2174/138955708783744137.
- D.K. Hutchinson, Curr. Top. Med. Chem., 3, 1021 (2003); https://doi.org/10.2174/1568026033452195.
- T. Asaka, A. Manaka and H. Sugiyama, Curr. Top. Med. Chem., 3, 961 (2003); https://doi.org/10.2174/1568026033452140.
- D. Sze, K. Miller and B. Neilan, Recent Patents Anticancer. Drug Discov., 3, 14 (2008); https://doi.org/10.2174/157489208783478685.
- D.J. Halls, Mikrochim. Acta, 57, 62 (1969); https://doi.org/10.1007/BF01216666.
- T.W. Greene and T.P.G.M. Wuts, Protective Group in Organic Synthesis. John Wiley & Sons, Inc.: New York, edn 4 (2007)
- P.J. Kociensiki, Protective Groups, Thieme-Verlag, Stuttgart, edn 3 (2003).
- J.P. Mayer, G.S. Lewis, M.J. Curtis and J. Zhang, Tetrahedron Lett., 38, 8445 (1997); https://doi.org/10.1016/S0040-4039(97)10276-3.
- H.P. Buchstaller, Tetrahedron, 54, 3465 (1998); https://doi.org/10.1016/S0040-4020(98)00079-9.
- P.T. Holte, L. Thijs and B. Zwanenburg, Tetrahedron Lett., 39, 7404 (1998); https://doi.org/10.1016/S0040-4039(98)01608-6.
- Y. Liu, K. Cui, W. Lu, W. Luo, J. Wang, J. Huang and C. Guo, Molecules, 16, 4527 (2011); https://doi.org/10.3390/molecules16064527.
- F. Ozkanli, A.G. Ozkanli, K. Ozadali, E. Yildirim and K. Erol, FABAD J. Pharm. Sci., 35, 19 (2010).
- L. Yurttas, Y. Özkay, M. Duran, G. Turan-Zitouni, A. Özdemir, Z. Cantürk, K. Küçükoglu and Z.A. Kaplancikli, Phosphorus Sulphur Silicon Rel. Elem., 191, 1166 (2016); https://doi.org/10.1080/10426507.2016.1150277.
- K.M. Heda and S.P. Deshmukh, Int. J. Chem. Sci., 9, 1705 (2011).
- K. Bacharaju, S.R. Jambula, S. Sivan, S.J. Tangeda and V. Manga, Bioorg. Med. Chem. Lett., 22, 3274 (2012); https://doi.org/10.1016/j.bmcl.2012.03.018.
- Y. Horita, T. Takii, R. Kuroishi, T. Chiba, K. Ogawa, L. Kremer, Y. Sato, Y.S. Lee, T. Hasegawa and K. Onozaki, Bioorg. Med. Chem., 21, 899 (2011); https://doi.org/10.1016/j.bmcl.2010.12.084.
- Y. Zou, S. Yu, R. Li, Q. Zhao, X. Li, M. Wu, T. Huang, X. Chai, H. Hu and Q. Wu, Eur. J. Med. Chem., 74, 366 (2014); https://doi.org/10.1016/j.ejmech.2014.01.009.
- S.L. Cao, Y. Wang, L. Zhu, J. Liao, Y.W. Guo, L.L. Chen, H.Q. Liu and X. Xu, Eur. J. Med. Chem., 45, 3850 (2010); https://doi.org/10.1016/j.ejmech.2010.05.038.
- M.A.-H. Zahran, T.A.-R. Salem, R.M. Samaka, H.S. Agwa and A.R. Awad, Bioorg. Med. Chem., 16, 9708 (2008); https://doi.org/10.1016/j.bmc.2008.09.071.
- J. Coro, R. Atherton, S. Little, H. Wharton, V. Yardley, A. Alvarez Jr., M. Suarez, R. Perez and H. Rodriguez, Bioorg. Med. Chem., 16, 1312 (2006); https://doi.org/10.1016/j.bmcl.2005.11.060.
- V. Marakov, O.B. Riabova, A. Yuschenko, N. Urlyapova, A. Daudova, P.F. Ziplef and U. Mollmann, J. Antimicrob. Chemother., 57, 1134 (2006); https://doi.org/10.1093/jac/dkl095.
- S.L. Cao, Y.P. Feng, X.L. Zheng, Y.Y. Jiang, M. Zhang, Y. Wang and M. Xu, Arch. Pharm. Chem. Life Sci., 339, 250 (2006); https://doi.org/10.1002/ardp.200500264.
- X. Hou, Z. Ge, T. Wang, W. Guo, J. Wu, J. Cui, C. Lai and R. Li, Arch. Pharm. Chem. Life Sci., 344, 320 (2011); https://doi.org/10.1002/ardp.201000259.
- A. Goel, S.J. Mazur, R.J. Fattah, T.L. Hartman, J.A. Turpin, M. Huang, W.G. Rice, E. Appella and J.K. Inman, Bioorg. Med. Chem. Lett., 12, 767 (2002); https://doi.org/10.1016/S0960-894X(02)00007-0.
- X.Y. He, L. Lu, J. Qiu, P. Zou, F. Yu, X.K. Jiang, L. Li, S. Jiang, S. Liu and L. Xie, Bioorg. Med. Chem., 21, 7539 (2013); https://doi.org/10.1016/j.bmc.2013.04.046.
- S.L. Cao, Y. Han, C.Z. Yuan, Y. Wang, Z.K. Xiahou, J. Liao, R.T. Gao, B.B. Mao, B.L. Zhao, Z.F. Li and X. Xu, Eur. J. Med. Chem., 64, 401 (2013); https://doi.org/10.1016/j.ejmech.2013.04.017.
- S. Jangir, V. Bala, N. Lal, L. Kumar, A. Sarswat, A. Kumar, Hamidullah, K.S. Saini, V. Sharma, V. Verma, J.P. Maikhuri, R. Konwar, G. Gupta and V.L. Sharma, Eur. J. Med. Chem., 85, 638 (2014); https://doi.org/10.1016/j.ejmech.2014.08.028.
- P. Liu, C. Li, J. Zhang and X. Xu, Synth. Commun., 43, 3342 (2013); https://doi.org/10.1080/00397911.2013.783600.
- A.Z. Halimehjani, Y. Pourshojaei and M.R. Saidi, Tetrahedron Lett., 50, 32 (2009); https://doi.org/10.1016/j.tetlet.2008.10.063.
- J. Jamir, U.B. Sinha, J. Nath and B.K. Patel, Synth. Commun., 42, 951 (2012); https://doi.org/10.1080/00397911.2010.532276.
- M. Kienle, A. Unsinn and P. Knochel, Angew. Chem. Int. Ed., 49, 4751 (2010); https://doi.org/10.1002/anie.201001025.
- V. Aucagne, C. Lorin, A. Tatibouet and P. Rollin, Tetrahedron Lett., 46, 4349 (2005); https://doi.org/10.1016/j.tetlet.2005.04.112.
- K. Alagiri and K.R. Prabhu, Chem. Eur. J., 17, 6922 (2011); https://doi.org/10.1002/chem.201100817.
- N.K. Kumar, K. Sreeramamurthy, S. Palle, K. Mukkanti and P. Das, Tetrahedron Lett., 51, 899 (2010); https://doi.org/10.1016/j.tetlet.2009.11.127.
- M.A. Khalilzadeh, Z. Hossaini, M.M. Baradarani and A. Hasannia, Tetrahedron Lett., 66, 8464 (2010); https://doi.org/10.1016/j.tet.2010.08.041.
- J.Y. Park, I.A. Ryu, H.H. Park, D.C. Ha and Y.D. Gong, Synthesis, 913 (2009); https://doi.org/10.1055/s-0028-1087970.
- D. Katiyar, V.K. Tiwari, R.P. Tripathi, A. Srivastava, V. Chaturvedi, R. Srivastava and B.S. Srivastava, Bioorg. Med. Chem., 11, 4369 (2003); https://doi.org/10.1016/S0968-0896(03)00480-2.
- P. Das, C.K. Kumar, N. Kumar, M. Innus, J. Iqbal and N. Srinivas, Tetrahedron Lett., 49, 992 (2008);
- U.A. Mohsen, Cukurova Med. J., 39, 729 (2014); https://doi.org/10.17826/cutf.79473.
- S.K. Tandel, S. Rajappa and S.V. Pansare, Tetrahedron, 49, 7479 (1993); https://doi.org/10.1016/S0040-4020(01)87224-0.
- F.R. Charati, Z. Hossaini and R. Hajinasiri, J. Appl. Chem. Res., 20, 54 (2012).
- L.J. Bahrin, P.J. Jones and H. Hopf, Beilstein J. Org. Chem., 8, 1999 (2012); https://doi.org/10.3762/bjoc.8.226.
- N.S. Gu¨nay, G. Capan, N. Ulusoy, N. Ergenc, G. Ötük and D. Kaya, Il Farmaco, 54, 826 (1999); https://doi.org/10.1016/S0014-827X(99)00109-3.
- K. Chauhan, M. Sharma, P. Singh, V. Kumar, P.K. Shukla, M.I. Siddiqi and P.M.S. Chauhan, MedChemComm, 3, 1104 (2012); https://doi.org/10.1039/c2md20109g.
- P.M. Madalageri and O. Kotresh, Der Pharm. Chem., 4, 2187 (2012).
- C. Donnici, L. Nogueira, M. Araujo, S. Oliveira, T. Magalhães, M. Lopes, A. Silva, A. Ferreira, C. Martins and M. de Resende Stoianoff, Molecules, 19, 5402 (2014); https://doi.org/10.3390/molecules19045402.
- E. Septolu, M.D. Aytemr, E. Killic, M. Ozalp and U. Califi, FABAD J. Pharm. Sci., 29, 1 (2004).
- D. Chaturvedi, S. Ray, A.K. Srivastava and R. Chander, Bioorg. Med. Chem., 16, 2489 (2008); https://doi.org/10.1016/j.bmc.2007.11.062.
References
S.J. Shaw, Mini Rev. Med. Chem., 8, 276 (2008); https://doi.org/10.2174/138955708783744137.
D.K. Hutchinson, Curr. Top. Med. Chem., 3, 1021 (2003); https://doi.org/10.2174/1568026033452195.
T. Asaka, A. Manaka and H. Sugiyama, Curr. Top. Med. Chem., 3, 961 (2003); https://doi.org/10.2174/1568026033452140.
D. Sze, K. Miller and B. Neilan, Recent Patents Anticancer. Drug Discov., 3, 14 (2008); https://doi.org/10.2174/157489208783478685.
D.J. Halls, Mikrochim. Acta, 57, 62 (1969); https://doi.org/10.1007/BF01216666.
T.W. Greene and T.P.G.M. Wuts, Protective Group in Organic Synthesis. John Wiley & Sons, Inc.: New York, edn 4 (2007)
P.J. Kociensiki, Protective Groups, Thieme-Verlag, Stuttgart, edn 3 (2003).
J.P. Mayer, G.S. Lewis, M.J. Curtis and J. Zhang, Tetrahedron Lett., 38, 8445 (1997); https://doi.org/10.1016/S0040-4039(97)10276-3.
H.P. Buchstaller, Tetrahedron, 54, 3465 (1998); https://doi.org/10.1016/S0040-4020(98)00079-9.
P.T. Holte, L. Thijs and B. Zwanenburg, Tetrahedron Lett., 39, 7404 (1998); https://doi.org/10.1016/S0040-4039(98)01608-6.
Y. Liu, K. Cui, W. Lu, W. Luo, J. Wang, J. Huang and C. Guo, Molecules, 16, 4527 (2011); https://doi.org/10.3390/molecules16064527.
F. Ozkanli, A.G. Ozkanli, K. Ozadali, E. Yildirim and K. Erol, FABAD J. Pharm. Sci., 35, 19 (2010).
L. Yurttas, Y. Özkay, M. Duran, G. Turan-Zitouni, A. Özdemir, Z. Cantürk, K. Küçükoglu and Z.A. Kaplancikli, Phosphorus Sulphur Silicon Rel. Elem., 191, 1166 (2016); https://doi.org/10.1080/10426507.2016.1150277.
K.M. Heda and S.P. Deshmukh, Int. J. Chem. Sci., 9, 1705 (2011).
K. Bacharaju, S.R. Jambula, S. Sivan, S.J. Tangeda and V. Manga, Bioorg. Med. Chem. Lett., 22, 3274 (2012); https://doi.org/10.1016/j.bmcl.2012.03.018.
Y. Horita, T. Takii, R. Kuroishi, T. Chiba, K. Ogawa, L. Kremer, Y. Sato, Y.S. Lee, T. Hasegawa and K. Onozaki, Bioorg. Med. Chem., 21, 899 (2011); https://doi.org/10.1016/j.bmcl.2010.12.084.
Y. Zou, S. Yu, R. Li, Q. Zhao, X. Li, M. Wu, T. Huang, X. Chai, H. Hu and Q. Wu, Eur. J. Med. Chem., 74, 366 (2014); https://doi.org/10.1016/j.ejmech.2014.01.009.
S.L. Cao, Y. Wang, L. Zhu, J. Liao, Y.W. Guo, L.L. Chen, H.Q. Liu and X. Xu, Eur. J. Med. Chem., 45, 3850 (2010); https://doi.org/10.1016/j.ejmech.2010.05.038.
M.A.-H. Zahran, T.A.-R. Salem, R.M. Samaka, H.S. Agwa and A.R. Awad, Bioorg. Med. Chem., 16, 9708 (2008); https://doi.org/10.1016/j.bmc.2008.09.071.
J. Coro, R. Atherton, S. Little, H. Wharton, V. Yardley, A. Alvarez Jr., M. Suarez, R. Perez and H. Rodriguez, Bioorg. Med. Chem., 16, 1312 (2006); https://doi.org/10.1016/j.bmcl.2005.11.060.
V. Marakov, O.B. Riabova, A. Yuschenko, N. Urlyapova, A. Daudova, P.F. Ziplef and U. Mollmann, J. Antimicrob. Chemother., 57, 1134 (2006); https://doi.org/10.1093/jac/dkl095.
S.L. Cao, Y.P. Feng, X.L. Zheng, Y.Y. Jiang, M. Zhang, Y. Wang and M. Xu, Arch. Pharm. Chem. Life Sci., 339, 250 (2006); https://doi.org/10.1002/ardp.200500264.
X. Hou, Z. Ge, T. Wang, W. Guo, J. Wu, J. Cui, C. Lai and R. Li, Arch. Pharm. Chem. Life Sci., 344, 320 (2011); https://doi.org/10.1002/ardp.201000259.
A. Goel, S.J. Mazur, R.J. Fattah, T.L. Hartman, J.A. Turpin, M. Huang, W.G. Rice, E. Appella and J.K. Inman, Bioorg. Med. Chem. Lett., 12, 767 (2002); https://doi.org/10.1016/S0960-894X(02)00007-0.
X.Y. He, L. Lu, J. Qiu, P. Zou, F. Yu, X.K. Jiang, L. Li, S. Jiang, S. Liu and L. Xie, Bioorg. Med. Chem., 21, 7539 (2013); https://doi.org/10.1016/j.bmc.2013.04.046.
S.L. Cao, Y. Han, C.Z. Yuan, Y. Wang, Z.K. Xiahou, J. Liao, R.T. Gao, B.B. Mao, B.L. Zhao, Z.F. Li and X. Xu, Eur. J. Med. Chem., 64, 401 (2013); https://doi.org/10.1016/j.ejmech.2013.04.017.
S. Jangir, V. Bala, N. Lal, L. Kumar, A. Sarswat, A. Kumar, Hamidullah, K.S. Saini, V. Sharma, V. Verma, J.P. Maikhuri, R. Konwar, G. Gupta and V.L. Sharma, Eur. J. Med. Chem., 85, 638 (2014); https://doi.org/10.1016/j.ejmech.2014.08.028.
P. Liu, C. Li, J. Zhang and X. Xu, Synth. Commun., 43, 3342 (2013); https://doi.org/10.1080/00397911.2013.783600.
A.Z. Halimehjani, Y. Pourshojaei and M.R. Saidi, Tetrahedron Lett., 50, 32 (2009); https://doi.org/10.1016/j.tetlet.2008.10.063.
J. Jamir, U.B. Sinha, J. Nath and B.K. Patel, Synth. Commun., 42, 951 (2012); https://doi.org/10.1080/00397911.2010.532276.
M. Kienle, A. Unsinn and P. Knochel, Angew. Chem. Int. Ed., 49, 4751 (2010); https://doi.org/10.1002/anie.201001025.
V. Aucagne, C. Lorin, A. Tatibouet and P. Rollin, Tetrahedron Lett., 46, 4349 (2005); https://doi.org/10.1016/j.tetlet.2005.04.112.
K. Alagiri and K.R. Prabhu, Chem. Eur. J., 17, 6922 (2011); https://doi.org/10.1002/chem.201100817.
N.K. Kumar, K. Sreeramamurthy, S. Palle, K. Mukkanti and P. Das, Tetrahedron Lett., 51, 899 (2010); https://doi.org/10.1016/j.tetlet.2009.11.127.
M.A. Khalilzadeh, Z. Hossaini, M.M. Baradarani and A. Hasannia, Tetrahedron Lett., 66, 8464 (2010); https://doi.org/10.1016/j.tet.2010.08.041.
J.Y. Park, I.A. Ryu, H.H. Park, D.C. Ha and Y.D. Gong, Synthesis, 913 (2009); https://doi.org/10.1055/s-0028-1087970.
D. Katiyar, V.K. Tiwari, R.P. Tripathi, A. Srivastava, V. Chaturvedi, R. Srivastava and B.S. Srivastava, Bioorg. Med. Chem., 11, 4369 (2003); https://doi.org/10.1016/S0968-0896(03)00480-2.
P. Das, C.K. Kumar, N. Kumar, M. Innus, J. Iqbal and N. Srinivas, Tetrahedron Lett., 49, 992 (2008);
U.A. Mohsen, Cukurova Med. J., 39, 729 (2014); https://doi.org/10.17826/cutf.79473.
S.K. Tandel, S. Rajappa and S.V. Pansare, Tetrahedron, 49, 7479 (1993); https://doi.org/10.1016/S0040-4020(01)87224-0.
F.R. Charati, Z. Hossaini and R. Hajinasiri, J. Appl. Chem. Res., 20, 54 (2012).
L.J. Bahrin, P.J. Jones and H. Hopf, Beilstein J. Org. Chem., 8, 1999 (2012); https://doi.org/10.3762/bjoc.8.226.
N.S. Gu¨nay, G. Capan, N. Ulusoy, N. Ergenc, G. Ötük and D. Kaya, Il Farmaco, 54, 826 (1999); https://doi.org/10.1016/S0014-827X(99)00109-3.
K. Chauhan, M. Sharma, P. Singh, V. Kumar, P.K. Shukla, M.I. Siddiqi and P.M.S. Chauhan, MedChemComm, 3, 1104 (2012); https://doi.org/10.1039/c2md20109g.
P.M. Madalageri and O. Kotresh, Der Pharm. Chem., 4, 2187 (2012).
C. Donnici, L. Nogueira, M. Araujo, S. Oliveira, T. Magalhães, M. Lopes, A. Silva, A. Ferreira, C. Martins and M. de Resende Stoianoff, Molecules, 19, 5402 (2014); https://doi.org/10.3390/molecules19045402.
E. Septolu, M.D. Aytemr, E. Killic, M. Ozalp and U. Califi, FABAD J. Pharm. Sci., 29, 1 (2004).
D. Chaturvedi, S. Ray, A.K. Srivastava and R. Chander, Bioorg. Med. Chem., 16, 2489 (2008); https://doi.org/10.1016/j.bmc.2007.11.062.