Abstract:
To enhance the lipophilicity of d-3,5,6-trideoxyinositol monophosphate, the IMPase inhibitor, its bridgehead analogues were suggested on the basis of molecular modeling. Adamantane-1,2- and 1,4-diols were converted into their 1-phosphates via the step of benzylic protection of the secondary hydroxy groups; the Baeyer–Villiger oxidation of 1-hydroxyadamantan-2-one occurred to initially cleave C(1)–C(2) bond.
Citation:
O. N. Zefirova, I. S. Raguzin, V. V. Gogol, E. V. Nurieva, M. S. Belenikin, “Phosphates of bridgehead alcohols as putative inositol monophosphatase inhibitors: molecular design and synthetic approach”, Mendeleev Commun., 21:5 (2011), 242–244
Linking options:
https://www.mathnet.ru/eng/mendc2930
https://www.mathnet.ru/eng/mendc/v21/i5/p242
This publication is cited in the following 7 articles:
Chengyuan Shao, Yani Zhao, Senkai Han, Fu Huang, Hua Jiang, Ying Wang, “Molecular Differentiation and Fingerprinting Based on the Conformational Diversity of Cage”, SSRN Journal, 2021
Valery M. Dembitsky, Tatyana A. Gloriozova, Vladimir V. Poroikov, “Pharmacological profile of natural and synthetic compounds with rigid adamantane-based scaffolds as potential agents for the treatment of neurodegenerative diseases”, Biochemical and Biophysical Research Communications, 529:4 (2020), 1225
N. A. Zefirov, E. V. Nurieva, Yu. A. Pikulina, A. V. Ogon´kov, B. Wobith, S. A. Kuznetsov, O. N. Zefirova, “Adamantane acid esters with alkoxyaryl alcohols: Synthesis, antiproliferative activity, and influence on microtubule network of tumor cells”, Russ Chem Bull, 66:8 (2017), 1503
D. V. Shishov, E. V. Nurieva, N. S. Zefirov, A. V. Mamaeva, O. N. Zefirova, “Synthesis of 5-hydroxy-4-methoxytricyclo[7.3.1.02,7]trideca-2,4,6-trien- 8-one – precursor of putative bioisosteric colchicine analogues”, Mendeleev Commun., 24:6 (2014), 370–371
O. N. Zefirova, N. S. Zefirov, “Targeted application of bridged fragments in the design of physiologically active compounds”, Russ Chem Bull, 62:2 (2013), 325
O. N. Zefirova, E. D. Plotnikova, E. V. Nurieva, D. I. Peregud, M. V. Onufriev, N. V. Gulyaeva, “Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity”, Mendeleev Commun., 23:2 (2013), 76–77
I. S. Raguzin, V. V. Gogol, E. V. Nurieva, V. N. Nuriev, O. N. Zefirova, “Synthesis and study of the inhibitory activity of adamantylphosphates with respect to Myo-inositolmonophosphatase”, Moscow Univ. Chem. Bull., 67:1 (2012), 30
Contact us: