Mіnі-rеvіеw: Advаnсеs іn thе sуnthеsіs аnd bіоlоgісаl асtіvіtу оf bеnzоfurохаn аnd furохаn dеrіvаtіvеs
Keywords:
bеnzоfurохаn, furохаn, NО dоnоr, hеtеrосусlіс соmроunds, hуbrіd соmроunds, аntіbасtеrіаl рrореrtіеs, аntіvіrаl аnd аntіtumоr drugs
Abstract
Benzofuroxan and furoxan derivatives are heterocyclic compounds well known for their ability to act as nitric oxide (NO) donors. Due to their NO-releasing properties, these compounds have attracted considerable attention for their antimicrobial, antiviral, and antitumor activities. Their potential use in treating cardiovascular, gastrointestinal, and neurodegenerative disorders further underscores their pharmacological relevance. Given the increasing research interest in these compounds, there is a need to consolidate recent findings related to their chemical properties and biological potential. This mini-review aims to provide an up-to-date overview of the synthetic strategies and bioactivities of benzofuroxan and furoxan derivatives. Rather than focusing on ring synthesis, this review highlights the reactivity of side-chain functional groups and the design of hybrid molecules. Representative examples of drug-like compounds are discussed, along with their biological profiles. The review also explores emerging directions in the development of novel NO donors based on these frameworks with improved pharmaceutical efficacy and controlled NO release.
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3 N.B.Grigoriev VGG (2004) Oxid Azota (NO): Novyi put’ k Poisku Lekarstv [Nitric Oxide (NO): New Approach to Drug Search]. University Book, Moscow.
4 Fershtat LL, Makhova NN (2017) ChemMedChem 12:622–638. https://doi.org/10.1002/cmdc.201700113
5 Gasco A, Fruttero R, Sorba G, Di Stilo A, Calvino R (2004) Pure Appl Chem 76:973–981. https://doi.org/10.1351/pac200476050973
6 Cerecetto H, González M (2007) Benzofuroxan and Furoxan. Chemistry and Biology. pp 265–308. https://doi.org/10.1007/7081_2007_064
7 Medana C, Di Stilo A, Visentin S, Fruttero R, Gasco A, Ghigo D, et al. (1999) Pharm Res 16:956–60. http://dx.doi.org/10.1023/a:1018974409622
8 Abu Yousef M, Matsubara R (2023) RSC Adv 13:5228–5248. http://dx.doi.org/10.1039/D3RA00189J
9 Mallory FB, Cammarata A (1966) J Am Chem Soc 88:61–64. http://dx.doi.org/10.1021/ja00953a012
10 Ferioli R, Folco GC, Ferretti C, Gasco AM, Medana C, Fruttero R, et al. (1995) Br J Pharmacol 114:816–820. http://dx.doi.org/10.1111/j.1476-5381.1995.tb13277.x
11 R.Calvino, V.Mortarini, A.Gasco MAB and MLR (1977) Synth Antimicrob Act 12:157–159.
12 Cerecetto H, Porcal W (2005) Mini-Reviews Med Chem 5:57–71. http://dx.doi.org/10.2174/1389557053402864
13 J.Stevens, M. Schweizer GR (2001)Some recent studies on benzofuraxansJournal of the American Chemical Society 123:
14 Flores-Santana W, Salmon DJ, Donzelli S, Switzer CH, Basudhar D, Ridnour L, et al. (2011) Antioxid Redox Signal 14:1659–1674. http://dx.doi.org/10.1089/ars.2010.3841
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16 Sebban M, Goumont R, Hallé JC, Terrier F, Marrot J (1999) Chem Commun 1009–1010. http://dx.doi.org/10.1039/a902170a
17 Y.Fukai, T.Miyazawa, M.Kojoh, T.Takabatake MH (2001) JHeterocyclChem 38:531–534.
18 David M. Jameson and Shan S. Wong (2011) Chemistry of Protein and Nucleic Acid Cross-Linking and Conjugation.
19 Kumar S, Arora A, Chaudhary R, Kumar R, Len C, Mukherjee M, et al. (2024) Top Curr Chem 382:34. http://dx.doi.org/10.1007/s41061-024-00476-7
20 Bohn H, Brendel J, Martorana PA, Schönafinger K (1995) Br J Pharmacol 114:1605–1612. http://dx.doi.org/10.1111/j.1476-5381.1995.tb14946.x
21 Ustyuzhanina NE, Fershtat LL, Gening ML, Nifantiev NE, Makhova NN (2018) Mendeleev Commun 28:49–51. http://dx.doi.org/10.1016/j.mencom.2018.01.016
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23 Wang PG, Bill Cai T, Taniguchi N (2005) Nitric Oxide Donors. Wiley. http://dx.doi.org/10.1002/3527603751
24 Fershtat LL, Makhova NN (2017) ChemMedChem 12:622–638. http://dx.doi.org/10.1002/cmdc.201700113
25 Burov ON, Kletskii ME, Fedik NS, Lisovin A V, Kurbatov S V (2015) Chem Heterocycl Compd 51:951–960. http://dx.doi.org/10.1007/s10593-016-1804-z
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27 Zhilin ES, Fershtat LL, Bystrov DM, Kulikov AS, Dmitrienko AO, Ananyev I V., et al. (2019) European J Org Chem 2019:4248–4259. http://dx.doi.org/10.1002/ejoc.201900622
28 Zhilin ES, Polkovnichenko MS, Ananyev I V., Fershtat LL, Makhova NN (2020) ChemPhotoChem 4:5346–5354. http://dx.doi.org/10.1002/cptc.202000157
29 Garipov MR, Nikitina EV, Petukhov AS, Shtyrlin YuG, Strelnik AD (2013) Antibacterial compounds based on sulfanilic acid and pyridoxine [Antibakterial’nye soedineniya na osnove sul’fanilovoy kisloty i piridoksina]. Patent of the Russian Federation RF Patent 2480471, Int. Cl. C07D491/052. Published 27.04.2013. (In Russian)
30 Serkov IV, Bezuglov VV (2009) Uspekhi Khimii [Russian Chemical Reviews] 78:442–465. (In Russian)
31 Katritzky AR, Gordeev MF (1993) Heterocycles 35:483–518. http://dx.doi.org/10.3987/REV-92-SR2
32 Ghosh P, Ternai B, Whitehouse M (1981) Med Res Rev 1:159–187. http://dx.doi.org/10.1002/med.2610010203
33 Fernandes GFS, Campos DL, Da Silva IC, Prates JLB, Pavan AR, Pavan FR, et al. (2021) ChemMedChem 16:1268–1282. http://dx.doi.org/10.1002/cmdc.202000899
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35 Chugunova E, Frenna V, Consiglio G, Micheletti G, Boga C, Akylbekov N, et al. (2020) J Org Chem 85:13472–13480. https://doi.org/10.1021/acs.joc.0c01502
36 Sema L Ioffe (2007) “Nitronates”, Nitrile Oxides Nitrones and Nitronates in Organic Synthesis. Ed. by Henry Feuer. A John Wiley & Sons, Inc., Publication, Canada.
37 Chugunova E, Micheletti G, Telese D, Boga C, Islamov D, Usachev K, et al. (2021) Int J Mol Sci 22:7497. https://doi.org/10.3390/ijms22147497
38 Ustyuzhanina NE, Fershtat LL, Gening ML, Nifantiev NE, Makhova NN (2016) Mendeleev Commun 26:513–515. https://doi.org/10.1016/j.mencom.2016.11.018
39 Orlandi VT, Bolognese F, Rolando B, Guglielmo S, Lazzarato L, Fruttero R (2018) Microbiology 164:1557–1566. https://doi.org/10.1099/mic.0.000730
40 Fei Y, Wu J, An H-W, Zhu K, Peng B, Cai J, et al. (2020) J Med Chem 63:9127–9135. https://doi.org/10.1021/acs.jmedchem.9b01832
41 Huang LY, Tsui DY, Williams CM, Wyse BD, Smith MT (2015) Clin Exp Pharmacol Physiol 42:921–929. http://dx.doi.org/10.1111/1440-1681.12442
42 Makhova NN, Fershtat LL (2018) Tetrahedron Lett 59:2317–2326. http://dx.doi.org/10.1016/j.tetlet.2018.04.070
43 Pippin AB, Mohd Arshad ZH, Voll RJ, Nye JA, Ghassabian S, Williams CM, et al. (2016) ACS Med Chem Lett 7:563–567. http://dx.doi.org/10.1021/acsmedchemlett.5b00410
44 Huang L, Wyse BD, Williams CM, Smith MT (2019) Clin Exp Pharmacol Physiol 46:676–685. http://dx.doi.org/10.1111/1440-1681.13091
45 Schiefer IT, VandeVrede L, Fa’ M, Arancio O, Thatcher GRJ (2012) J Med Chem 55:3076–3087. http://dx.doi.org/10.1021/jm201504s
46 de Carvalho PS, Maróstica M, Gambero A, Pedrazzoli J (2010) Eur J Med Chem 45:2489–2493. http://dx.doi.org/10.1016/j.ejmech.2010.02.034
47 Chugunova E, Matveeva V, Tulesinova A, Iskanderov E, Akylbekov N, Dobrynin A, et al. (2022)Int J Mol Sci. http://dx.doi.org/10.3390/ijms232314902
48 Chugunova EA, Burilov AR (2017) Curr Top Med Chem 17:986–1005. http://dx.doi.org/10.2174/1568026616666160927145822
49 dos Santos Fernandes GF, de Souza PC, Marino LB, Chegaev K, Guglielmo S, Lazzarato L, et al. (2016) Eur J Med Chem 123:523–531. http://dx.doi.org/https://doi.org/10.1016/j.ejmech.2016.07.039
50 Zhang Z, Bai Z-W, Ling Y, He L-Q, Huang P, Gu H-X, et al. (2018) Med Chem Res 27:1198–1205. http://dx.doi.org/10.1007/s00044-018-2140-x
51 Abdelall EKA (2020) Bioorg Chem 94:103441. http://dx.doi.org/https://doi.org/10.1016/j.bioorg.2019.103441
52 Fershtat L, Bystrov D, Zhilin E, Makhova N (2019) Synthesis (Stuttg) 51:747–756. http://dx.doi.org/10.1055/s-0037-1611056
53 Chugunova E, Gibadullina E, Matylitsky K, Bazarbayev B, Neganova M, Volcho K, et al. (2023) Pharmaceuticals 16:499. http://dx.doi.org/10.3390/ph16040499
54 Sotgia F, Martinez-Outschoorn UE, Lisanti MP (2011) BMC Med 9:62. https://doi.org/10.1186/1741-7015-9-62
55 Smolobochkin A, Gazizov A, Sazykina M, Akylbekov N, Chugunova E, Sazykin I, et al. (2019) Molecules 24:3086. https://doi.org/10.3390/molecules24173086
56 Chugunova E, Matveeva V, Tulesinova A, Iskanderov E, Akylbekov N, Dobrynin A, et al. (2022) Int J Mol Sci 23:14902. https://doi.org/10.3390/ijms232314902
57 Khan FH, Dervan E, Bhattacharyya DD, McAuliffe JD, Miranda KM, Glynn SA (2020) Int J Mol Sci 21:9393. https://doi.org/10.3390/ijms21249393
58 Shpakovsky DB, Banti CN, Mukhatova EM, Gracheva YA, Osipova VP, Berberova NT, et al. (2014) Dalt Trans 43:6880–6890. https://doi.org/10.1039/C3DT53469C
59 Wang L, Li C, Zhang Y, Qiao C (2013) J Agric Food Chem 61:8632−8640. https://doi.org/10.1021/jf402388x
60 Bogdanov AV, Iskhakova KR, Voloshina AD, Sapunova AS, Kulik NV, Terekhova NV, et al. (2020) Chem Biodivers 17: e2000147. https://doi.org/10.1002/cbdv.202000147
61 de Giacometi M, Mayer JCP, de Mello AB, Islabão YW, Strothmann AL, da Fonseca RN, et al. (2023) Exp Parasitol 253:108601. https://doi.org/10.1016/j.exppara.2023.108601
62 Gala UH, Miller DA, Williams RO (2020) Biochim Biophys Acta - Rev Cancer 1873:188319. https://doi.org/10.1016/j.bbcan.2019.188319
63 DIMITRIOS B (2006) Trends Food Sci Technol 17:505–512. https://doi.org/10.1016/j.tifs.2006.04.004
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Published
2025-04-05
How to Cite
ZhаnаkоvM., Zhatkanbayeva, Z., СhugunоvаE., Akylbekov, N., & ZhаtkаnbауеvY. (2025). Mіnі-rеvіеw: Advаnсеs іn thе sуnthеsіs аnd bіоlоgісаl асtіvіtу оf bеnzоfurохаn аnd furохаn dеrіvаtіvеs. Chemical Bulletin of Kazakh National University, 114(1). https://doi.org/https://doi.org/10.15328/cb1391
Section
Organic and Polymers Chemistry
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