Abstract
A series of mono-, bis-, and tris-substituted lactamomethyl derivatives of diphenols were synthesized. The solution and solid-state structures of these compounds were confirmed by IR and NMR spectroscopy and X-ray diffraction. The in silico evaluation indicated a high probability that these compounds have various biological activities.
Similar content being viewed by others
References
M. C. van der Goes, J. W. Jacobs, J. W. Blsma, Arthritis Res. Ther., 2014, 16, 2.
M. Moini, M. L. Schilsky, E. M. Tichy, World J. Hepatol, 2015, 7, 1355.
J. V. Formica, W. Regelson, Fd. Chem. Toxic., 1995, 33, 1061.aaaa
E. H. Kelly, R. T. Anthony, J. B. Dennis, J. Nutr. Biochem., 2002, 13, 572.
A. K. Pandey, A. K. Mishra, A. Mishra, S. Kumar, A. Chandra, Int. J. Biol. Med. Res., 2010, 1, 228.
Yu. O. Teselkin, B. A. Zhambalova, I. V. Babenkova, G. I. Klebanov, N. A. Tyukavkina, Biophysics, 1996, 41. No 3, 620.
K. Zandi, B. T. Teoh, S. S. Sam, P. F. Wong, M. R. Mustafa, S. Abubakar, Virology J., 2011, 8, 560.
T. Mahendra, Y. Kim, J. Desper, K.-O. Chang, D. H. Hua, Bioorg. Med. Chem. Lett., 2012, 22, 353.
W. Zhu, Q. Jia, Y. Wang, Y. Zhang, M. Xia, Free Radical Biol. Med., 2012, 52. No 2, 314.
Q. He, J. Kim, R. P. Sharma, Toxicol. Sci., 2004, 80. No 2, 335.
E. E. Nifantév, S. E. Mosyurov, T. S. Kukhareva, L. K. Vasya nina, Dokl. Chem., 2013, 451, 197.
V. S. Rogovskii, A. I. Matyushin, N. L. Shimanovskii, A. V. Semeikin, T. S. Kukhareva, A. M. Koroteev, M. P. Koroteev, E. E. Nifantév, Eksp. Klinich/Farmakol. [Russ. J. Exp. Clin. Pharmacol.]. 2010, No. 9, 39 (in Russian).
A. V. Kadushkin, T. V. Golovko, V. G. Granik, R. G. Glushkov, R. B. Parimbetova, V. A. Parshin, M. D. Mashkovskii, Pharm. Chem. J., 1989, 23, 1301.
R. U. Ostrovskaya, S. S. Trofimov, Yu. V. Burov, Pharm. Chem. J., 1993, 27, 13.
F. Foubelo, M. Yus, Russ. Chem. Bull., 2016, 65, 1667].
V. V. Negrebetskii, O. N. Chupakhin, A. A. Korlyukov, M. A. Kuznetsov, L. Ya. Zakharova, A. I. Konovalov, O. N. Burov, A. Yu. Egorova, S. E. Solovéva, A. V. Kolobov, A. V. Vasilév, I. G. Zenkevich, V. Yu. Orlov, A. V. Aksenov, D. N. Kuznetsov, K. I. Kobrakov, O. A. Golubchikov, V. A. Nikolaev, S. Z. Vatsadze, I. P. Beletskaya, A. Yu. Fedorov, V. N. Charushin, V. A. Osyanin, Yu. N. Klimochkin, A. T. Lebedev, O. G. Sinyashin, D. A. Lemenovskii, A. I. Rusakov, A. S. Tikhomirov, G. A. Suboch, T. I. Madzhidov, S. P. Gromov, A. E. Shchekotikhin, I. S. Antipin, R. S. Begunov, M. P. Koroteev, M. S. Tovbis, I. I. Stoikov, A. P. Molchanov, M. S. Novikov, A. F. Khlebnikov, V. G. Nenaidenko, M. E. Kletskii, A. N. Reznikov, V. S. Petrosyan, M. K. Grachev, V. I. Maslennikova, S. V. Kurbatov, S. M. Ivanov, L. M. Mironovich, A. V. Nemtarev, F. I. Zubkov, Kh. S. Shikhaliev, N. A. Aksenov, E. R. Kofanov, V. A. Burilov, Yu. I. Baukov, V. F. Traven, E. A. Krasnokutskaya, O. V. Fedotova, A. S. Fisyuk, E. L. Gavrilova, V. A. Mamedov, A. R. Kurbangali eva, I. A. Balova, M. Yu. Krasavin, L. L. Rodina, N. V. Zyk, T. A. Shmigoí, L. G. Voskresenskii, A. S. Semeikin, D. B. Berezin, P. A. Stuzhin, V. D. Filimonov, A. V. Nyuchev, G. P. Sagitullina, A. K. Breí, S. V. Lisina, S. M. Medvedeva, Russ. J. Org. Chem., 2018, 54, 157.
I. Lapin, CNS Drug Reviews, 2006, 7, 471.
G. Comte, J.-B. Daskiewicz, C. Bayet, G. Conseil, A. Viornery-Vanier, C. Dumontet, A. Di Pietro, D. Barron, J. Med. Chem., 2001, 44, 763.
H. Mohrle, C. Miller, Arch. Pharm. (Weinheim), 1983, 316, 160.
P. Christjanson, A. Köösel, K. Siimer, A. Suurpere, J. Eng. Sci., 1997, 37, 928.
German Pat. D 134979.
A. Einhorn, T. Mauermayer, C. Ladisch, G. Schupp, Annalen, 1905, 207.
H. Zaugg, W. Martin, -Amidoalkylations at Carbon, John Wiley & Sons, New York, 1965, 167.pp.
J. Barry, E. Mayeda, S. Ross, Tetrahedron, 1976, 33, 369.
R. Mudududdla, J. Bharate, S. Bharate, J. Org. Chem., 2012, 77.(19), 8821.
A. A. Lagunin, R. K. Goel, D. Y. Gawande, P. Pahwa, T. A. Gloriozova, A. V. Dmitriev, S. M. Ivanov, A. V. Rudik, V. I. Konova, P. V. Pogodin, D. S. Druzhilovsky, V. V. Poroikov, Nat. Prod. Rep., 2014, 31, 1585.
D. A. Borozdenko, S. V. Vorobév, N. M. Kiseleva, Ross. Immunolog. Zh. [Russ. J. Immunolog.], 2016, 10.(19), No. 2(1), 490 (in Russian).
A. G. Shipov, N. A. Orlova, Yu. I. Baukuv, J. Gen. Chem. USSR, 1984, 54, 2640.
P. G. M. Wuts, T. W. Green, Greenes Protective Groups in Organic Aynthesis, 4th ed., John Wiley & Sons, Inc., Hoboken, New Jersey, 2007, 406.pp.
G. M. Sheldrick, Acta Cryst., 2008, A64, 112.
G. M. Sheldrick, Acta Cryst., 2015, A71, 3.
O. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.
A. Sadym, A. Lagunin, D. Filimonov, V. Poroikov, SAR QSAR Environ. Res., 2003, 14, 339.
D. A. Filimonov, A. A. Lagunin, T. A. Gloriozova, A. V. Rudik, D. S. Druzhilovski, P. V. Pogodin, V. V. Poroikov, Chem. Heterocycl. Compd., 2014, 50.3), 444.
A. Lagunin, A. Zakharov, D. Filimonov, V. Poroikov, Mol. Inf., 2011, 30.2–3), 241.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1518–1529, August, 2018.
Rights and permissions
About this article
Cite this article
Negrebetsky, V.V., Vorobyev, S.V., Kramarova, E.P. et al. Lactamomethyl derivatives of diphenols: synthesis, structure, and potential biological activity. Russ Chem Bull 67, 1518–1529 (2018). https://doi.org/10.1007/s11172-018-2250-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2250-0