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Synthesis, Characterization, Stereochemistry and Biological Evaluation of Novel Cyclohexanol Derivatives
Corresponding Author(s) : Sayeed Mukhtar
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
This research includes the synthesis of 1,5-diketone from chalcone by Michael addition of p-chloroacetophenone in the presence of NaOH (molar ratio, 1:1:10), which led to the formation of a novel cyclohexanol derivative as a side product. The above reaction was repeated with different molar ratio of chalcone-acetophenone-sodium hydroxide to set the optimum condition for maximum yield of the novel cyclohexanol derivative. The dehydration of cyclohexanol using catalytic amount of p-TsOH produced quantitative yield of corresponding cyclohexene with β,γ-unsaturation instead of apparently more stable α,β-unsaturation. The compounds were well characterized by spectroscopic techniques and elemental analysis. Their stereochemistry is discussed and newly synthesized compounds are screened for anticancer and antimicrobial activities.
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- J. Barluenga, L. Alvarez-Rodrigo, F. Rodriguez, F. Fananas, T. Sordo and P. Campomanes, Angew. Chem. Int. Ed., 46, 2607 (2007); https://doi.org/10.1002/anie.200605172.
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- S. Pandey, S. Singh, B. Patro and A. Ghosh, Indian J. Chem., 43B, 2705 (2004).
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- D.C. Kosegarten, J.J. Defeo and D.R. DeFanti, J. Pharm. Sci., 56, 1104 (1967); https://doi.org/10.1002/jps.2600560911.
- V. Mahyavanshi, S.I. Marjadi and R. Yadav, Arab. J. Chem., 10, S804 (2017); https://doi.org/10.1016/j.arabjc.2012.12.009.
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- H. Parveen, R.A.S. Alatawi, N.H. El Sayed, S. Hasan, S. Mukhtar and A.U. Khan, Arab. J. Chem., 10, 1098 (2017); https://doi.org/10.1016/j.arabjc.2015.05.002.
- S. Mukhtar, M.I. Al-Ahmdi and H. Parveen, Asian J. Chem., 28, 2589 (2016); https://doi.org/10.14233/ajchem.2016.19908.
- K. Salat, A. Moniczewski and T. Librowski, Mini Rev. Med. Chem., 13, 335 (2013); https://doi.org/10.2174/1389557511313030003.
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- V.P.M. Rahman, S. Mukhtar, W.H. Ansari and G. Lemiere, Eur. J. Med. Chem., 40, 173 (2005); https://doi.org/10.1016/j.ejmech.2004.10.003.
- S. Mukhtar, M. Rahman, W. Ansari, G. Lemière, A. De Groot and R. Dommisse, Molecules, 4, 232 (1999); https://doi.org/10.3390/40700232.
- G.D. Gray and E. Wickstrom, Biotechniques, 21, 780 (1996).
- C. Perez, M. Pauli and P. Bazerque, Acta Biol. Exp., 15, 113 (1990).
- A.Z. Beg and I. Ahmad, World J. Microbiol. Biotechnol., 16, 841 (2000); https://doi.org/10.1023/A:1008991724288.
- A. Lubineau and J. Auge, Tetrahedron Lett., 33, 8073 (1992); https://doi.org/10.1016/S0040-4039(00)74720-4.
- R. Antonioletti, F. Bonadies, E.S. Monteagudo and A. Scettri, Tetrahedron Lett., 32, 5373 (1991); https://doi.org/10.1016/S0040-4039(00)92389-X.
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References
J. Barluenga, L. Alvarez-Rodrigo, F. Rodriguez, F. Fananas, T. Sordo and P. Campomanes, Angew. Chem. Int. Ed., 46, 2607 (2007); https://doi.org/10.1002/anie.200605172.
G. Lu and C. Cai, J. Chem. Res., 35, 147 (2011); https://doi.org/10.3184/174751911X12977065405044.
I. Mamedov, R. Abbasoglu, M. Bayramov and A. Maharramov, Magn. Reson. Chem., 54, 315 (2016); https://doi.org/10.1002/mrc.4377.
Y. Obata, C. Jie Li, M. Fujikawa, K. Takayama, H. Sato, K. Higashiyama, K. Isowa and T. Nagai, Int. J. Pharm., 212, 223 (2001); https://doi.org/10.1016/S0378-5173(00)00608-6.
S. Pandey, S. Singh, B. Patro and A. Ghosh, Indian J. Chem., 43B, 2705 (2004).
L. Rong, X. Wei, Y. Lu and Z. Zong, Youji Huaxue, 32, 1999 (2012); https://doi.org/10.6023/cjoc201204004.
G. Rogers, S. Parsons, D. Anderson, L. Nilsson, B. Bahr, W. Kornreich, R. Kaufman, R. Jacobs and B. Kirtman, J. Med. Chem., 32, 1217 (1989); https://doi.org/10.1021/jm00126a013.
K. Anan, M. Masui, S. Hara, M. Ohara, M. Kume, S. Yamamoto, S. Shinohara, H. Tsuji, S. Shimada, S. Yagi, N. Hasebe and H. Kai, Bioorg. Med. Chem. Lett., 27, 4194 (2017); https://doi.org/10.1016/j.bmcl.2017.06.076.
A. Dhir, S. Malik, S.V. Kessar, K.N. Singh and S.K. Kulkarni, Eur. Neuropsychopharmacol., 21, 705 (2011); https://doi.org/10.1016/j.euroneuro.2010.12.003.
D.C. Kosegarten, J.J. Defeo and D.R. DeFanti, J. Pharm. Sci., 56, 1104 (1967); https://doi.org/10.1002/jps.2600560911.
V. Mahyavanshi, S.I. Marjadi and R. Yadav, Arab. J. Chem., 10, S804 (2017); https://doi.org/10.1016/j.arabjc.2012.12.009.
H. Parveen, F. Hayat, S. Mukhtar, A. Salahuddin, A. Khan, F. Islam and A. Azam, Eur. J. Med. Chem., 46, 4669 (2011); https://doi.org/10.1016/j.ejmech.2011.05.055.
H. Parveen, S. Mukhtar and A. Azam, J. Heterocycl. Chem., 53, 473 (2016); https://doi.org/10.1002/jhet.2427.
H. Parveen, R.A.S. Alatawi, N.H. El Sayed, S. Hasan, S. Mukhtar and A.U. Khan, Arab. J. Chem., 10, 1098 (2017); https://doi.org/10.1016/j.arabjc.2015.05.002.
S. Mukhtar, M.I. Al-Ahmdi and H. Parveen, Asian J. Chem., 28, 2589 (2016); https://doi.org/10.14233/ajchem.2016.19908.
K. Salat, A. Moniczewski and T. Librowski, Mini Rev. Med. Chem., 13, 335 (2013); https://doi.org/10.2174/1389557511313030003.
T. Torroba, J. Prakt. Chem., 341, 99 (1999); https://doi.org/10.1002/(SICI)1521-3897(199902)341:2<99::AIDPRAC99>3.0.CO;2-Z.
V.P.M. Rahman, S. Mukhtar, W.H. Ansari and G. Lemiere, Eur. J. Med. Chem., 40, 173 (2005); https://doi.org/10.1016/j.ejmech.2004.10.003.
S. Mukhtar, M. Rahman, W. Ansari, G. Lemière, A. De Groot and R. Dommisse, Molecules, 4, 232 (1999); https://doi.org/10.3390/40700232.
G.D. Gray and E. Wickstrom, Biotechniques, 21, 780 (1996).
C. Perez, M. Pauli and P. Bazerque, Acta Biol. Exp., 15, 113 (1990).
A.Z. Beg and I. Ahmad, World J. Microbiol. Biotechnol., 16, 841 (2000); https://doi.org/10.1023/A:1008991724288.
A. Lubineau and J. Auge, Tetrahedron Lett., 33, 8073 (1992); https://doi.org/10.1016/S0040-4039(00)74720-4.
R. Antonioletti, F. Bonadies, E.S. Monteagudo and A. Scettri, Tetrahedron Lett., 32, 5373 (1991); https://doi.org/10.1016/S0040-4039(00)92389-X.
J. March, Advanced Organic Chemistry, John Wiley & Sons, edn 4, p. 1009 (1992).
M. Weiss, J. Am. Chem. Soc., 74, 200 (1952); https://doi.org/10.1021/ja01121a051.
F. Krohnke, Synthesis, 1 (1976); https://doi.org/10.1055/s-1976-23941.