Login Register Cart 0
Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis of Polyalkoxymethylenedioxy-1,4-naphthoquinones from Parsley Seed Metabolite

Author(s): Alexander E. Varakutin, Egor A. Muravsky, Victor N. Khrustalev, Alexander V. Samet and Victor V. Semenov*

Volume 28, Issue 1, 2024

Published on: 27 December, 2023

Page: [40 - 45] Pages: 6

DOI: 10.2174/0113852728283175231218092342

Price: $65

Abstract

A convenient synthesis of polyalkoxy-1,4-naphthoquinones, good starting materials for analogues of natural quinones, has been developed. Bromonaphthoquinone, more stable than its hydroxylated analogue, turned out to be a convenient and accessible key synthon for the preparation of various polyalkoxylated naphthoquinones. The obtained quinones could be useful starting materials for the preparation of biologically active polymethoxy- and hydroxy-methylenedioxynaphthoquinones.

« Previous Next »
Graphical Abstract

[1]
Thomson, R.H. Naturally occurring quinones IV: Recent advances; Blackie Academic & Professional, 1997.
[2]
Hou, Y.; Vasileva, E.A.; Carne, A.; McConnell, M. Naphthoquinones of the spinochrome class: Occurrence, isolation, biosynthesis and biomedical applications. RSC Advances, 2018, 8, 32637-32650.
[http://dx.doi.org/10.1039/C8RA04777D] [PMID: 35547692]
[3]
Chai, C.L.L.; Elix, J.A.; Moore, F.K.E. Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins. J. Org. Chem., 2006, 71(3), 992-1001.
[http://dx.doi.org/10.1021/jo0519561] [PMID: 16438511]
[4]
Masuda, K.; Funayama, S.; Komiyama, K.; Unezawa, I.; Ito, K. Constituents of Tritonia crocosmaeflora, I. Tricrozarin A, a novel antimicrobial naphthazarin derivative. J. Nat. Prod., 1987, 50(3), 418-421.
[http://dx.doi.org/10.1021/np50051a012] [PMID: 3668558]
[5]
Daironas, J.; Zilfikarov, I. Natural 1,4-naphthoquinones: Prospects for medical use; Schyolkovo, 2011.
[6]
Hanumaiah, T.; Rao, G.S.R.; Rao, C.P.; Rao, K.V.J.; Cowe, H.J.; Cox, P.J.; Howie, R.A.; Marshall, D.S.; Thompson, R.H. Isofuranonaphthoquinones from ventilago maderaspatana. Tetrahedron, 1985, 41(3), 635-642.
[http://dx.doi.org/10.1016/S0040-4020(01)96511-1]
[7]
Rizzacasa, M.A.; Sargent, M.V. The structure and synthesis of nepenthone-A, a naphthoquinone from Nepenthes rafflesiana. J. Chem. Soc., Perkin Trans. 1, 1987, 2017-2022.
[http://dx.doi.org/10.1039/p19870002017]
[8]
Bringmann, G.; Rüdenauer, S.; Irmer, A.; Bruhn, T.; Brun, R.; Heimberger, T.; Stühmer, T.; Bargou, R.; Chatterjee, M. Antitumoral and antileishmanial dioncoquinones and ancistroquinones from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and Ancistrocladus abbreviatus (Ancistrocladaceae). Phytochemistry, 2008, 69(13), 2501-2509.
[http://dx.doi.org/10.1016/j.phytochem.2008.06.019] [PMID: 18723197]
[9]
Samet, A.V.; Shevchenko, O.G.; Rusak, V.V.; Chartov, E.M.; Myshlyavtsev, A.B.; Rusanov, D.A.; Semenova, M.N.; Semenov, V.V. Antioxidant activity of natural allylpolyalkoxybenzene plant essential oil constituents. J. Nat. Prod., 2019, 82(6), 1451-1458.
[http://dx.doi.org/10.1021/acs.jnatprod.8b00878] [PMID: 31244145]
[10]
Semenov, V.V.; Rusak, V.V.; Chartov, E.M.; Zaretskii, M.I.; Konyushkin, L.D.; Firgang, S.I.; Chizhov, A.O.; Elkin, V.V.; Latin, N.N.; Bonashek, V.M.; Stas’eva, O.N. Polyalkoxybenzenes from plant raw materials 1. Isolation of polyalkoxybenzenes from CO2 extracts of Umbelliferae plant seeds. Russ. Chem. Bull., 2007, 56(12), 2448-2455.
[http://dx.doi.org/10.1007/s11172-007-0389-1]
[11]
Semenov, V.V.; Kiselyov, A.S.; Titov, I.Y.; Sagamanova, I.K.; Ikizalp, N.N.; Chernysheva, N.B.; Tsyganov, D.V.; Konyushkin, L.D.; Firgang, S.I.; Semenov, R.V.; Karmanova, I.B.; Raihstat, M.M.; Semenova, M.N. Synthesis of antimitotic polyalkoxyphenyl derivatives of combretastatin using plant allylpolyalkoxybenzenes. J. Nat. Prod., 2010, 73(11), 1796-1802.
[http://dx.doi.org/10.1021/np1004278] [PMID: 21049975]
[12]
Tsyganov, D.V.; Demchuk, D.V.; Adaeva, O.I.; Konyushkin, L.D.; Minyaev, M.E.; Khrustalev, V.N.; Semenov, V.V. Synthesis and X-ray diffraction analysis of coenzyme Q derivatives obtained from natural polyalkoxyallylbenzenes. Mendeleev Commun., 2023, 33(4), 539-542.
[http://dx.doi.org/10.1016/j.mencom.2023.06.032]
[13]
Adaeva, O.I.; Demchuk, D.V.; Semenov, V.V. 6,7-dihydroxy-5,8-dimethoxy-2H-chromen-2-one. Molbank, 2023, 2023(3), M1702.
[http://dx.doi.org/10.3390/M1702]
[14]
Varakutin, A.E.; Shinkarev, I.Y.; Muravsky, E.A.; Nasyrova, D.I.; Samigullina, A.I.; Semenova, M.N.; Semenov, V.V. Synthesis of tetraalkoxyaryldihydrobenzo[g]indazoles from metabolites of dill and parsley seeds essential oil. Tetrahedron, 2023, 137, 133365.
[http://dx.doi.org/10.1016/j.tet.2023.133365]
[15]
Varakutin, A.E.; Muravsky, E.A.; Tsyganov, D.V.; Shinkarev, I.Y.; Samigullina, A.I.; Kuptsova, T.S.; Chuprov-Netochin, R.N.; Smirnova, A.V.; Khomutov, A.A.; Leonov, S.V.; Semenova, M.N.; Semenov, V.V. Synthesis of chalcones with methylenedioxypolymethoxy fragments based on plant metabolites and study of their antiproliferative properties. Russ. Chem. Bull., 2023, 72(7), 1632-1647.
[http://dx.doi.org/10.1007/s11172-023-3943-6]
[16]
Nishibori, K. Isolation of Echinochrome A from the Spines of the Sea Urchin, Diadema setosum (Leske). Nature, 1959, 184(4694), 1234-1234.
[http://dx.doi.org/10.1038/1841234a0]
[17]
Nishibori, K. Isolation of echinochrome A from the spines of the sea urchin, Stomopneustes variolaris (Lamarck). Nature, 1961, 192(4809), 1293-1294.
[http://dx.doi.org/10.1038/1921293a0] [PMID: 14479945]
[18]
Mishchenko, N.P.; Fedoreev, S.A.; Bagirova, V.L. Histochrome: A new original domestic drug. Pharm. Chem. J., 2003, 37(1), 48-52.
[http://dx.doi.org/10.1023/A:1023659331010]
[19]
Baillie, A.C.; Thomson, R.H. Quinones. Part VII. New routes to 2-hydroxy-1,4-naphthaquinones. J. Chem. Soci. C :Org., 1966, 2184-2186.
[http://dx.doi.org/10.1039/j39660002184]
[20]
Ameer, F.; Giles, R.G.F.; Green, I.R.; Pearce, R. Synthesis of methoxy‐2‐hydroxy‐1,4‐naphthoquinones and reaction of one isomer with aldehydes under basic conditions. Synth. Commun., 2004, 34(7), 1247-1258.
[http://dx.doi.org/10.1081/SCC-120030312]
[21]
Ogata, T.; Yoshida, T.; Shimizu, M.; Tanaka, M.; Fukuhara, C.; Ishii, J.; Nishiuchi, A.; Inamoto, K.; Kimachi, T. Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C. Tetrahedron, 2016, 72(11), 1423-1432.
[http://dx.doi.org/10.1016/j.tet.2016.01.040]
[22]
Bekaert, A.; Provot, O.; Rasolojaona, O.; Alami, M.; Brion, J.D. N-Methylpyrrolidin-2-one hydrotribromide (MPHT) a mild reagent for selective bromination of carbonyl compounds: Synthesis of substituted 2-bromo-1-naphtols. Tetrahedron Lett., 2005, 46(24), 4187-4191.
[http://dx.doi.org/10.1016/j.tetlet.2005.04.049]
[23]
Evans, P. Scaling and assessment of data quality. Acta Crystallogr. D Biol. Crystallogr., 2006, 62(1), 72-82.
[http://dx.doi.org/10.1107/S0907444905036693] [PMID: 16369096]
[24]
Battye, T.G.G.; Kontogiannis, L.; Johnson, O.; Powell, H.R.; Leslie, A.G.W. iMOSFLM: A new graphical interface for diffraction-image processing with MOSFLM. Acta Crystallogr. D Biol. Crystallogr., 2011, 67(4), 271-281.
[http://dx.doi.org/10.1107/S0907444910048675] [PMID: 21460445]
[25]
Winn, M.D.; Ballard, C.C.; Cowtan, K.D.; Dodson, E.J.; Emsley, P.; Evans, P.R.; Keegan, R.M.; Krissinel, E.B.; Leslie, A.G.W.; McCoy, A.; McNicholas, S.J.; Murshudov, G.N.; Pannu, N.S.; Potterton, E.A.; Powell, H.R. Overview of the CCP4 suite and current developments. Acta Crystallogr. D Biol. Crystallogr., 2011, 67, 235-242.
[http://dx.doi.org/10.1107/S0907444910045749] [PMID: 21460441]
[26]
Sheldrick, G.M. SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr. A Found. Adv., 2015, 71(1), 3-8.
[http://dx.doi.org/10.1107/S2053273314026370] [PMID: 25537383]
[27]
Sheldrick, G.M. Crystal structure refinement with SHELXL. Acta Crystallogr. C Struct. Chem., 2015, 71(1), 3-8.
[http://dx.doi.org/10.1107/S2053229614024218] [PMID: 25567568]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy