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Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems

Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
Aleksandr Mikhailovich Churakov
Oleg Alekseevich Luk'yanov 1
Oleg Alekseevich Luk'yanov
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
Alexey Yu Sukhorukov 1
Alexey Yu Sukhorukov
Vladimir Alexandrovich Tartakovsky
Published 2015-11-09
Focus articleVolume 25, Issue 6, 399-409
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Zlotin S. G. et al. Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 399-409.
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Zlotin S. G., Churakov A. M., Luk'yanov O. A., Makhova N. N., Sukhorukov A. Yu., Tartakovsky V. A. Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 399-409.
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TY - JOUR
DO - 10.1016/j.mencom.2015.11.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.001
TI - Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems
T2 - Mendeleev Communications
AU - Zlotin, Sergei Grigorievich
AU - Churakov, Aleksandr Mikhailovich
AU - Luk'yanov, Oleg Alekseevich
AU - Makhova, Nina Nikolaevna
AU - Sukhorukov, Alexey Yu
AU - Tartakovsky, Vladimir Alexandrovich
PY - 2015
DA - 2015/11/09
PB - Mendeleev Communications
SP - 399-409
IS - 6
VL - 25
ER -
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@article{2015_Zlotin,
author = {Sergei Grigorievich Zlotin and Aleksandr Mikhailovich Churakov and Oleg Alekseevich Luk'yanov and Nina Nikolaevna Makhova and Alexey Yu Sukhorukov and Vladimir Alexandrovich Tartakovsky},
title = {Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.001},
number = {6},
pages = {399--409},
doi = {10.1016/j.mencom.2015.11.001}
}
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Zlotin, Sergei Grigorievich, et al. “Novel approaches to pharmacology-oriented and energy rich organic nitrogen–oxygen systems.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 399-409. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.001.
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Abstract

Organic compounds bearing semi-polar nitrogen–oxygen bonds are considered as perspective platform for designing socially important medications and high energy materials. Herein, recently developed original syntheses of monocyclic and fused 1,2,3,4-tetrazine 1,3-dioxides, various (methylene)bis(1-oxy-1-triazene 2-oxide) derivatives, furoxan-containing polyheterocyclic scaffolds and diastereoor enantiomerically enriched functionalized aliphatic nitro compounds are summarized. Prospects for their practical applications are outlined.

References

1.
10.1016/j.mencom.2015.11.001_bib0005
Agrawal
Organic Chemistry of Explosives, 2007
2.
(a) F. Furchgott, Angew. Chem. Int. Ed., 1999, 38, 1870; (b) F. Murad, Angew. Chem. Int. Ed., 1999, 38, 1856; (c) L. J. Ignarro, Angew. Chem. Int. Ed., 1999, 38, 1882.
3.
(a) M. Willmot, L. Gray, C. Gibson, S. Murphy and P. M. Bath, Nitric Oxide, 2005, 12, 141; (b) Nitric Oxide Donors: For Pharmaceutical and Biological Applications, eds. P. G. Wang, T.B. Cai and N. Taniguchi, Wiley-VCH, Weinheim, 2005; (c) R. Scatena, P. Bottoni, A. Pontoglio and B. Giardina, Curr. Med. Chem., 2010, 17, 61; (d) P. Krause, E. Waetzig, H. Acil, S. Koenig, K. Unthan-Fechner, D. Tsikas and I. Probst, Nitric Oxide, 2010, 23, 220; (e) R. A. M. Serafim, M.C. Primi, G.H. G. Trossini and E. I. Ferreira, Curr. Med. Chem., 2012, 19, 386.
4.
(a) Goodman and Gilman's the Pharmacological Basis of Therapeutics, eds. J. G. Hardman, L.E. Limbird and A. G. Gilman, McGraw-Hill, New York, 2001; (b) Basic Neurochemistry: Molecular, Cellular and Medical Aspects, eds. G. J. Siegel, R.W. Albers, S. Brady and D. Price, Academic Press, Elsevier, Boston, 2006.
5.
Asymmetric organocatalysis in total synthesis – a trial by fire
Marqués-López E., Herrera R.P., Christmann M.
Natural Product Reports, 2010
6.
Progress in 1,2,3,4-Tetrazine Chemistry
Churakov A.M., Tartakovsky V.A.
Chemical Reviews, 2004
7.
(a) Q. Wu, Y. Pan, X. Xia, Y. Shao, W. Zhu and H. Xiao, Struct. Chem., 2013, 24, 1579; (b) F. Xiang, Q. Wu, W. Zhu and H. Xiao, Can. J. Chem., 2013, 91, 1233; (c) Q. Wu, W. Zhu and H. Xiao, J. Chem. Eng. Data, 2013, 58, 2748.
8.
Theoretical Investigation of Several 1,2,3,4-Tetrazine-Based High-Energy Compounds
Tan B., Huang M., Huang H., Long X., Li J., Nie F., Huang J.
Propellants, Explosives, Pyrotechnics, 2013
9.
Are DTTO and iso -DTTO Worthwhile Targets for Synthesis?
Christe K.O., Dixon D.A., Vasiliu M., Wagner R.I., Haiges R., Boatz J.A., Ammon T.L.
Propellants, Explosives, Pyrotechnics, 2015
10.
(a) M. S. Klenov, O.V. Anikin, A.M. Churakov, Yu. A. Strelenko, I.V. Fedyanin, I.V. Ananyev and V. A. Tartakovsky, Eur. J. Org. Chem., 2015, 6170; (b) A. Yu. Tyurin, A.M. Churakov, Yu. A. Strelenko, M.O. Ratnikov and V. A. Tartakovsky, Russ. Chem. Bull., Int. Ed., 2006, 55, 1648 (Izv. Akad. Nauk, Ser. Khim., 2006, 1589); (c) M. S. Klenov, A.M. Churakov, Yu. A. Strelenko, I.V. Ananyev, K.A. Lyssenko and V. A. Tartakovsky, Tetrahedron Lett., 2015, 56, 5437.
11.
Derivatives of Benzotetrazine-1,3-dioxide Are New NO-donors, Activators of Soluble Guanylate Cyclase, and Inhibitors of Platelet Aggregation
Pyatakova N.V., Khropov Y.V., Churakov A.M., Tarasova N.I., Serezhenkov V.A., Vanin A.F., Tartakovsky V.A., Severina I.S.
Biochemistry (Moscow), 2002
12.
A. M. Churakov, S.L. Ioffe, V.A. Tartakovskii, O.G. Busygina, Yu. V. Khropov and I. S. Severina, RF Patent 2123526, 1998 (Chem. Abstr., 2000, 133, 55324).
13.
N. V. Pyatakova, A.M. Kozlov, A.M. Churakov, O. Yu. Smirnov, Yu. V. Khropov, N.S. Saprykina, N.G. Bogdanova, S.L. Ioffe, I.S. Severina and V. A. Tartakovsky, RF Patent 2192857, 2002 (Chem. Abstr., 2003, 138, 314555).
14.
N. V. Dolgova, A.M. Churakov, O. Yu. Smirnov, Yu. V. Khropov, N.G. Bogdanova, N.V. Mast, S.L. Ioffe, O.D. Lopina and V. A. Tartakovsky, RF Patent 2186108, 2002 (Chem. Abstr., 2003, 138, 133153).
15.
Synthesis of 1,2,3,4-tetrazine 1,3-dioxides annulated with 1,2,3-triazoles and 1,2,3-triazole 1-oxides
Voronin A.A., Zelenov V.P., Churakov A.M., Strelenko Y.A., Fedyanin I.V., Tartakovsky V.A.
Tetrahedron, 2014
16.
Synthesis of 1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 4,6-dioxide and its methyl derivatives
Voronin A.A., Zelenov V.P., Churakov A.M., Strelenko Y.A., Tartakovsky V.A.
Russian Chemical Bulletin, 2015
17.
(a) V. G. Granik and N. B. Grigoriev, Oksid azota (NO). Novyi put’ k poisku lekarstv (Nitric oxide (NO). New Route to Drug Design), Vuzovskaya Kniga, Moscow, 2004 (in Russian); (b) J. A. Hrabie and L. K. Keefer, Chem. Rev., 2002, 102, 1135.
18.
(a) D. Biswas, R.J. Holland, J.R. Deschamps, Z. Cao, L.K. Keefer and J. E. Saavedra, J. Org. Chem., 2012, 77, 10804; (b) R. S. Drago and B. R. Karstetter, J. Am. Chem. Soc., 1961, 83, 1819; (c) D. Biswas, J.A. Hrabie, J.E. Saavedra, Z. Cao, L.K. Keeffer, J. Jvanic and R. J. Holland, J. Org. Chem., 2014, 79, 4612.
19.
(a) R. J. Holland, J.R. Klose, J.R. Deschampe, Z. Cao, L.K. Keefer and J. E. Saavedra, J. Org. Chem., 2014, 79, 9389; (b) R. S. Nandurdikar, A. E. Maciag, Z. Cao, L.K. Keefer and J. E. Saavedra, Bioorg. Med. Chem., 2012, 20, 2026.
20.
Synthesis of methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides) and their analogs
Smirnov G.A., Gordeev P.B., Nikitin S.V., Pokhvisneva G.V., Ternikova T.V., Luk´yanov O.A.
Russian Chemical Bulletin, 2015
22.
10.1016/j.mencom.2015.11.001_bib0110
Korolev
Acta Naturale, 2013
23.
(a) L. I. Khmel’nitskii, S.S. Novikov and T. I. Godovikova, Khimiya furoksanov. Stroenie i sintez (Chemistry of Furoxans. Structure and Synthesis), 2nd edn., Nauka, Moscow, 1996 (in Russian); (b) L. I. Khmel’nitskii, S.S. Novikov and T. I. Godovikova, Khimiya furoksanov. Reaktsii i primenenie (Chemistry of Furoxans. Reactions and Application), 2nd edn., Nauka, Moscow, 1996.(in Russian).
24.
Ananikov V.P., Khokhlova E.A., Egorov M.P., Sakharov A.M., Zlotin S.G., Kucherov A.V., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2015
26.
Searching for new NO-donor aspirin-like molecules: Furoxanylacyl derivatives of salicylic acid and related furazans
Lazzarato L., Cena C., Rolando B., Marini E., Lolli M.L., Guglielmo S., Guaita E., Morini G., Coruzzi G., Fruttero R., Gasco A.
Bioorganic and Medicinal Chemistry, 2011
27.
(a) A. I. Stepanov, D.V. Dashko and A. A. Astrat’ev, Central Eur. J. Energ. Mater., 2012, 9, 329; (b) V. I. Pepekin, B.L. Korsunskii and Yu. N. Matyushin, Comb. Expl. Shock Waves, 2008, 44, 110 (Fiz. Goreniya Vzryva, 2008, 44, 123); (c) A. O. Chizhov, N.N. Makhova, I.V. Kuchurov, A.B. Sheremetev and S. G. Zlotin, Mendeleev Commun., 2014, 24, 165; (d) D. Fischer, T.M. Klapötke and J. Stierstorfer, Eur. J. Inorg. Chem., 2014, 5808.
28.
(a) N. N. Makhova, A.S. Kulikov, S.I. Molotov and E. L. Baryshnikova, Pure Appl. Chem., 2004, 76, 1691; (b) I. V. Ovchinnikov, A.O. Finogenov, M.A. Epishina, A.S. Kulikov, Yu. A. Strelenko and N. N. Makhova, Russ. Chem. Bull., Int. Ed., 2009, 58, 2137 (Izv. Akad. Nauk, Ser. Khim., 2009, 2072); (c) N. N. Makhova and A. C. Kulikov, Russ. Chem. Rev., 2013, 82, 1007; (d) L. L. Fershtat, I.V. Ovchinnikov and N. N. Makhova, Tetrahedron Lett., 2014, 55, 2398; (e) L. L. Fershtat, M.I. Struchkova, A.S. Goloveshkin, I.S. Bushmarinov and N. N. Makhova, Heteroat. Chem., 2014, 25, 226.
29.
Vasorelaxant and antiplatelet activity of 4,7-dimethyl-1,2,5-oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide: Role of soluble guanylate cyclase, nitric oxide and thiols
Kots A.Y., Grafov M.A., Khropov Y.V., Betin V.L., Belushkina N.N., Busygina O.G., Yazykova M.Y., Ovchinnikov I.V., Kulikov A.S., Makhova N.N., Medvedeva N.A., Bulargina T.V., Severina I.S.
British Journal of Pharmacology, 2000
31.
Fershtat L.L., Ashirbaev S.S., Kulikov A.S., Kachala V.V., Makhova N.N.
Mendeleev Communications, 2015
32.
An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy
Fershtat L.L., Epishina M.A., Kulikov A.S., Ovchinnikov I.V., Ananyev I.V., Makhova N.N.
Tetrahedron, 2015
34.
An effective synthesis of (1H-1,2,4-triazol-3-yl)furoxans
Fershtat L.L., Epishina M.A., Ovchinnikov I.V., Kachala V.V., Makhova N.N.
Chemistry of Heterocyclic Compounds, 2015
35.
Konstantinova L.S., Amelichev S.A., Zlotin S.G., Struchkova M.I., Godovikova T.I., Rakitin O.A.
Mendeleev Communications, 2015
36.
3-R-4-Nitro-6,7-furoxanobenzo[d]isoxazoles – a new type of condensed nitroarenes capable of Diels–Alder reaction
Bastrakov M.A., Starosotnikov A.M., Kachala V.V., Dalinger I.L., Shevelev S.A.
Chemistry of Heterocyclic Compounds, 2015
37.
Effects of N-Nitropyrazoles on Ocular Blood Flow of Rabbits and Retinal Function Recovery of Rat Eyes after Ischemic Insults
Xuan B., Wang T., Chiou G.C., Dalinger I., Shkineva T.K., Shevelev S.A.
Journal of Ocular Pharmacology and Therapeutics, 2002
38.
Kuchurov I.V., Fomenkov I.V., Zlotin S.G., Tartakovsky V.A.
Mendeleev Communications, 2012
39.
(a) S. S. Novikov, G.A. Shvekhgeimer, V.V. Sevostyanova and V. A. Shlyapochnikov, Khimiya alifaticheskikh i tsikloalifaticheskikh nitrosoedinenii (Chemistry of Aliphatic and Cycloaliphatic Nitro Compounds), Khimiya, Moscow, 1974 (in Russian); (b) E. E. Gilbert and G. P. Sollott, J. Org. Chem., 1980, 45, 5405; (c) T. G. Archibald, K. Baum, M.C. Cohen and L. C. Garver, J. Org. Chem., 1989, 54, 2869; (d) R. P. Kashyap, A.P. Marchand, R. Sharma, W.H. Watson and U. R. Zope, J. Org. Chem., 1993, 58, 759; (e) P. E. Eaton, R. Gilardi, J. Hain, N. Kanomata, J. Li, K.A. Lukin and E. Punzalan, J. Am. Chem. Soc., 1997, 119, 9591.
40.
(a) L. S. Aitken, N.R. Arezki, A. Dell’Isola and A. J. A. Cobb, Synthesis, 2013, 45, 2627; (b) S. Z. Zard, Helv. Chim. Acta, 2012, 95, 1730; (c) R. Ballini and M. Petrini, ARKIVOC, 2009, 9, 195; (d) R. Ballini and M. Petrini, Tetrahedron, 2004, 60, 1017.
41.
10.1016/j.mencom.2015.11.001_bib0205
Ono
The Nitro Group in Organic Chemistry, 2001
42.
Conjugate Addition of Nitroalkanes to an Acrylate Equivalent. Stereocontrol at C-α of the Nitro Group through Double Catalytic Activation
43.
(a) Y.-P. Li, Z.-J. Li and X.-B. Meng, Carbohydr. Res., 2011, 346, 1801; (b) R. G. Soengas and A. M. Estévez, Eur. J. Org. Chem., 2010, 5190; (c) L. Kh. Faizullina, M.G. Safarov, L.V. Spirikhin, V.S. Kolosnitsyn, Yu. A. Kondrova and F. A. Valeev, Russ. J. Org. Chem., 2011, 47, 914.(Zh. Org. Khim., 2011, 47, 897).
45.
Tandem [4+2]/[3+2] Cycloadditions of Nitroalkenes
Denmark S.E., Thorarensen A.
Chemical Reviews, 1996
46.
(a) C.-Y. Zhu, X.-M. Deng, X.-L. Sun, J.-C. Zhenga and Y. Tang, Chem. Commun., 2008, 738; (b) T. Kano, A. Yamamoto, S. Song and K. Maruoka, Chem. Commun., 2011, 4358; (c) C. D. Schmidt, J. Kaschel, T.F. Schneider, D. Kratzert, D. Stalke and D. B. Werz, Org. Lett., 2013, 15, 6098.
47.
Catalytic asymmetric Henry reactions of silyl nitronates with aldehydes
Risgaard T., Gothelf K.V., Jørgensen K.A.
Organic and Biomolecular Chemistry, 2003
50.
Novel Formal [3+3] Cycloaddition of Silyl Nitronates with Activated Cyclo­propanes and Its Application in the Synthesis of Pyrroline-N-oxides
Ioffe S., Mikhaylov A., Novikov R., Khomutova Y., Arkhipov D., Korlyukov A., Tabolin A., Tomilov Y.
Synlett, 2014
51.
Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis
Wilson J.E., Casarez A.D., MacMillan D.W.
Journal of the American Chemical Society, 2009
52.
A General Metal-Assisted Synthesis of α-Halo Oxime Ethers from Nitronates and Nitro Compounds
Sukhorukov A.Y., Kapatsyna M.A., Yi T.L., Park H.R., Naumovich Y.A., Zhmurov P.A., Khomutova Y.A., Ioffe S.L., Tartakovsky V.A.
European Journal of Organic Chemistry, 2014
54.
Nitroalkenes in the synthesis of carbocyclic compounds
Halimehjani A.Z., Namboothiri I.N., Hooshmand S.E.
RSC Advances, 2014
55.
(a) Science of Synthesis: Asymmetric Organocatalysis, eds. B. List and K. Maruoka, Thieme, Stuttgart, 2012, vols. 1, 2; (b) Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, ed. P. I. Dalco, Wiley-VCH, Weinheim, 2013, vols. 1-3.
56.
Comparative pharmacological activity of optical isomers of phenibut
Dambrova M., Zvejniece L., Liepinsh E., Cirule H., Zharkova O., Veinberg G., Kalvinsh I.
European Journal of Pharmacology, 2008
59.
Water-Compatible Iminium Activation: Organocatalytic Michael Reactions of Carbon-Centered Nucleophiles with Enals
Palomo C., Landa A., Mielgo A., Oiarbide M., Puente Á., Vera S.
Angewandte Chemie - International Edition, 2007
62.
Preparation of (−)-Nutlin-3 Using Enantioselective Organocatalysis at Decagram Scale
Davis T.A., Vilgelm A.E., Richmond A., Johnston J.N.
Journal of Organic Chemistry, 2013
68.
Asymmetric total synthesis of (−)-venlafaxine using an organocatalyst
69.
Catalytic Enantioselective Henry Reactions of Isatins: Application in the Concise Synthesis of ( S )‐(−)‐Spirobrassinin
Liu L., Zhang S., Xue F., Lou G., Zhang H., Ma S., Duan W., Wang W.
Chemistry - A European Journal, 2011
70.
Applications of asymmetric organocatalysis in medicinal chemistry
Alemán J., Cabrera S.
Chemical Society Reviews, 2013
71.
10.1016/j.mencom.2015.11.001_bib0355
Kristensen
2013
72.
Ionic Liquid Organocatalysts
Siyutkin D.E., Kucherenko A.S., Zlotin S.G.
2013
76.
Primary Amine Attached to anN-(Carboxyalkyl)imidazolium Cation: A Recyclable Organocatalyst for the Asymmetric Michael Reaction
Kucherenko A.S., Lisnyak V.G., Chizhov A.O., Zlotin S.G.
European Journal of Organic Chemistry, 2014
77.
Pursuing practical elegance in chemical synthesis