Abstract
A series of bis heterocycles comprising both piperidine and thiohydantoin nuclei namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones is synthesized and characterized by melting point, elemental analysis, MS, FT–IR, one-dimensional NMR (1H, D2O exchanged 1H and 13C), two-dimensional HOMOCOSY, and NOESY spectroscopic data.
Graphical Abstract
Similar content being viewed by others
References
C.R. Noller, V. Baliah, J. Am. Chem. Soc. 70, 3853 (1948)
V. Baliah, R. Jeyaraman, L. Chandrasekaran, Chem. Rev. 83, 379 (1983)
W. Lijinsky, H. Taylor, Int. J. Cancer 16, 318 (1975)
H.I. El-Subbagh, S.M. Abu-Zaid, M.A. Mahran, F.A. Badria, A.M. Alofaid, J. Med. Chem. 43, 2915 (2000)
A.A. Watson, G.W.J. Fleet, N. Asano, R.J. Molyneux, R.J. Nugh, Phytochemistry 56, 265 (2001)
C.R. Ganellin, R.G. Spickett, J. Med. Chem. 8, 619 (1965)
R.E. Hagenbach, H. Gysin, Experimentia 8, 184 (1952)
B. Ileana, V. Dobre, I. Nicluescu-Duvaz, J. Prakt. Chem. 327, 667 (1985)
I.G. Mokio, A.T. Soldatenkov, V.O. Federov, E.A. Ageev, N.D. Sergeeva, S. Lin, E.E. Stashenku, N.S. Prostakov, E.I. Andreeva, Khim. Farm. Zh. 23, 421 (1989)
J.R. Dimmock, P. Kumar, Curr. Med. Chem. 4, 1 (1997)
H. Kubota, A. Kakefuda, Y. Okamoto, M. Fujii, O. Yamamoto, Y. Yamgiwa, M. Orita, K. Ikeda, M. Takenchi, T. Shibanuma, Y. Fsomura, Chem. Pharm. Bull. 46, 1538 (1998)
T.B. Johnson, L.H. Chernoff, J. Am. Chem. Soc. 35, 1208 (1913)
J.E. Tompkins, J. Med. Chem. 29, 855 (1986)
A.M. Al-Obaid, H.I. El-Subbagh, A.I. Khodair, M.M. Elmazar, Anticancer Drugs 7, 873 (1996)
E. Froelich, A. Fruehan, M. Jackman, F.K. Kirchner, E.J. Alexander, S. Archer, J Am. Chem.Soc. 76, 3099 (1954)
J.V. Marx, D.A. Richert, W.W. Westerfeld, J. Med. Chem. 13, 1179 (1970)
A.A. El-Barbary, A.I. Khodair, E.B. Pedersen, C. Nielsen, J. Med. Chem. 37, 73 (1994)
J.R. Chérouvrier, F. Carreaux, J.P. Bazureau, Molecules 9, 867 (2004)
S. Archer, M.J. Unser, E. Froelich, J. Am. Chem. Soc. 78, 6182 (1956)
J. Marton, J. Enisz, S. Hosztafi, T. Timar, J. Agric. Food Chem. 41, 148 (1993)
A.C.W. Curran, U.S. Patent 3984430, 1976
K.L. Nagpal, U.S. Patent 4473393, 1984
L.D. Cromwellt, G.R. Stark, Biochemistry 8, 4735 (1969)
J.V. Nelson, M.J. Helber, M. Brick, U.S. Patent 5695917, 1997
S.S. Kandil, G.B. El-Hefnawy, E.A. Baker, Thermochim. Acta 414, 105 (2004)
M. Gopalakrishnan, P. Sureshkumar, J. Thanusu, C. Prabhu, V. Kanagarajan, J. Chem Res 2, 80 (2007)
M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, R. Govindaraju, J Chem. Res. 5, 299 (2005)
M. Gopalakrishnan, J. Thanusu, V. Kanagarajan, J. of Korean Chem. Soc. 52, 47 (2008)
M. Gopalakrishnan, V. Kanagarajan, J. Thanusu, Green Chem. Lett. 1, 241 (2008)
M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, J. Korean Chem. Soc. 51, 346 (2007)
M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, Lett. Org. Chem. 2, 444 (2005)
M. Gopalakrishnan, P. Sureshkumar, J. Thanusu, V. Kanagarajan, R. Govindaraju, M.R. Ezhilarasi, Lett. Org. Chem. 6, 484 (2006)
M. Gopalakrishnan, P. Sureshkumar, J. Thanusu, V. Kanagarajan, Chem. Heterocycl. Comp. 44, 950 (2008)
J. Thanusu, V. Kanagarajan, M. Gopalakrishnan, Bioorg. Med. Chem. Lett. 20, 713 (2010)
Acknowledgments
The authors are thankful to NMR Research Centre, Indian Institute of Science, Bangalore, for recording spectra. One of the authors, V. Kanagarajan, is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for providing financial support in the form of a CSIR-Senior Research Fellowship (SRF) in Organic Chemistry. Another author, J. Thanusu, is highly thankful to Annamalai University authorities for providing a University Fellowship.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Thanusu, J., Kanagarajan, V. & Gopalakrishnan, M. Spectral characterization of novel bis heterocycles comprising both piperidine and thiohydantoin nuclei. Res Chem Intermed 36, 1073–1084 (2010). https://doi.org/10.1007/s11164-010-0221-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-010-0221-7