Abstract
The regularities of the reduction of unsaturated nitriles containing the 2-adamantyl fragment with lithium aluminum hydride and nickel—aluminum alloy were studied. In both cases, the double bond and nitrile group were simultaneously reduced. The presence of bulky substituents in the substrate in the α-position to the adamantyl fragment and hydroxy groups significantly retards the process, and the 80–90% yield of the corresponding products is achieved only when the temperature is raised to 65 °C. In the case of using a nickel—aluminum alloy, its 4—6-fold excess is required. The calculation of the potential pharmacological activity of the synthesized compounds shows that they can have antiviral, analgesic, and antidiabetic activity.
This is a preview of subscription content, log in via an institution to check access.
References
I. S. Morozov, V. I. Petrov, S. A. Sergeeva, Farmakologiya adamantanov [Pharmacology of Adamantanes], Volgograd Medical Academy, Volgograd, 2001, 320 pp. (in Russian).
I. A. Novakov, B. S. Orlinson, D. V. Zavyalov, S. V. Mednikov, E. N. Savelyev, E. A. Potayenkova, M. A. Nakhod, A. M. Pichugin, A. V. Kireeva, M. N. Kovaleva, Russ. Chem. Bull., 2021, 6, 1141–1148; DOI: https://doi.org/10.1007/s11172-021-3196-1.
B. Gopalan, T. Ponpandian, V. Kachhadia, K. Bharathimohan, R. Vignesh, V. Sivasudar, S. Narayanan, B. Mandar, R. Praveen, N. Saranya, S. Rajagopal, S. Rajagopal, Bioorganic Medicinal Chemistry Letters, 2013, 23, 2532–2537; DOI: https://doi.org/10.1016/j.bmcl.2013.03.002.
US Pat. EP1305306B1; National Center for Biotechnology Information, 2005, 48, 01951817.4.
X. Su, N. Vicker, M. Trusselle, H. Halem, M.D. Culler, B.V. Potter, Molecular and Cellular Endocrinology, 2009, 301, No. 1–2, 169–173; DOI: https://doi.org/10.1016/j.mce.2008.08.006.
N. Kolocouris, A. Kolocouris, G. B. Foscolos, G. Fytas, J. Neyts, E. Padalko, E. De Clercq, J. Med. Chemistry, 1996, 39, No. 17, 3307–3318; DOI: https://doi.org/10.1021/jm950891z.
J. Seyden-Penne, Reductions by Alumino and Borohydrides in Organic Synthesis, Wiley-VCH, New York, 1997, 1.
S. X. Liu, Y. H. Yang, X. L. Zhen, J. Z. Li, H. M. He, J. Feng, A. Whiting, Org. Biomol.Chem., 2012, 10, 663–670; DOI: https://doi.org/10.1039/c1ob06471a.
S. Laval, W. Dayoub, A. Favre-Reguillon, M. Berthod, P. Demonchaux, M. Lemaire, Tetrahedron Lett., 2009, 50, 7005–7007; DOI: https://doi.org/10.1016/j.tetlet.2009.09.164.
S. Caddick, D. B. Judd, A. K. K. de Lewis, M. T. Reich, M. R. V. Williams, Tetrahedron Lett., 2003, 59, 5417–5423; DOI: https://doi.org/10.1016/S0040-4020(03)00858-5.
Ch. Bornschein, S. Werkmeister, B. Wendt, H. Jiao, E. Alberico, W. Baumann, H. Junge, K. Junge, M. Beller, Nature Common., 2014, 5, 4111–4122; DOI: https://doi.org/10.1038/ncomms5111.
D. Haddenham, L. Pasumansky, J. De Soto, S. Eagon, B. Singaram, J. Org. Chem., 2009, 74, 1964–1970; DOI: https://doi.org/10.1021/jo8023329.
Yu. V. Popov, V. M. Mokhov, N. A. Tankabekyan, E. Yu. Uzakov, Izv. Volg. GTU, Ser. Khimiya i tekhnologiya elementoorganicheskikh monomerov o polimernykh materialov [Bulletin of Volgograd State Technical University, Ser. Chemistry and Technology of Organoelement Monomers and Polymer Materials], 2011, 2, 29–32 (in Russian).
M. Yu. Skomorokhov, M. V. Leonova, A. K. Shiryaev, Yu. N. Klimochkin, Russ. J. Org. Chem., 2003, 39, 1360–1361; DOI: https://doi.org/10.1023/B:RUJO.0000010230.77371.3b.
V. V. Burmistrov, V. S. D’yachenko, D. A. Pitushkin, E. V. Rasskazova, V. V. Ikryannikova, G. M. Butov, E. N. Savel’ev, B. S. Orlinson, I. A. Novakov, Izv. Volg. GTU, Ser. Khimiya i tekhnologiya elementoorganicheskikh monomerov o polimernykh materialov [Bulletin of Volgograd State Technical University, Ser. Chemistry and Technology of Organoelement Monomers and Polymer Materials], 2018, 4, 39–43 (in Russian).
F. David, Organic Process Research & Development, 2007, 11, 156–159; DOI: https://doi.org/10.1021/op060155c.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2720–2729, December, 2022.
The studies were carried out using the equipment of the Center for Collective Use «Physicochemical Investigation Methods» at the Vogograd State Technical University.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Novakov, I.A., Orlinson, B.S., Savel’ev, E.N. et al. Synthesis of 2-adamantyl-containing amines as compounds with potential pharmacological activity. Russ Chem Bull 71, 2720–2729 (2022). https://doi.org/10.1007/s11172-022-3701-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-022-3701-1