Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Novel Synthetic Strategy of Cyclic Dithiocarbamates Catalyzed by Triton-B
Corresponding Author(s) : M. Kamboj
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
A simple, rapid and green methodology to synthesize cyclic dithiocarbamates (compounds 1-9) was developed by the reaction of 1° amines, CS2 and ethyl 3-bromo-2-oxopropanoate (ethyl bromopyruvate) facilitated by Triton-B as phase transfer catalyst. These compounds (1-9) were characterized with the help of elemental analysis, IR, NMR and mass spectroscopic methods This efficient green approach requires mild conditions and gives good yield of product. In vitro antimicrobial activities of these compounds are reported against the pathogenic bacteria and fungi.
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- S.L. Cao, Y. Han, C.Z. Yuan, Y. Wang, J.K. Xiahou, J. Liao, R.T. Gao, B.B. Mao, B.L. Zhao, J.F. Li and X. Xu, Eur. J. Med. Chem., 64, 401 (2013); https://doi.org/10.1016/j.ejmech.2013.04.017.
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- K. Venugopal, A. Jayaraju and J. Sreeramulu, J. Pharm. Res., 9, 125 (2015).
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- 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, J. 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.
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- M. Ertan, A.A. Bilgin, E. Palaska and N. Yulug, Arzneimittelforschung, 42, 160 (1992).
References
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B. Cvek and Z. Dvorak, Curr. Pharm. Des., 13, 3155 (2007); https://doi.org/10.2174/138161207782110390.
O. Guzel and A. Salman, Bioorg. Med. Chem., 14, 7804 (2006); https://doi.org/10.1016/j.bmc.2006.07.065.
Y. Qian, J.Y. Ma, Y. Yang, K. Cheng, Q.Z. Zheng, W.J. Mao, L. Shi, J. Zhao and H.L. Zhu, Bioorg. Med. Chem., 18, 4310 (2010); https://doi.org/10.1016/j.bmc.2010.04.091.
S. Senkbeil, J.P. Lafleur, T.G. Jensen and J.P. Kutter, In Proceedings of 16th International Conference on Miniaturized Systems for Chemistry and Life Sciences, Japan, pp. 1423-1425 (2012).
I. Rogachev, V. Kampel, V. Gusis, N. Cohen, J. Gressel and A. Warshawsky, Pestic. Biochem. Physiol., 60, 133 (1998); https://doi.org/10.1006/pest.1998.2336.
G. Eng, X. Song, Q. Duong, D. Strickman, J. Glass and L. May, Appl. Organomet. Chem., 17, 218 (2003); https://doi.org/10.1002/aoc.423.
C. Lamberth, J. Sulphur Chem., 25, 39 (2004); https://doi.org/10.1080/17415990310001612290.
R.S. Grainger and P. Innocenti, Heteroatom Chem., 18, 568 (2007); https://doi.org/10.1002/hc.20336.
K. Venugopal, A. Jayaraju and J. Sreeramulu, J. Pharm. Res., 9, 125 (2015).
P. Morf, F. Raimondi, H.G. Nothofer, B. Schnyder, A. Yasuda, J.M. Wessels and T.A. Jung, Langmuir, 22, 658 (2006); https://doi.org/10.1021/la052952u.
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M.A. Haendel, F. Tilton, G.S. Bailey and R.L. Tanguay, Toxicol. Sci., 81, 390 (2004); https://doi.org/10.1093/toxsci/kfh202.
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U.A. Mohsen, Cukurova Med. J., 39, 729 (2014); https://doi.org/10.17826/cutf.79473.
S. Jangir, V. Bala, N. Lal, L. Kumar, A. Sarswat, A. Kumar, K.S. 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.
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P. Liu, C. Li, J. Zhang and X. Xu, Synth. Commun., 43, 3342 (2013); https://doi.org/10.1080/00397911.2013.783600.
A.J. Halimehjani, J. 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.
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.
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, J. 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.
P.M. Madalageri and O. Kotresh, J. Chem. Pharm. Res., 4, 2697 (2012).
R.B. Silverman, The Organic Chemistry of Drug Design and Drug Action, Elsevier Academic Press: Burlington, USA, Chap. 2 (2004).
H. Waterbeemd and R. Mannhold, Lipophilicity in Drug Action and Toxicology, VCH Publishers: NewYork Chap. 23 (1996).
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei and M.R. Saidi, J. Org. Chem., 71, 3634 (2006); https://doi.org/10.1021/jo060048g.
K. Bacharaju, S.R. Jambula, S. Sivan, S. Jyostnatangeda and V. Manga, Bioorg. Med. Chem. Lett., 22, 3274 (2012); https://doi.org/10.1016/j.bmcl.2012.03.018.
M.E. Mulkey, The Grouping of a Series of Dithiocarbamate Pesticides Based on a Common Mechanism of Toxicity; US Environmental Protection Agency, Office of Pesticide Programs, Office of Prevention, Pesticides and Toxic Substances, Washington, DC; SAP Report No. 2001, FIFRA Scientific Advisory Panel Meeting, September 7, 2001, Sheraton Crystal City Hotel, Arlington, Wastington DC., USA, p. 1 (2001).
D. Chaturvedi, S. Zaidi, A.K. Chaturvedi, S. Vaid and A.K. Saxena, Indian J. Chem., 55B, 1019 (2016).
J. Garin, E. Meléndez, F.L. Merchán, T. Tejero, S. Uriel and J. Ayestarán, Synthesis, 147 (1991); https://doi.org/10.1055/s-1991-26400.
J.M. Andrews, J. Antimicrob. Chemother., 48(Suppl_1), 5 (2001); https://doi.org/10.1093/jac/48.suppl_1.5.
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.
R. Kishore and M. Kamboj, World J. Pharm. Res., 7, 1098 (2018).
S. Zaidi, A.K. Chaturvedi, N. Singh and D. Chaturvedi, Curr. Chem. Lett., 6, 143 (2017); https://doi.org/10.5267/j.ccl.2017.7.001.
M. Ertan, A.A. Bilgin, E. Palaska and N. Yulug, Arzneimittelforschung, 42, 160 (1992).